Mexazolam

Mexazolam^[1] (marketed under the trade names Melex and Sedoxil)^[2] is a drug which is a benzodiazepine derivative.^[3] Mexazolam has been trialed for anxiety and was found to be effective in alleviating anxiety at one week follow-up. Mexazolam is metabolised via the CYP3A4 pathway. HMG-CoA reductase inhibitors including simvastatin, simvastatin acid, lovastatin, fluvastatin, atorvastatin and cerivastatin inhibit the metabolism of mexazolam,^[4] but not the HMG-CoA reductase inhibitor pravastatin.^[5][6] Its principal active metabolites are chlorodesmethyldiazepam (also known as chloronordiazepam or delorazepam, trade name Dadumir) and chloroxazepam (also known as lorazepam, trade name Ativan).^[7]

Mexazolam

Clinical data
Trade names	Melex, Sedoxil
Other names	13-chloro- 2-(2-chlorophenyl)- 5-methyl- 3-oxa- 6,9-diazatricyclo[8.4.0.02,6] tetradeca- 1(10),11,13-trien- 8-one
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N05BA25 (WHO)
Legal status
Legal status	CA: Schedule IV
Pharmacokinetic data
Metabolism	Liver (CYP3A4)
Excretion	Kidney
Identifiers
IUPAC name 10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one
CAS Number	31868-18-5
PubChem CID	4177
ChemSpider	4033 Y
UNII	S5969B6237
KEGG	D01316 Y
CompTox Dashboard (EPA)	DTXSID9057715
Chemical and physical data
Formula	C18H16Cl2N2O2
Molar mass	363.24 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc1ccccc1C42OCC(N2CC(=O)Nc3c4cc(Cl)cc3)C
InChI InChI=1S/C18H16Cl2N2O2/c1-11-10-24-18(13-4-2-3-5-15(13)20)14-8-12(19)6-7-16(14)21-17(23)9-22(11)18/h2-8,11H,9-10H2,1H3,(H,21,23) Y Key:ANUCDXCTICZJRH-UHFFFAOYSA-N Y
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See also

• Benzodiazepine
• Delorazepam
• Lorazepam

References

1. DE Patent 1954065
2. "Benzodiazepine Names". non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2009-04-05.
3. Kurono Y, Kamiya K, Kuwayama T, Jinno Y, Yashiro T, Ikeda K (September 1987). "Kinetics and mechanism of the acid-base equilibrium of mexazolam and comparison with those of other commercial benzodiazepinooxazole drugs". Chemical & Pharmaceutical Bulletin. 35 (9): 3831–3837. doi:10.1248/cpb.35.3831. PMID 2893667.
4. Mc Donnell CG, Harte S, O'Driscoll J, O'Loughlin C, Van Pelt FN, Shorten GD (September 2003). "The effects of concurrent atorvastatin therapy on the pharmacokinetics of intravenous midazolam". Anaesthesia. 58 (9): 899–904. doi:10.1046/j.1365-2044.2003.03339.x. PMID 12911366. S2CID 25382546.
5. Ishigami M, Takasaki W, Ikeda T, Komai T, Ito K, Sugiyama Y (August 2002). "Sex difference in inhibition of in vitro mexazolam metabolism by various 3-hydroxy-3-methylglutaryl-coenzyme a reductase inhibitors in rat liver microsomes". Drug Metabolism and Disposition. 30 (8): 904–910. doi:10.1124/dmd.30.8.904. PMID 12124308. S2CID 2620104.
6. Ishigami M, Honda T, Takasaki W, Ikeda T, Komai T, Ito K, Sugiyama Y (March 2001). "A comparison of the effects of 3-hydroxy-3-methylglutaryl-coenzyme a (HMG-CoA) reductase inhibitors on the CYP3A4-dependent oxidation of mexazolam in vitro". Drug Metabolism and Disposition. 29 (3): 282–288. PMID 11181496.
7. Fernandes H, Moreira R (June 2014). "Mexazolam: clinical efficacy and tolerability in the treatment of anxiety". Neurology and Therapy. 3 (1): 1–14. doi:10.1007/s40120-014-0016-7. PMC 4381915. PMID 26000220.