List of benzodiazepines

The tables below contain a sample list of benzodiazepines and benzodiazepine analogs that are commonly prescribed, with their basic pharmacological characteristics, such as half-life and equivalent doses to other benzodiazepines, also listed, along with their trade names and primary uses. The elimination half-life is how long it takes for half of the drug to be eliminated by the body. "Time to peak" refers to when maximum levels of the drug in the blood occur after a given dose. Benzodiazepines generally share the same pharmacological properties, such as anxiolytic, sedative, hypnotic, skeletal muscle relaxant, amnesic, and anticonvulsant effects. Variation in potency of certain effects may exist amongst individual benzodiazepines. Some benzodiazepines produce active metabolites. Active metabolites are produced when a person's body metabolizes the drug into compounds that share a similar pharmacological profile to the parent compound and thus are relevant when calculating how long the pharmacological effects of a drug will last. Long-acting benzodiazepines with long-acting active metabolites, such as diazepam and chlordiazepoxide, are often prescribed for benzodiazepine or alcohol withdrawal as well as for anxiety if constant dose levels are required throughout the day. Shorter-acting benzodiazepines are often preferred for insomnia due to their lesser hangover effect.^{[1][2][3][4][5]}

It is fairly important to note that elimination half-life of diazepam and chlordiazepoxide, as well as other long half-life benzodiazepines, is twice as long in the elderly compared to younger individuals. Due to increased sensitivity and potentially dangerous adverse events among elderly patients, it is recommended to avoid prescribing them as specified by the 2015 American Geriatrics Society Beers Criteria.^[6] Individuals with an impaired liver also metabolize benzodiazepines more slowly. Thus, the approximate equivalent of doses below may need to be adjusted accordingly in individuals on short acting benzodiazepines who metabolize long-acting benzodiazepines more slowly and vice versa. The changes are most notable with long acting benzodiazepines as these are prone to significant accumulation in such individuals and can lead to withdrawal symptoms.^{[citation needed]} For example, the equivalent dose of diazepam in an elderly individual on lorazepam may be half of what would be expected in a younger individual.^[7][8] Equivalent doses of benzodiazepines differ as much as 20 fold.^[9][10][11]

Pharmacokinetic properties of various benzodiazepines

Equivalency data in the table below is taken from the Ashton "Benzodiazepine Equivalence Table".^{[4][12][13][14]}

Drug Name	Common Trade Names[a]	Year Approved (US FDA)	Typical Oral Dosage Formulations (mg)	Approx. Equivalent Oral Dose to 10 mg Diazepam[b] (mg)	Peak Onset of Action (hours)	Elimination Half-life of Active Metabolite (hours)	Primary Therapeutic Use
Adinazolam	Deracyn	Research chemical			1–2	3	anxiolytic, antidepressant
Alprazolam	Xanax, Helex, Xanor, Trankimazin, Onax, Alprox, Misar, Restyl, Solanax, Tafil, Neurol, Frontin, Kalma, Ksalol, Farmapram	1981	0.25, 0.5, 1, 2	0.5	1–3[16]	11-13 [10–20][16]	anxiolytic, antidepressant[17]
Bentazepam[c]	Thiadipona		25		1–3	2–4	anxiolytic
Bretazenil[18]						2.5	anxiolytic, anticonvulsant
Bromazepam	Lexotanil, Lexotan, Lexilium, Lectopam, Lexaurin, Lexatin, Bromam	1981	1.5, 3, 6	6	1–5	20–40	anxiolytic, hypnotic, muscle relaxant
Bromazolam		Research chemical	2 , 4	2			anxiolytic
Brotizolam[d]	Lendormin, Dormex, Sintonal, Noctilan		0.25	0.5	0.5–2	4–5	hypnotic
Camazepam	Albego, Limpidon			40[19]	1–3	6–11	anxiolytic
Chlordiazepoxide	Librium, Risolid, Elenium	1960	5, 10, 25	25	1.5–6	36–200	anxiolytic
Cinazepam	Levana		0.5, 1, 2		2–4	60	hypnotic, anxiolytic
Cinolazepam	Gerodorm		40		0.5–2	9	hypnotic
Clobazam	Onfi, Frisium, Urbanol	2011	5, 10, 20	20	1–5	8–60	anxiolytic, anticonvulsant
Clonazepam	Rivatril, Rivotril, Klonopin, Iktorivil, Paxam	1975	0.5, 1, 2	0.5-1	1–5	19.5–50	anticonvulsant, anxiolytic
Clonazolam		Research chemical	0.25, 0.5	0.2	0.5-1	3-4[20]	hypnotic, anticonvulsant
Clorazepate	Tranxene, Tranxilium	1972	3.75, 5, 7.5	15	Variable	32–152	anxiolytic, anticonvulsant
Clotiazepam[c]	Veratran, Clozan, Rize		5, 10	10	1–3	4	anxiolytic
Cloxazolam	Cloxam, Sepazon, Olcadil		1, 2, 4	1.5[19]	2–5	55–77[19]	anxiolytic, anticonvulsant
Delorazepam	Dadumir		0.5, 1, 2	1-1.5	1–2	79<[21]	anxiolytic, amnesic
Deschloroetizolam[d]		Research chemical	1, 2	4			anxiolytic
Diazepam	Antenex, Apaurin, Apzepam, Apozepam, Diazepan, Hexalid, Normabel, Pax, Stesolid, Stedon, Tranquirit, Valium, Vival, Valaxona	1963	2, 5, 10	10	1–1.5	32–205	anxiolytic, anticonvulsant, muscle relaxant, amnesic
Diclazepam[22]		Research chemical	1, 2	2	1.5–3	42	anxiolytic, muscle relaxant
Estazolam	ProSom, Nuctalon	1990	1, 2	2[19]	3–5	10–24	hypnotic, anxiolytic
Ethyl carfluzepate		Not approved		2	1–5	11–24	hypnotic
Etizolam[d]	Etilaam, Etizest, Pasaden, Depas	Often sold as a research chemical, but is approved for human use in many countries. Controlled substance in some US states, Canada, Germany, Austria, and others.[23][24]	1	2	1–3	5-7	anxiolytic, muscle relaxant, anticonvulsant
Ethyl loflazepate	Victan, Meilax, Ronlax			2[19]	2.5–3	73–119	anxiolytic
Flualprazolam		Research chemical	0.5, 1	0.25	1-2	12-22	anxiolytic, hypnotic
Flubromazepam[25]	Templex	Research chemical	4, 8, 12	4	1.5–8	100–220	anxiolytic, hypnotic, amnesic, muscle relaxant, anticonvulsant
Flubromazolam	Remnon	Research chemical	0.25, 0.5	0.075	0.5-5	10-20[26]	hypnotic
Fluclotizolam[d]		Research chemical		0.25-0.5			anxiolytic
Flunitrazepam	Rohypnol, Hipnosedon, Vulbegal, Fluscand, Flunipam, Ronal, Rohydorm, Hypnodorm	1972	1, 2	1.5	0.5–3	18–200	hypnotic
Flunitrazolam		Research chemical	0.25, 0.5	0.1	0.5-1	5-13	hypnotic
Flurazepam	Dalmadorm, Dalmane, Fluzepam	1970	30	20-25	1–1.5	40–250	hypnotic
Flutazolam	Coreminal		4	10	1-3	47-100	hypnotic
Flutemazepam		Research chemical		1	0.5-5	8-20	hypnotic, anxiolytic, anticonvulsant, muscle relaxant[27]
Flutoprazepam	Restas	1984	1, 2	2.5	0.5–9	87[28]	hypnotic, anticonvulsant, muscle relaxant
Halazepam	Alapryl, Paxipam	1981	20, 40	40	3–6	15-35 [30-100]	anxiolytic
Ketazolam	Anxon, Sedotime	1980	15, 30, 45	20	2.5–6	30-100 [36-200]	anxiolytic
Loprazolam	Dormonoct, Havlane	1983	1, 2	1.5	2–5	6–20[29]	hypnotic
Lorazepam	Ativan, Orfidal, Lorenin, Lorsilan, Temesta, Tavor, Lorabenz	1977	0.5, 1, 2, 2.5	1	2–4	10–20	anxiolytic, anticonvulsant, hypnotic, muscle relaxant[30][14][31]
Lormetazepam	Loramet, Noctamid, Pronoctan	1984	1, 2	1.5	0.5–2	10-12	hypnotic, anxiolytic
Meclonazepam		Research chemical	6				anxiolytic
Medazepam	Nobrium, Ansilan, Mezapam, Rudotel, Raporan		10	10	4-8	36–200	anxiolytic
Metizolam[d]		Research chemical	1, 2, 4	2–4		12	anxiolytic
Mexazolam	Melex, Sedoxil		0.5, 1		1–2		anxiolytic
Midazolam	Dormicum, Flormidal, Versed, Hypnovel, Dormonid	1985	7.5, 15	10 (oral) 4 (IV)	0.5–1	1.8-6	hypnotic, anticonvulsant
Nifoxipam		Research chemical	0.5, 1, 2				hypnotic
Nimetazepam	Erimin, Lavol	1984	5	2.5-5	0.5–3	14–30	hypnotic
Nitemazepam		Research chemical		2	0.5-5	10-27	hypnotic, anticonvulsant
Nitrazepam	Mogadon, Alodorm, Pacisyn, Dumolid, Nitrazadon	1965	5, 10	5	0.5–7	17–48	hypnotic, anticonvulsant
Nitrazolam		Research chemical	0.5, 1				hypnotic
Nordazepam	Madar, Stilny		5, 7.5, 15	10-15		30–150	anxiolytic
Norflurazepam		Research chemical		5		47-100	hypnotic
Oxazepam	Seresta, Serax, Serenid, Serepax, Sobril, Oxabenz, Oxapax, Oxascand, Ox-Pam, Opamox, Alepam, Medopam, Murelax, Noripam, Purata	1965	10, 15, 30, 50	30	3–4	4–11	anxiolytic
Phenazepam	Phenazepam, Phenzitat	Research chemical			1.5–4	60	anxiolytic, anticonvulsant
Pinazepam	Domar, Duna		5, 10			40–100	anxiolytic
Prazepam	Demetrin, Lysanxia, Prazene, Centrax	1976	10, 20, 30	15-20	2–6	36–200	anxiolytic
Premazepam		Not approved		15	2–6	10–13	anxiolytic
Pyrazolam		Research chemical	0.25, 0.5, 1		1–1.5	16–18[32]	anxiolytic, amnesic
Quazepam	Doral, Quiedorm	1985	15	20	1–5	39–120	hypnotic
Rilmazafone	Rhythmy					11	hypnotic
Temazepam	Restoril, Normison, Euhypnos, Temaze, Tenox	1981	10, 20	15-20	0.5–3	4–11	hypnotic, anxiolytic, muscle relaxant
Tetrazepam	Myolastan, Clinoxam, Epsipam, Musaril		50		1–3	3–26	muscle relaxant, anxiolytic
Triazolam	Halcion, Rilamir, Notison, Somese	1980	0.125, 0.25	0.5	0.5–2	2	hypnotic
Drug Name	Common Trade Names	Year Approved	Typical Dosages of Oral Tablets (mg)	Approx. Equivalent Oral Dose to 10mg Diazepam (mg)	Peak onset of action (hours)	Elimination Half-life of Active Metabolite (hours)	Primary Therapeutic Use

Atypical benzodiazepine receptor ligands

Drug Name	Common Trade Names	Year approved (US FDA)	Elimination Half-life of Active Metabolite (hours)	Primary Therapeutic Use
DMCM				anxiogenic, convulsant
Flumazenil[e]	Anexate, Lanexat, Mazicon, Romazicon		1	antidote
Eszopiclone§	Lunesta	2004	6	hypnotic
Zaleplon§	Sonata, Starnoc	1999	1	hypnotic
Zolpidem§	Ambien, Nytamel, Sanval, Stilnoct, Stilnox, Sublinox (Canada), Xolnox, Zoldem, Zolnod	1992	2.6	hypnotic
Zopiclone§	Imovane, Rhovane, Ximovan; Zileze; Zimoclone; Zimovane; Zopitan; Zorclone, Zopiklone		4–6	hypnotic

1. Not all trade names are listed.
2. An alternative table published by the state of South Australia uses equivalent approximate oral dosages to 5 mg diazepam.^[15]
3. Technically this is a thienodiazepine, but produces very similar effects as benzodiazepines.
4. Technically this is a thienotriazolodiazepine, but produces very similar effects as benzodiazepines.
5. Flumazenil is an imidazobenzodiazepine derivative,^[33] and in layman's terms, it is a benzodiazepine overdose antidote that is given intravenously in Intensive Care Units (ICUs) to reverse the effects of benzodiazepine overdoses, as well for overdoses of the non-benzodiazepine "Z-drugs" such as zolpidem.^[34] Flumazenil is contraindicated for benzodiazepine-tolerant patients in overdose cases.^[34] In such cases, the benefits are far outweighed by the risks, which include potential and severe seizures.^[33][35] The method by which flumazenil acts to prevent non-benzodiazepine tolerant overdose from causing potential harm is via preventing the benzodiazepines and Z-drugs from binding to the GABA_A receptors via competitive inhibition which the flumazenil creates. Clinical observation notating the patient's oxygen levels, respiratory, heart and blood pressure rates are used, as they are much safer than the potential seizure effects from flumazenil. Supportive care to mediate any problems resulting from abnormal rates of the pulmonary, respiratory, and cardiovascular systems is typically the only treatment that is required in benzodiazepine-only overdoses.^[36] In most cases, activated charcoal/carbon is often used to prevent benzodiazepines from being absorbed by the gastrointestinal tract, and the use of stomach-pumping/gastric lavage is no longer commonly used nor suggested by some toxicologists.^[37] Even in cases where other central nervous system (CNS) depressants (such as in combined benzodiazepine and tricyclic antidepressant/TCA overdoses) are detected and/or suspected, endotrachial intubation for the airway path and supportive oxygen are typically implemented and are much safer than flumazenil.^[36]

Controversy

In 2015 the UK's House of Commons attempted to get a two to four week limit mandate for prescribing benzodiazepines to replace the two to four week benzodiazepine prescribing guidelines, which are merely recommended.^[38]

Binding data and structure-activity relationship

A variety of Benzodiazepines along with their molecular structure.

A large number of benzodiazepine derivatives have been synthesised and their structure-activity relationships explored in detail.^{[39][40][41][42]} This chart contains binding data for benzodiazepines and related drugs investigated by Roche up to the late 1990s (though in some cases the compounds were originally synthesised by other companies such as Takeda or Upjohn).^{[43][44][45][46][47][48]} Other benzodiazepines are also listed for comparison purposes,^[49][50][51] but it does not however include binding data for;

• Benzodiazepines developed in the former Soviet Union (e.g. phenazepam, gidazepam etc.)
• Benzodiazepines predominantly used only in Japan (e.g. nimetazepam, flutoprazepam etc.)
• 4,5-cyclised benzodiazepines (e.g. ketazolam, cloxazolam etc.), and other compounds not researched by Roche
• Benzodiazepines developed more recently (e.g. remimazolam, QH-ii-066, Ro48-6791 etc.)
• "Designer" benzodiazepines for which in vitro binding data are unavailable (e.g. flubromazolam, pyrazolam etc.)^{[52][53][54][55][56]}

While binding or activity data are available for most of these compounds also, the assay conditions vary between sources, meaning that in many cases the values are not suitable for a direct comparison. Many older sources used animal measures of activity (i.e. sedation or anticonvulsant activity) but did not measure in vitro binding to benzodiazepine receptors.^[57][58] See for instance Table 2 vs Table 11 in the Chem Rev paper, Table 2 lists in vitro pIC₅₀ values matching those below, while Table 11 has pEC₅₀ values derived from in vivo assays in mice, which show the same activity trends but cannot be compared directly, and includes data for compounds such as diclazepam and flubromazepam which are not available in the main data set.

Also note;

• IC₅₀ / pIC₅₀ values represent binding affinity only and do not reflect efficacy or pharmacokinetics, and some compounds listed are GABA_A antagonists rather than agonists (e.g. flumazenil).
• Low IC₅₀ or high pIC₅₀ values indicate tighter binding (pIC₅₀ of 8.0 = IC₅₀ of 10nM, pIC₅₀ of 9.0 = IC₅₀ of 1nM, etc.)
• These are non subtype selective IC₅₀ values averaged across all GABA_A receptor subtypes, so subtype selective compounds with strong binding at one subtype but weak at others will appear unusually weak due to averaging of binding values (see e.g. CL-218,872)
• ^† indicates a predicted value from in silico modelling.^[59]
• Finally, note that the benzodiazepine core is a privileged scaffold, which has been used to derive drugs with diverse activity that is not limited to the GABA_A modulatory action of the classical benzodiazepines,^[60] such as devazepide and tifluadom, however these have not been included in the list below. 2,3-benzodiazepines such as tofisopam are also not listed, as these act primarily as AMPA receptor modulators, and are inactive at GABA_A receptors.

Table

Table of benzodiazepines

Chemical structure Code pIC50 / IC50 Chemical name PubChem CAS number Ro05-3061 7.3979 / 40nM 7-fluoro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 75849 2648-00-2 Ro05-4865 7.7696 / 17nM 7-fluoro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366179 Ro05-6820 8.1308 / 7.4nM 7-fluoro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366116 Ro05-6822 8.2924 / 5.1nM 7-fluoro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275675 2024-34-2 Iso-flubromazepam 7-fluoro-5-(2-bromophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 15292433 153873-96-2 Nordazepam 8.0269 / 9.4nM 7-chloro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 2997 1088-11-5 Diazepam 8.0915 / 8.1nM 7-chloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3016 439-14-5 Norflurazepam (Ro05-3367) 8.699 7-chloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 4540 2886-65-9 Fludiazepam 7-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3369 3900-31-0 Ro07-3953 8.7959 / 1.6nM 7-chloro-5-(2,6-difluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275763 Difludiazepam (Ro07-4065) 8.3872 / 4.1nM 7-chloro-5-(2,6-difluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366236 39080-67-6 Delorazepam 8.7447 / 1.8nM 7-chloro-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 17925 2894-67-9 Diclazepam (Ro05-3448) 7.8 † 7-chloro-5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 76168 2894-68-0 Ro05-4864 TSPO ligand 7-chloro-5-(4-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 1688 14439-61-3 Ro07-5193 8.5229 7-chloro-5-(2-chloro-6-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366219 Ro22-3294 8.1549 7-chloro-5-(2,6-dichlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 12790028 Ro07-5220 8.2596 7-chloro-5-(2,6-dichlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 9975396 30144-88-8 7-BPDBD 7.8 † 7-bromo-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 76167 2894-61-3 QH-II-063 7-bromo-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 627432 28611-28-1 Phenazepam 8.4 † 7-bromo-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 40113 51753-57-2 Flubromazepam (JYI-42) 7.6 † 7-bromo-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 12947024 2647-50-9 Flubrometazepam 7-bromo-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 135809 86890-79-1 SH-I-048A (3S)-7-bromo-5-(2-fluorophenyl)-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 49850464 872874-11-8 Gidazepam 6.4 † 2-(7-bromo-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-1-yl)acetohydrazide 121919 129186-29-4 Ro13-3780 8.6198 7-bromo-5-(2,6-difluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 9975396 103380-73-0 Ro07-9749 7-iodo-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3082318 30843-56-2 Ro07-9957 8.5376 7-iodo-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 118749 Ro05-2904 7.8861 / 13nM 7-trifluoromethyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 16795 2285-16-7 Ro14-3074 8.2757 / 5.3nM 7-azido-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Nitrazepam 8.0 / 10nM 7-nitro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4506 146-22-5 Nimetazepam 7-nitro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4496 2011-67-8 Ro05-4435 8.829 / 1.5nM 7-nitro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 520217 2558-30-7 Flunitrazepam 8.4202 / 3.8nM 7-nitro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3380 1622-62-4 Clonazepam 8.7447 / 1.8nM 7-nitro-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 2802 1622-61-3 Ro05-4082 8.6576 7-nitro-5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 528222 5527-71-9 Ro05-3590 8.4559 / 3.5nM 7-nitro-5-[2-(trifluoromethyl)phenyl]-1H-benzo[e] [1,4]diazepin-2(3H)-one 15024 1427-45-8 QH-146 7-nitro-5-(2-nitrophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44383992 Ro20-7736 7.0177 / 96nM 7-hydroxyamino-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro05-3072 6.4134 / 386nM 7-amino-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 78641 4928-02-3 Ro05-4318 6.3372 / 460nM 7-amino-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275339 4959-16-4 Ro20-1815 7.1871 / 65nM 7-amino-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 92294 34084-50-9 Ro05-4619 7.1249 / 75nM 7-amino-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 188298 4959-17-5 Ro05-3308 IC50 >1000nM N-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-7-yl)acetamide Ro12-6377 7.1249 / 455nM 1-(5-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-benzo[e] [1,4]diazepin-7-yl)-3-methylurea Ro05-9090 IC50 >1000nM 7-(aminomethyl)-1-methyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro05-3343 IC50 >1000nM N,N-dimethyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepine-7-sulfonamide 214460 12037-79-5 Ro05-4528 6.4202 / 380nM 7-cyano-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-2541 7.5229 / 30nM 7-cyano-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-2533 7.4437 / 36nM 7-ethyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 10264786 Ro20-5747 7.6198 / 24nM 7-vinyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366036 QH-ii-066 7.4 † 7-ethynyl-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 9838431 183239-39-6 OMB-18 7-ethynyl-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 89276170 XLI-352 7-ethynyl-5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 21065236 Ro20-5397 7.3665 / 43nM 7-formyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-3053 7.7447 / 18nM 7-acetyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 21828109 Ro05-2921 6.4559 / 350nM 5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 76175 2898-08-0 Ro05-3663 IC50 >1000nM 5-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 5080 70656-87-0 Ro05-4336 7.6778 / 21nM 5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 13292074 Ro07-4419 7.7212 / 19nM 5-(2,6-difluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366255 Ro05-4520 7.8539 / 14nM 5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 193319 844-11-1 Ro05-4608 8.4202 5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 10469149 Ro05-3546 6.4949 / 320nM 6-chloro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 14590445 Ro13-0699 6.8239 / 150nM 6-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44377764 Ro07-6198 7.5528 / 28nM 8-chloro-5-(2,6-difluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275762 Ro20-8895 7.7212 / 19nM 8-methyl-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366169 Ro13-0593 7.1427 / 72nM 9-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro13-0882 IC50 300nM 6,8-dichloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro22-6762 7.3979 / 40nM 7,8-dichloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366089 Ro20-8065 8.4437 / 3.6nM 7,8-dichloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 10358803 88695-06-1 Ro20-8552 7.8539 / 14nM 7-methyl-8-chloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366138 Ro05-2750 7.4318 / 37nM 6,8-dichloro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro14-2312 IC50 >1000nM 6-amino-8-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro07-3609 7.284 Ro11-8125 7.4318 / 37nM 5-(2-chlorophenyl)-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one Ro08-6739 IC50 70nM 7-chloro-5-phenyl-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one Ro09-9212 8.4089 / 3.9nM 7-chloro-5-(2-chlorophenyl)-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one 135721042 Ro10-2643 IC50 9.4nM 7-chloro-5-(2-chlorophenyl)-1H-thieno[3,2-e] [1,4]diazepin-2(3H)-one Clotiazepam 7-ethyl-5-(2-chlorophenyl)-1-methyl-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one 2811 33671-46-4 Bentazepam 8.5 † 5-phenyl-3,5a,6,7,8,9-hexahydro-2H-[1]benzothieno[2,3-e] [1,4]diazepin-2(3H)-one 34592 29462-18-8 Lopirazepam 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-pyrido[3,2-e] [1,4]diazepin-2-one 68672 42863-81-0 Premazepam 6.7696 / 170nM 6,7-dimethyl-5-phenyl-3,7-dihydropyrrolo[3,4-e] [1,4]diazepin-2(1H)-one 72104 57435-86-6 Ripazepam 1-ethyl-3-methyl-8-phenyl-4,6-dihydropyrazolo[4,3-e] [1,4]diazepin-5(1H)-one 33474 26308-28-1 Zolazepam 1,3,8-trimethyl-4-(2-fluorophenyl)-6,8-dihydropyrazolo[3,4-e] [1,4]diazepin-7(1H)-one 35775 31352-82-6 Zomebazam 8.1 † 1,3,8-trimethyl-4-phenyl-6,8-dihydropyrazolo[4,3-b] [1,4]diazepine-5,7(1H,4H)-dione 132677 78466-70-3 Ro17-2221 6.585 / 260nM 1-(2-aminoethyl)-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro07-5096 IC50 >1000nM 2-(7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-benzo[e] [1,4]diazepin-1-yl)acetic acid Ro08-3026 7.2007 Halazepam 7.0362 / 92nM 7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 31640 23092-17-3 Quazepam 7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-thione 4999 36735-22-5 Fletazepam 7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1H-benzo[e] [1,4]diazepine 36834 34482-99-0 Pinazepam 7.0339 / 92.5nM 7-chloro-5-phenyl-1-(prop-2-yn-1-yl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 40391 52463-83-9 Prazepam IC50 110nM 7-chloro-5-phenyl-1-cyclopropylmethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4890 2955-38-6 Flutoprazepam 6.6 † 7-chloro-5-(2-fluorophenyl)-1-cyclopropylmethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3400 25967-29-7 Cloniprazepam 7.8 † 7-nitro-5-(2-chlorophenyl)-1-cyclopropylmethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-1310 6.2076 / 620nM 7-chloro-5-phenyl-1-(t-butyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Fosazepam 7-chloro-5-phenyl-1-(dimethylphosphorylmethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 37114 35322-07-7 Iclazepam 7-chloro-5-phenyl-1-[2-(cyclopropylmethoxy)ethyl]-1H-benzo[e] [1,4]diazepin-2(3H)-one 68777 57916-70-8 Tolufazepam 7-chloro-5-(2-chlorophenyl)-1-[2-(4-methylphenyl)sulfonylethyl]-1H-benzo[e] [1,4]diazepin-2(3H)-one 65647 86273-92-9 Elfazepam 6.9 † 7-chloro-5-(2-fluorophenyl)-1-(2-ethylsulfonylethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 65445 52042-01-0 Reclazepam 2-[7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]-1,3-oxazol-4(5H)-one 3052777 76053-16-2 Ro07-1986 8.0809 / 8.3nM 1-(2-aminoethyl)-7-chloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Flurazepam 7.8297 7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 3393 17617-23-1 Ro07-2750 7.6108 / 24.5nM 7-chloro-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Motrazepam IC50 430nM 1-(methoxymethyl)-7-nitro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 65764 29442-58-8 Ro08-9013 7.3716 Proflazepam 6.8539 / 140nM 7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3050433 52829-30-8 Ro22-4683 6.5229 / 300nM 7-nitro-5-(2-fluorophenyl)-1-(t-butyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro15-8852 6.1391 / 726nM 5-(2-chlorophenyl)-4-methyl-7-nitro-4,5-dihydro-1H-benzo[e] [1,4]diazepin-2(3H)-one Chlorodiazepoxide 6.4535 / 352nM 7-chloro-2-methylamino-5-phenyl-3H-benzo[e] [1,4]diazepine-4-oxide 2712 58-25-3 Cyprazepam 7-chloro-N-(cyclopropylmethyl)-4-hydroxy-5-phenyl-3H-benzo[e] [1,4]diazepin-2-imine 27452 15687-07-7 Uldazepam 7.6 † 7-chloro-5-(2-chlorophenyl)-N-prop-2-enoxy-3H-benzo[e] [1,4]diazepin-2-amine 34274 28546-58-9 Demoxepam 6.5086 / 310nM 7-chloro-1,3-dihydro-5-phenyl-2H-benzo[e] [1,4]diazepin-2-one-4-oxide 13756 963-39-3 Medazepam IC50 870nM 7-chloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepine 4041 2898-12-6 Tuclazepam 7.7 † 7-chloro-5-(2-chlorophenyl)-2-(hydroxymethyl)-1-methyl-2,3-dihydro-1H-benzo[e] [1,4]diazepine 3050405 51037-88-8 Metaclazepam 7-bromo-5-(2-chlorophenyl)-2-(methoxymethyl)-1-methyl-2,3-dihydro-1H-benzo[e] [1,4]diazepine 71272 84031-17-4 Sulazepam 7.7 † 7-chloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-thione 17931 2898-13-7 Tetrazepam 7.4685 / 34nM 7-chloro-5-(cyclohexen-1-yl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 25215 10379-14-3 Nortetrazepam IC50 34nM 7-chloro-5-(cyclohexen-1-yl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 166581 10379-11-0 Menitrazepam 7-nitro-5-(cyclohexen-1-yl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 189875 28781-64-8 Ro05-3328 7.0605 / 87nM 7-chloro-5-cyclohexyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Clazolam 8.1 † 2-chloro-5-methyl-5,9,10,14b-tetrahydroisoquino[2,1-d] [1,4]benzodiazepin-6(7H)-one 24107 7492-29-7 Bromazepam 7.7447 / 18nM 7-bromo-5-(pyridin-2-yl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 2441 1812-30-2 Methylbromazepam 7-bromo-5-(pyridin-2-yl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 630183 1812-33-5 Pyridazino-diazepam 7-chloro-5-(pyridazin-3-yl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one SCHEMBL9684958 7-chloro-5-(1H-pyrazol-5-yl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 21738192 Compound 6a 9.5 † 7-chloro-5-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one JC-184 7-bromo-5-(2-thienyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 21065240 BDBM50083903 7-chloro-5-(2-furanyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 10423506 Ro05-5605 6.5376 Ro11-3129 8.1871 (+)-2-amino-N-[2-(2-chlorobenzoyl)-4-nitrophenyl]propanamide 21413751 65607-70-7 Ro03-7355 6.3768 Ro11-4878 8.4559 / 3.5nM 7-chloro-5-(2-fluorophenyl)-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Meclonazepam 8.9208 / 1.2nM (3S)-7-nitro-5-(2-chlorophenyl)-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3033985 58662-84-3 Ro11-6896 8.1549 / 7nM 7-nitro-5-(2-fluorophenyl)-1,3-dimethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro06-7263 7.3098 / 49nM 1,7-dichloro-5-phenyl-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Oxazepam 7.7447 / 18nM 7-chloro-3-hydroxy-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4616 604-75-1 Temazepam 7.7959 / 16nM 7-chloro-3-hydroxy-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 5391 846-50-4 Lorazepam 8.4559 / 3.5nM 7-chloro-3-hydroxy-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3958 846-49-1 Lormetazepam 7-chloro-3-hydroxy-5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 13314 848-75-9 Flutemazepam 8.1 † 7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 40344 52391-89-6 Cinolazepam 7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-(2-cyanoethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3033621 75696-02-5 Doxefazepam 7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 38668 40762-15-0 Nifoxipam 8.5 † 7-nitro-3-hydroxy-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3058221 74723-10-7 Nitemazepam 7-nitro-3-hydroxy-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 12362353 40762-03-6 3-Hydroxyphenazepam 8.7 † 7-bromo-3-hydroxy-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 125820 70030-11-4 Cinazepam 7-bromo-3-succinyloxy-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 629281 172986-25-3 Pivoxazepam 7-chloro-3-pivalyloxy-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 68722 55299-10-0 Camazepam 6.0458 7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-3-yl N,N-dimethylcarbamate 37367 36104-80-0 Clorazepate IC50 59nM 7-chloro-2-oxo-5-phenyl-1H-benzo[e] [1,4]diazepine-3-carboxylic acid 2809 23887-31-2 Nitrazepate 7-nitro-2-oxo-5-phenyl-1H-benzo[e] [1,4]diazepine-3-carboxylic acid 21740 5571-84-6 Ethyl carfluzepate 8.0 † ethyl 7-chloro-5-(2-fluorophenyl)-1-(methylcarbamoyl)-2-oxo-3H-benzo[e] [1,4]diazepine-3-carboxylate 68856 65400-85-3 Ethyl dirazepate 7.5 † ethyl 7-chloro-5-(2-chlorophenyl)-2-oxo-3H-benzo[e] [1,4]diazepine-3-carboxylate 208941 23980-14-5 Ethyl loflazepate ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-3H-benzo[e] [1,4]diazepine-3-carboxylate 3299 29177-84-2 Carburazepam 7.9 † 7-chloro-1-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4H-benzo[e] [1,4]diazepine-4-carboxamide 68787 59009-93-7 Ro20-7078 8.2757 / 5.3nM 3,7-dichloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Clobazam 6.8861 / 130nM 7-chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 2789 22316-47-8 Desmethylclobazam 6.6778 / 210nM 7-chloro-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione Triflubazam 8.4 † 7-trifluoromethyl-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 2789 22316-47-8 Lofendazam 7-chloro-5-phenyl-1,3,4,5-tetrahydro-4H-1,5-benzodiazepin-4-one 71709 29176-29-2 Arfendazam 8.3 † ethyl 7-chloro-4-oxo-5-phenyl-2,3-dihydro-1,5-benzodiazepine-1-carboxylate 65803 37669-57-1 CP-1414S 7.9 † 8-nitro-1-phenyl-4-amino-3H-1,5-benzodiazepin-2-one 37594 36975-99-2 Compound 6i 8.6 † 9-chloro-11-phenyl-6,11-dihydro-5H-pyrimido[4,5-b][1,5]benzodiazepin-5-one Oxazolam 10-chloro-2-methyl-11b-phenyl-2,3,7,11b-tetrahydrobenzo[f]oxazolo[3,2-d] [1,4]diazepin-6(5H)-one 62779 24143-17-7 Cloxazolam 10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 2816 24166-13-0 Mexazolam 10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,7,11b-tetrahydro[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 4177 31868-18-5 Flutazolam 10-chloro-11b-(2-fluorophenyl)-7-(2-hydroxyethyl)-3,5-dihydro-2H-[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 3398 27060-91-9 Haloxazolam 10-bromo-11b-(2-fluorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 3563 59128-97-1 Ketazolam 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-[1,3]oxazino[3,2-d] [1,4]benzodiazepine-4,7(6H)-dione 33746 27223-35-4 U-35005 8.3665 / 4.3nM 6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21680194 4'-Chlorodeschloroalprazolam 6-(4-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine 142641556 92262-72-1 Estazolam 8.0706 / 8.5nM 8-chloro-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3261 29975-16-4 Alprazolam 7.699 / 20nM 8-chloro-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 2118 28981-97-7 Triazolam 8.3979 / 4nM 8-chloro-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 5556 28911-01-5 alpha-Hydroxytriazolam 8.3768 / 4.2nM 8-chloro-6-(2-chlorophenyl)-1-hydroxymethyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 1963 37115-45-0 Flualprazolam 8.3 † 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 10359044 28910-91-0 Iso-flualprazolam 8-fluoro-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine Desmethyltriazolam 8.3 † 8-chloro-6-(2-chlorophenyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 826660 42292-42-2 Nitrazolam 8.5 † 8-nitro-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20317278 28910-99-8 Desmethylnitrazolam 8.8 † 8-nitro-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20317280 30858-58-3 Clonazolam 9.5 † 8-nitro-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12317881 33887-02-4 Flunitrazolam 8.8 † 8-nitro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 137700379 2243815-18-9 Flubromazolam (JYI-73) 8.8 † 8-bromo-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21930924 612526-40-6 Fluiodomazolam (BDBM50011621) 8-iodo-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 14851835 Triflumazolam (SCHEMBL7327294) 8-trifluoromethyl-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 19010444 28910-98-7 JYI-70 8-ethynyl-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 14851900 XLI-296 8-ethynyl-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 14851901 Clobromazolam (DM-II-90) 8.2 † 8-bromo-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 1032830 87213-50-1 Bromazolam (XLI-268) 8.5 † 8-bromo-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12562546 71368-80-4 Pyrazolam (SH-I-04) 8.1 † 8-bromo-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12562545 39243-02-2 Pyclazolam 8.2 † 8-chloro-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20368150 Pynazolam 9.4 † 8-nitro-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20368157 2034366-97-5 Pyeazolam (SH-TRI-108) 7.9 † 8-ethynyl-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 71811108 1349115-59-8 Adinazolam 6.8697 / 135nM 8-chloro-6-phenyl-1-(N,N-dimethylaminomethyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 37632 37115-32-5 U-42352 8-chloro-6-phenyl-1-(N-methylaminomethyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 119094 37115-33-6 Fluadinazolam 7.1 † 8-chloro-6-(2-fluorophenyl)-1-(N,N-dimethylaminomethyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21537253 37391-59-6 U-43465 F 7.9431 8-chloro-1-[2-(dimethylamino) ethyl]-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine 134388 83983-74-8 Ro11-5073 8.4815 / 3.3nM (4S)-8-chloro-6-(2-fluorophenyl)-1,4-dimethyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 101637147 Ro11-6679 8.3979 / 4nM 8-nitro-6-(2-fluorophenyl)-1,4-dimethyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine Ro17-4582 8.4559 / 3.5nM 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine Etizolam 8.5086 / 3.1nM 2-ethyl-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3307 40054-69-1 Deschloroetizolam 8.5 † 2-ethyl-4-phenyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 827322 40054-73-7 Desmethyletizolam 2-ethyl-4-(2-chlorophenyl)-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12434325 40054-68-0 Fluetizolam 8.8 † 2-ethyl-4-(2-fluorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12434320 40054-88-4 Nitizolam 2-nitro-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 70600959 Iprotizolam 2-isopropyl-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 67727941 Clotizolam (Ro11-1465) 8.8539 / 1.4nM 2-chloro-4-(2-chlorophenyl)-9-methyl-4H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3041455 54123-06-7 Deschloroclotizolam 2-chloro-4-phenyl-9-methyl-4H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 157010678 1629324-97-5 Fluclotizolam 9.1 † 2-chloro-4-(2-fluorophenyl)-9-methyl-4H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21317700 54123-15-8 Difluclotizolam 2-chloro-4-(2,6-difluorophenyl)-9-methyl-4H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21317683 Brotizolam 8.9208 2-bromo-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 2451 57801-81-7 Flubrotizolam (LS-152,574) 9.6 † 2-bromo-4-(2-fluorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3044878 57801-95-3 Ro14-1636 8.8239 2-iodo-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 14851924 Ciclotizolam 8.0 † 2-bromo-4-(2-chlorophenyl)-9-cyclohexyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 71949 58765-21-2 Ro11-7800 8.5376 / 2.9nM (2-chloro-4-(2-chlorophenyl)-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-yl)methanamine Zapizolam 8.8 † 8-chloro-6-(2-chlorophenyl)-4H-pyrido[2,3-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 68832 64098-32-4 Rilmazolam (LS-188,599) 7.3 † 8-chloro-6-(2-chlorophenyl)-N,N-dimethyl-4H-1,2,4-triazolo[1,5-a] [1,4]benzodiazepine-2-carboxamide 148494 50330-59-1 Midazolam 8.3188 / 4.8nM 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a] [1,4]benzodiazepine 4192 59467-70-8 alpha-Hydroxymidazolam 8.3468 / 4.5nM 8-chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4H-imidazo[1,5-a] [1,4]benzodiazepine 107917 59468-90-5 Ro22-0284 8-chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4-hydroxy-4H-imidazo[1,5-a] [1,4]benzodiazepine 10316307 64740-68-7 Climazolam 8.1 † 8-chloro-6-(2-chlorophenyl)-1-methyl-4H-imidazo[1,5-a] [1,4]benzodiazepine 68790 59467-77-5 Remimazolam 8.3 † methyl 3-[(4S)-8-bromo-1-methyl-6-(pyridin-2-yl)-4H-imidazo[1,2-a] [1,4]benzodiazepin-4-yl]propanoate 9824461 308242-62-8 Ro15-8670 7.8239 / 15nM ethyl 8-chloro-6-phenyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 14907889 JYI-32 ethyl 8-bromo-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 21930922 JY-XHE-057 ethyl 8-ethynyl-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 21065283 Ro16-0529 7.8539 / 14nM tert-butyl 7-chloro-6-phenyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro21-5205 8.1308 / 7.4nM methyl 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 12801973 SH-053-R-CH3-2'F 7.9 † ethyl (4R)-8-ethynyl-6-(2-fluorophenyl)-4-methyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 11574585 872874-14-1 HZ-166 ethyl 8-ethynyl-6-(pyridin-2-yl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10309028 612527-56-7 MP-III-022 9.1 † (4R)-8-ethynyl-6-(2-fluorophenyl)-N,4-dimethyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 130439777 GL-II-73 (4R)-8-ethynyl-6-(2-fluorophenyl)-N,N,4-trimethyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 130439778 YT-III-31 8-ethynyl-6-phenyl-N-methyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 49848318 Ro22-1892 7.9208 / 12nM 8-chloro-6-(2-fluorophenyl)-3-(isopropoxycarbonyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine 5-oxide Ro22-0992 7.8861 / 13nM 8-chloro-6-(2-chlorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylic acid Ro21-8137 8.4559 / 3.5nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide Ro21-8384 8.4202 8-chloro-6-(2-chlorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 162997 63176-94-3 Imidazenil 8.8 † 8-fluoro-6-(2-bromophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 119194 151271-08-8 Ro23-0364 6-(2-chlorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 194998 113066-25-4 Ro21-8482 7.585 / 26nM 8-chloro-6-(2-chlorophenyl)-1-[(dimethylamino)methyl]-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide Loprazolam 8.2007 (2Z)-6-(2-chlorophenyl)-2-[(4-methyl-1-piperazinyl)methylene]-8-nitro-2,4-dihydro-1H-imidazo[1,2-a] [1,4]benzodiazepin-1-one 3033860 61197-73-7 Fluloprazolam 8.0 † (2Z)-6-(2-fluorophenyl)-2-[(4-methyl-1-piperazinyl)methylene]-8-nitro-2,4-dihydro-1H-imidazo[1,2-a] [1,4]benzodiazepin-1-one 12371485 PS-I-35 (2Z)-6-phenyl-2-[(4-methyl-1-piperazinyl)methylene]-8-bromo-2,4-dihydro-1H-imidazo[1,2-a] [1,4]benzodiazepin-1-one 72660859 Ro14-1359 7.1549 / 70nM 7-chloro-5-(2-fluorophenyl)-1H-benzo[b]azepin-2(3H)-one Ro15-8867 7.6021 / 25nM 7-nitro-5-(2-chlorophenyl)-1H-benzo[b]azepin-2(3H)-one Ro14-7187 6.3872 / 410nM 1-methyl-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 85687871 Ro13-9868 7.3768 / 42nM 8-chloro-1-methyl-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine Ro14-5921 7.7212 / 19nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 20449965 Ro14-0304 8.1871 / 6.5nM 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 20449964 Ro14-2652 8.2518 / 5.6nM (8-chloro-6-(2-fluorophenyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepin-1-yl)methanamine Ro15-9270 8.301 / 5nM 6-(2-chlorophenyl)-1-methyl-8-nitro-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 20450010 Ro14-0609 7.6126 / 24.4nM 8-chloro-6-(2-fluorophenyl)-5,6-dihydro-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine Ro15-2201 8.8239 / 1.5nM methyl 6-phenyl-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro15-0791 8.6021 / 2.5nM ethyl 6-phenyl-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro15-2200 8.3768 / 4.2nM ethyl 6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro14-3929 7.7959 / 16nM ethyl 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro14-3930 7.8239 / 15nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxamide Ro14-5568 6.6383 / 230nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine Ro22-1274 7.1249 / 75nM 8-chloro-1-(2-fluorophenyl)-3H-benzo[c]azepine 13271760 89376-31-8 Ro22-1251 7.9586 / 11nM 9-chloro-2-methyl-7-phenyl-5H-benzo[c]pyrimido[4,5-e]azepine Ro22-1366 8.3979 / 4nM 9-chloro-7-(2-fluorophenyl)-2-methyl-5H-benzo[c]pyrimido[4,5-e]azepine Ro22-2038 8.5528 / 2.8nM 9-chloro-7-(2-fluorophenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-amine Ro22-3245 8.5528 / 2.8nM 9-chloro-7-(2-chlorophenyl)-5H-benzo[c]pyrimido[4,5-e]azepine Ro22-3148 6.3768 / 420nM 6-phenyl-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-3147 8.284 / 5.2nM 6-(2-chlorophenyl)-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-0780 7.9586 / 11nM 8-chloro-6-phenyl-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-2466 8.7212 / 1.9nM 8-chloro-6-(2-fluorophenyl)-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-2468 8.6021 Ro22-8515 8-chloro-6-(2-chlorophenyl)-1,4-dihydropyrrolo[3,4-d] [2]benzazepin-3(2H)-one 145981 Ro14-5974 8.1938 / 6.4nM (S)-ethyl 9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate 10041121 88552-32-3 Ro15-4941 8.7696 / 1.7nM (S)-ethyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro14-5975 7.2076 / 62nM (S)-ethyl 7-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3607 7.3372 / 46nM (S)-tert-butyl 8-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-6624 8 / 10nM (S)-tert-butyl 8-ethyl-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3774 8.4949 / 3.2nM (S)-tert-butyl 8-methyl-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-0071 8.4949 / 3.2nM (S)-tert-butyl 9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-5824 8.4685 / 3.4nM (S)-tert-butyl 8-(methylthio)-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-8912 8.2076 / 6.2nM (S)-tert-butyl 8-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-4261 8.1135 / 7.7nM (S)-tert-butyl 7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-0075 8.6021 Ro16-6127 8.5086 / 3.1nM (S)-tert-butyl 8-chloro-7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3058 7.0458 Bretazenil 8.6576 (S)-tert-butyl 8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate 107926 84379-13-5 EVT-201 7-chloro-3-(5-[(dimethylamino)methyl]-1,2,4-oxadiazol-3-yl)-5-methyl-4,5-dihydro-6H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9885841 308239-86-3 FG-8205 7-chloro-5-methyl-3-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 129710 122384-14-9 L-655,708 ethyl (13aS)-7-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate 5311203 130477-52-0 PWZ-029 8-chloro-3-(methoxymethyl)-5-methyl-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9971547 Ro48-6791 8-fluoro-5-methyl-3-(5-[(dipropylamino)methyl]-1,2,4-oxadiazol-3-yl)-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9953485 172407-17-9 Ro48-8684 8-fluoro-5-methyl-3-(5-[(dipropylamino)methyl]-1,3-oxazol-2-yl)-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9866317 Ro4882224 3,10-dichloro-9H-benzo[f]imidazo[1,5-a] [1,2,4]triazolo[1,5-d] [1,4]diazepine 11673720 Ro4938581 3-bromo-10-(difluoromethyl)-9H-benzo[f]imidazo[1,5-a] [1,2,4]triazolo[1,5-d] [1,4]diazepine 11624499 883093-10-5 Ro16-6605 8.6778 Ro16-6048 8.4815 / 3.3nM (S)-tert-butyl 9-oxo-8-(trifluoromethyl)-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-6950 8.5528 / 2.8nM (S)-tert-butyl 8-nitro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-4019 8.8539 / 1.4nM (S)-propyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3031 8.6021 / 2.5nM (S)-isopropyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-9906 8.7696 / 1.7nM (S)-allyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-7081 8.585 Ro16-7082 8.2007 / 6.3nM (S)-isobutyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-7083 8.5376 / 2.9nM (13aS)-sec-butyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-9918 8.6383 / 2.3nM (S)-cyclopropylmethyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-4020 8.585 Ro16-6654 8.3979 / 4nM (S)-cyclohexyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro17-3206 8.4685 Ro17-3207 8.284 Ro16-4021 8.8239 Ro17-1302 8.2757 / 5.3nM (S)-phenyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro15-2427 IC50 >1000nM 5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide Ro14-7437 8.5229 / 3nM ethyl 5-methyl-6-oxo-4H-imidazo[1,5-a] [1,4]benzodiazepine-3-carboxylate 127597 83210-63-3 Sarmazenil (Ro15-3505) 8.5686 / 2.7nM ethyl 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 71231 78771-13-8 Ro15-1310 8.1675 / 6.8nM ethyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 114888 78756-33-9 Ro15-1746 IC50 >1000nM ethyl 9-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro15-3237 IC50 >1000nM ethyl 10-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro15-5623 8.699 Flumazenil 8.6021 ethyl 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 3373 78755-81-4 Ro15-4513 ethyl 8-azido-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 5081 91917-65-6 RY-031 ethyl 8-ethyl-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10245056 TG-4-29 ethyl 8-vinyl-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10591116 RY-080 ethyl 8-ethynyl-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 5311418 YT-II-76 ethyl 8-cyclopropyl-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 46214569 SVO-8-14 ethyl 8-allyl-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 15316982 SVO-8-30 ethyl 8-(furan-2-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 15316986 SVO-8-67 ethyl 8-phenyl-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 15316984 TG-4-39 ethyl 8-(thiophen-2-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 15316985 CD-214 cyclopropyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 101652266 DM-139 t-butyl 8-(pyrrolidin-1-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10547937 DM-146 t-butyl 8-(piperidin-1-yl)-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10834569 DM-173 t-butyl 8-(dimethylamino)-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10808192 DM-215 t-butyl 8-methoxy-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10807310 Ro19-4603 t-butyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepine-3-carboxylate 127382 99632-94-7 Iomazenil ethyl 7-iodo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10251042 127985-21-1 Ro17-9741 8.6198 / 2.4nM (S)-methyl 8-chloro-9-oxo-9,11,12,12a-tetrahydroazeto[1,2-a]benzo[e]imidazo[5,1-c] [1,4]diazepine-1-carboxylate Ro16-0858 8.8861 ethyl 8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[1,2-a]benzo[e]imidazo[5,1-c] [1,4]diazepine-1-carboxylate Ro16-0153 8.2757 tert-butyl 8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]benzo[e]imidazo[1,5-a] [1,4]diazepine-1-carboxylate Ro17-1812 8.8861 (S)-cyclopropylmethyl 8-chloro-9-oxo-9,11,12,12a-tetrahydroazeto[1,2-a]benzo[e]imidazo[5,1-c] [1,4]diazepine-1-carboxylate 146197 90450-01-4 Ro17-3211 8.62 Ro17-3401 9.0458 Ro17-3620 8.2924 Ro16-9351 8.4318 Ro16-9905 8.9208 Ro17-1338 9 Zopiclone 7.5086 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate 5735 43200-80-2 Suriclone 8.6778 [6-(7-chloro- 1,8-naphthyridin-2-yl)- 5-oxo- 3,7-dihydro- 2H-[1,4]dithiino[2,3-c]pyrrol- 7-yl]4-methylpiperazine- 1-carboxylate 40903 53813-83-5 CL-218,872 6.9208 3-methyl-6-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[3,4-f]pyridazine 107950 66548-69-4 GBLD-345 9 2-(4-aminophenyl)-3-methoxy-N-[(3-methoxyphenyl)methyl]imidazo[2,1-f]pyridazin-6-amine 4602899 122479-08-7

See also

• Benzodiazepine
• Benzodiazepine dependence
• Benzodiazepine withdrawal syndrome

References

1. Golombok S, Lader M (August 1984). "The psychopharmacological effects of premazepam, diazepam and placebo in healthy human subjects". British Journal of Clinical Pharmacology. 18 (2): 127–133. doi:10.1111/j.1365-2125.1984.tb02444.x. PMC 1463527. PMID 6148956.
2. de Visser SJ, van der Post JP, de Waal PP, Cornet F, Cohen AF, van Gerven JM (January 2003). "Biomarkers for the effects of benzodiazepines in healthy volunteers". British Journal of Clinical Pharmacology. 55 (1): 39–50. doi:10.1046/j.1365-2125.2002.t01-10-01714.x. PMC 1884188. PMID 12534639.
3. "Benzodiazepine Names". non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2009-04-05.
4. Ashton CH (March 2007). "Benzodiazepine Equivalence Table". benzo.org.uk. Retrieved 2009-04-05.
5. Hsiung R (July 1995). "Benzodiazepine Equivalence Charts". dr-bob.org. Archived from the original on 2009-02-09. Retrieved 2009-04-05.
6. By the American Geriatrics Society 2015 Beers Criteria Update Expert Panel; et al. (American Geriatrics Society 2015 Beers Criteria Update Expert Panel) (November 2015). "American Geriatrics Society 2015 Updated Beers Criteria for Potentially Inappropriate Medication Use in Older Adults". Journal of the American Geriatrics Society. 63 (11): 2227–2246. doi:10.1111/jgs.13702. PMID 26446832. S2CID 38797655.{{cite journal}}: CS1 maint: numeric names: authors list (link)
7. Salzman C (15 May 2004). Clinical geriatric psychopharmacology (4th ed.). USA: Lippincott Williams & Wilkins. pp. 450–453. ISBN 978-0-7817-4380-8.
8. Delcò F, Tchambaz L, Schlienger R, Drewe J, Krähenbühl S (2005). "Dose adjustment in patients with liver disease". Drug Safety. 28 (6): 529–545. doi:10.2165/00002018-200528060-00005. PMID 15924505. S2CID 9849818.
9. Riss J, Cloyd J, Gates J, Collins S (August 2008). "Benzodiazepines in epilepsy: pharmacology and pharmacokinetics". Acta Neurologica Scandinavica. 118 (2): 69–86. doi:10.1111/j.1600-0404.2008.01004.x. PMID 18384456. S2CID 24453988.
10. Ashton H (July 1994). "Guidelines for the rational use of benzodiazepines. When and what to use". Drugs. 48 (1): 25–40. doi:10.2165/00003495-199448010-00004. PMID 7525193. S2CID 46966796.
11. "benzo.org.uk : Benzodiazepines: How They Work & How to Withdraw, Prof C H Ashton DM, FRCP, 2002". benzo.org.uk. Retrieved 2019-12-19.
12. "Benzodiazepine Equivalence Chart". www.mental-health-today.com. Archived from the original on 30 January 2023.
13. "Benzodiazepine Equivalence Table". www.bcnc.org.uk. April 2007. Archived from the original on 2015-02-06.
14. Farinde A (31 July 2018). "Benzodiazepine Equivalency Table". Medscape.
15. "Benzodiazepines Information for GPs" (PDF). Drug and Alcohol Services South Australia.
16. Moylan S, Giorlando F, Nordfjærn T, Berk M (March 2012). "The role of alprazolam for the treatment of panic disorder in Australia". The Australian and New Zealand Journal of Psychiatry. 46 (3): 212–224. doi:10.1177/0004867411432074. PMID 22391278. S2CID 11006795.
17. Ashton Manual
18. van Steveninck AL, Gieschke R, Schoemaker RC, Roncari G, Tuk B, Pieters MS, et al. (June 1996). "Pharmacokinetic and pharmacodynamic interactions of bretazenil and diazepam with alcohol". British Journal of Clinical Pharmacology. 41 (6): 565–573. doi:10.1046/j.1365-2125.1996.38514.x. PMC 2042631. PMID 8799523.
19. "Benzodiazepine Names". non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2009-05-31.
20. N. Edinoff, Amber; A. Nix, Catherine; S. Odisho, Amira; P. Babin, Caroline; G. Derouen, Alyssa; C. Lutfallah, Salim; M. Cornett, Elyse; Murnane, Kevin S.; M. Kaye, Adam (22 August 2022). Müller, Thomas; Yamauchi, Junji (eds.). "Novel Designer Benzodiazepines: Comprehensive Review of Evolving Clinical and Adverse Effects". Neurology International. 14 (3): 652. doi:10.3390/neurolint14030053. PMC 9397074. PMID 35997362.
21. "NMS Labs Report" (PDF). NMS Labs. Retrieved 19 April 2022.
22. Moosmann B, Bisel P, Auwärter V (2014). "Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics". Drug Testing and Analysis. 6 (7–8): 757–763. doi:10.1002/dta.1628. PMID 24604775.
23. Health Santé Canada, Federal Government of Canada (January 20, 2012). "Status Decision of Controlled and Non-Controlled Substances" (PDF). Controlled Drugs and Substances Act. 1: 2.
24. Indiana General Assembly. "House Bill 1019 - Controlled substances". Indiana General Assembly. Retrieved 2018-02-22.
25. Moosmann B, Huppertz LM, Hutter M, Buchwald A, Ferlaino S, Auwärter V (November 2013). "Detection and identification of the designer benzodiazepine flubromazepam and preliminary data on its metabolism and pharmacokinetics". Journal of Mass Spectrometry. 48 (11): 1150–1159. Bibcode:2013JMSp...48.1150M. doi:10.1002/jms.3279. PMID 24259203.
26. Huppertz LM, Moosmann B, Auwärter V (January 2018). "Flubromazolam - Basic pharmacokinetic evaluation of a highly potent designer benzodiazepine". Drug Testing and Analysis. 10 (1): 206–211. doi:10.1002/dta.2203. PMID 28378533.
27. Esmailian M, Ahmadi O, Taheri M, Zamani M (September 2015). "Comparison of haloperidol and midazolam in restless management of patients referred to the Emergency Department: A double-blinded, randomized clinical trial". Journal of Research in Medical Sciences. 20 (9): 844–849. doi:10.1002/14651858.CD003079.pub4. PMC 6486117. PMID 29219171.
28. Barzaghi N, Leone L, Monteleone M, Tomasini G, Perucca E (1989). "Pharmacokinetics of flutoprazepam, a novel benzodiazepine drug, in normal subjects". European Journal of Drug Metabolism and Pharmacokinetics. 14 (4): 293–298. doi:10.1007/BF03190114. PMID 2633923. S2CID 20710732.
29. Swift CG, Swift MR, Ankier SI, Pidgen A, Robinson J (August 1985). "Single dose pharmacokinetics and pharmacodynamics of oral loprazolam in the elderly". British Journal of Clinical Pharmacology. 20 (2): 119–128. doi:10.1111/j.1365-2125.1985.tb05041.x. PMC 1400680. PMID 2864049.
30. Shah D, Borrensen D (2011). "Benzodiazepines: A Guide to Safe Prescribing" (PDF). The Carlat Report: Psychiatry. Archived from the original (PDF) on 2015-07-01. Retrieved 2015-06-28.
31. Vancouver Hospital Pharmaceutical Sciences. "Comparison of Benzodiazepines".
32. Moosmann B, Hutter M, Huppertz LM, Auwärter V. "Characterization of the designer benzodiazepines pyrazolam and flubromazepam and study on their detectability in human serum and urine samples" (PDF). Archived from the original (PDF) on 2014-11-05. Retrieved 2014-11-05.
33. "Romazicon 2 (flumazenil) 3 Injection" (PDF). Genentech, Inc.
34. "Flumazenil Injection, Solution [App Pharmaceuticals, Llc]". DailyMed. U.S. National Library of Medicine. Retrieved 2014-08-15.
35. Fleisher GR, Ludwig S, Silverman BK (2002). Synopsis of pediatric emergency medicine. Lippincott Williams & Wilkins. p. 409. ISBN 978-0-7817-3274-1.
36. "Toxicological analyses". Retrieved 21 March 2013.
37. Vale JA, Kulig K (2004). "Position paper: gastric lavage". Journal of Toxicology. Clinical Toxicology. 42 (7): 933–943. doi:10.1081/CLT-200045006. PMID 15641639. S2CID 29957973.
38. "APPG for Involuntary Tranquilliser Addiction". benzo.org.uk. Retrieved 21 March 2015.
39. Sternbach LH (January 1979). "The benzodiazepine story". Journal of Medicinal Chemistry. 22 (1): 1–7. doi:10.1021/jm00187a001. PMID 34039.
40. Hadjipavlou-Litina D, Hansch C (1994). "Quantitative structure-activity relationships of the benzodiazepines. a review and reevaluation". Chemical Reviews. 94 (6): 1483–1505. doi:10.1021/cr00030a002.
41. Edinoff AN, Nix CA, Odisho AS, Babin CP, Derouen AG, Lutfallah SC, Cornett EM, Murnane KS, Kaye AM, Kaye AD. Novel Designer Benzodiazepines: Comprehensive Review of Evolving Clinical and Adverse Effects. Neurol Int. 2022 Aug 22;14(3):648-663. doi:10.3390/neurolint14030053 PMID 35997362
42. Yu X, Greenblatt HK, Greenblatt DJ. Designer benzodiazepines: an update. Expert Rev Clin Pharmacol. 2023 Feb;16(2):109-117. doi:10.1080/17512433.2023.2170349 PMID 36649662
43. Haefely W, Kyburz E, Gerecke M, Mohler H (1985). "Recent advances in the molecular pharmacology of benzodiazepine receptors and in the structure-activity relationships of their agonists and antagonists". Adv. Drug Res. 1985 (14): 165–322.
44. Winkler DA, Burden FR, Watkins AJ (January 1998). "Atomistic Topological Indices Applied to Benzodiazepines using Various Regression Methods". Quantitative Structure-Activity Relationships. 17 (1): 14–19. doi:10.1002/(SICI)1521-3838(199801)17:01<14::AID-QSAR14>3.0.CO;2-U.
45. Thakur A, Thakur M, Khadikar P (November 2003). "Topological modeling of benzodiazepine receptor binding". Bioorganic & Medicinal Chemistry. 11 (23): 5203–5207. doi:10.1016/j.bmc.2003.08.014. PMID 14604684.
46. So SS, Karplus M (December 1996). "Genetic neural networks for quantitative structure-activity relationships: improvements and application of benzodiazepine affinity for benzodiazepine/GABAA receptors". Journal of Medicinal Chemistry. 39 (26): 5246–5256. doi:10.1021/jm960536o. PMID 8978853.
47. Braestrup C, Nielsen M (1983). "Benzodiazepine receptors. Biochemical Studies of CNS Receptors". In Iversen LL, Iversen SD, Snyder SH (eds.). Handbook of Psychopharmacology. Springer. ISBN 9781468443615.
48. Zhang W, Diaz-Arauzo H, Allen MS, Koehler KF, Cook JM (1996). "Chapter 7: Chemical and computer assisted development of the inclusive pharmacophore of benzodiazepine receptors.". In Choudhary MI (ed.). Studies in Medicinal Chemistry. CRC Press. p. 303. ISBN 9783718658794.
49. Obradović AL, Joksimović S, Poe MM, Ramerstorfer J, Varagic Z, Namjoshi O, et al. (March 2014). "Sh-I-048A, an in vitro non-selective super-agonist at the benzodiazepine site of GABAA receptors: the approximated activation of receptor subtypes may explain behavioral effects". Brain Research. 1554: 36–48. doi:10.1016/j.brainres.2014.01.036. PMC 3996760. PMID 24472579.
50. Cornett EM, Novitch MB, Brunk AJ, Davidson KS, Menard BL, Urman RD, Kaye AD (June 2018). "New benzodiazepines for sedation". Best Practice & Research. Clinical Anaesthesiology. 32 (2): 149–164. doi:10.1016/j.bpa.2018.06.007. PMID 30322456. S2CID 53501694.
51. Clayton T, Poe MM, Rallapalli S, Biawat P, Savić MM, Rowlett JK, et al. (2015). "A Review of the Updated Pharmacophore for the Alpha 5 GABA(A) Benzodiazepine Receptor Model". International Journal of Medicinal Chemistry. 2015: 430248. doi:10.1155/2015/430248. PMC 4657098. PMID 26682068.
52. Moosmann B, King LA, Auwärter V (June 2015). "Designer benzodiazepines: A new challenge". World Psychiatry. 14 (2): 248. doi:10.1002/wps.20236. PMC 4471986. PMID 26043347.
53. Moosmann B, Auwärter V (2018). "Designer Benzodiazepines: Another Class of New Psychoactive Substances". In Maurer H, Brandt S (eds.). New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 383–410. doi:10.1007/164_2018_154. ISBN 978-3-030-10560-0. PMID 30367253.
54. Manchester KR, Lomas EC, Waters L, Dempsey FC, Maskell PD (January 2018). "The emergence of new psychoactive substance (NPS) benzodiazepines: A review". Drug Testing and Analysis. 10 (1): 37–53. doi:10.1002/dta.2211. PMID 28471096.
55. Waters L, Manchester KR, Maskell PD, Haegeman C, Haider S (May 2018). "The use of a quantitative structure-activity relationship (QSAR) model to predict GABA-A receptor binding of newly emerging benzodiazepines". Science & Justice. 58 (3): 219–225. doi:10.1016/j.scijus.2017.12.004. PMID 29685303.
56. Zawilska JB, Wojcieszak J (July 2019). "An expanding world of new psychoactive substances-designer benzodiazepines". Neurotoxicology. 73: 8–16. doi:10.1016/j.neuro.2019.02.015. PMID 30802466. S2CID 73461430.
57. Blair T, Webb GA (September 1977). "Electronic factors in the structure-activity relationship of some 1,4-benzodiazepin-2-ones". Journal of Medicinal Chemistry. 20 (9): 1206–1210. doi:10.1021/jm00219a019. PMID 926122.
58. Biagi GL, Barbaro AM, Guerra MC, Babbini M, Gaiardi M, Bartoletti M, Borea PA (February 1980). "Rm values and structure-activity relationship of benzodiazepines". Journal of Medicinal Chemistry. 23 (2): 193–201. doi:10.1021/jm00176a016. PMID 7359533.
59. Catalani V, Floresta G, Botha M, Corkery JM, Guirguis A, Vento A, Abbate V, Schifano F. In silico studies on recreational drugs: 3D quantitative structure activity relationship prediction of classified and de novo designer benzodiazepines. Chem Biol Drug Des. 2023 Jan;101(1):40-51. doi:10.1111/cbdd.14119 PMID 35838189
60. Spencer J, Rathnam RP, Chowdhry BZ (September 2010). "1,4-Benzodiazepin-2-ones in medicinal chemistry". Future Medicinal Chemistry. 2 (9): 1441–1449. doi:10.4155/fmc.10.226. PMID 21426139.

Further reading

• Gitlow S (1 October 2006). Substance Use Disorders: A Practical Guide (2nd ed.). USA: Lippincott Williams and Wilkins. p. 110. ISBN 978-0-7817-6998-3.
• Galanter M, Kleber HD (1 July 2008). The American Psychiatric Publishing Textbook of Substance Abuse Treatment (4th ed.). United States of America: American Psychiatric Publishing Inc. p. 216. ISBN 978-1-58562-276-4.