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Antidepressant From Wikipedia, the free encyclopedia
Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used in the treatment of depression.[8] It acts as a relatively selective norepinephrine reuptake inhibitor, though it does also have other activities such as weak serotonin reuptake inhibitory, α1-blocking, antihistamine, and anticholinergic effects. The drug is not considered a first-line treatment for depression since the introduction of selective serotonin reuptake inhibitor (SSRI) antidepressants, which have fewer side effects and are safer in overdose.
Clinical data | |
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Trade names | Norpramin, Pertofrane, others |
Other names | Desmethylimipramine; Norimipramine; EX-4355; G-35020; JB-8181; NSC-114901[1][2][3] |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682387 |
Routes of administration | Oral, intramuscular injection |
ATC code | |
Legal status | |
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Pharmacokinetic data | |
Bioavailability | 60–70%[6] |
Protein binding | 91%[6] |
Metabolism | Liver (CYP2D6)[7] |
Elimination half-life | 12–30 hours[6] |
Excretion | Urine (70%), feces[6] |
Identifiers | |
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IUPHAR/BPS | |
DrugBank | |
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ChEBI | |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.037 |
Chemical and physical data | |
Formula | C18H22N2 |
Molar mass | 266.388 g·mol−1 |
3D model (JSmol) | |
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Desipramine is primarily used for the treatment of depression.[8] It may also be useful to treat symptoms of attention-deficit hyperactivity disorder (ADHD).[9] Evidence of benefit is only in the short term, and with concerns of side effects its overall usefulness is not clear.[10] Desipramine at very low doses is also used to help reduce the pain associated with functional dyspepsia.[11] It has also been tried, albeit with little evidence of effectiveness, in the treatment of cocaine dependence.[12] Evidence for usefulness in neuropathic pain is also poor.[13]
Desipramine tends to be less sedating than other TCAs and tends to produce fewer anticholinergic effects such as dry mouth, constipation, urinary retention, blurred vision, and cognitive or memory impairments.[14]
Desipramine is particularly toxic in cases of overdose, compared to other antidepressants.[15] Any overdose or suspected overdose of desipramine is considered to be a medical emergency and can result in death without prompt medical intervention.
Site | Ki (nM) | Species | Ref |
---|---|---|---|
SERT | 17.6–163 | Human | [17][18] |
NET | 0.63–3.5 | Human | [17][18] |
DAT | 3,190 | Human | [17] |
5-HT1A | ≥6,400 | Human | [19][20] |
5-HT2A | 115–350 | Human | [19][20] |
5-HT2C | 244–748 | Rat | [21][22] |
5-HT3 | ≥2,500 | Rodent | [22][23] |
5-HT7 | >1,000 | Rat | [24] |
α1 | 23–130 | Human | [19][25][18] |
α2 | ≥1,379 | Human | [19][25][18] |
β | ≥1,700 | Rat | [26][27] |
Cav2.2 | 410 | Human | [28] |
D1 | 5,460 | Human | [29] |
D2 | 3,400 | Human | [19][25] |
H1 | 60–110 | Human | [19][25][30] |
H2 | 1,550 | Human | [30] |
H3 | >100,000 | Human | [30] |
H4 | 9,550 | Human | [30] |
mACh | 66–198 | Human | [19][25] |
M1 | 110 | Human | [31] |
M2 | 540 | Human | [31] |
M3 | 210 | Human | [31] |
M4 | 160 | Human | [31] |
M5 | 143 | Human | [31] |
σ1 | 1,990–4,000 | Rodent | [32][33] |
σ2 | ≥1,611 | Rat | [16][33] |
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site. |
Desipramine is a very potent and relatively selective norepinephrine reuptake inhibitor (NRI), which is thought to enhance noradrenergic neurotransmission.[34][35] Based on one study, it has the highest affinity for the norepinephrine transporter (NET) of any other TCA,[17] and is said to be the most noradrenergic[36] and the most selective for the NET of the TCAs.[34] The observed effectiveness of desipramine in the treatment of ADHD was the basis for the development of the selective NRI atomoxetine and its use in ADHD.[34]
Desipramine has the weakest antihistamine and anticholinergic effects of the TCAs.[37][36][38] It tends to be slightly activating/stimulating rather than sedating, unlike most others TCAs.[36] Whereas other TCAs are useful for treating insomnia, desipramine can cause insomnia as a side effect due to its activating properties.[36] The drug is also not associated with weight gain, in contrast to many other TCAs.[36] Secondary amine TCAs like desipramine and nortriptyline have a lower risk of orthostatic hypotension than other TCAs,[39][40] although desipramine can still cause moderate orthostatic hypotension.[41]
Desipramine is the major metabolite of imipramine and lofepramine.[42]
Desipramine is a tricyclic compound, specifically a dibenzazepine, and possesses three rings fused together with a side chain attached in its chemical structure.[43] Other dibenzazepine TCAs include imipramine (N-methyldesipramine), clomipramine, trimipramine, and lofepramine (N-(4-chlorobenzoylmethyl)desipramine).[43][44] Desipramine is a secondary amine TCA, with its N-methylated parent imipramine being a tertiary amine.[45][46] Other secondary amine TCAs include nortriptyline and protriptyline.[47][48] The chemical name of desipramine is 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine and its free base form has a chemical formula of C18H22N2 with a molecular weight of 266.381 g/mol.[1] The drug is used commercially mostly as the hydrochloride salt; the dibudinate salt is or has been used for intramuscular injection in Argentina (brand name Nebril) and the free base form is not used.[1][2] The CAS Registry Number of the free base is 50-47-5, of the hydrochloride is 58-28-6, and of the dibudinate is 62265-06-9.[1][2][49]
Desipramine was developed by Geigy.[50] It first appeared in the literature in 1959 and was patented in 1962.[50] The drug was first introduced for the treatment of depression in 1963 or 1964.[50][51]
Desipramine is the generic name of the drug and its INN and BAN , while desipramine hydrochloride is its USAN , USP , BAN , and JAN .[1][2][52][3] Its generic name in French and its DCF are désipramine, in Spanish and Italian and its DCIT are desipramina, in German is desipramin, and in Latin is desipraminum.[2][3]
Desipramine is or has been marketed throughout the world under a variety of brand names, including Irene, Nebril, Norpramin, Pertofran, Pertofrane, Pertrofran, and Petylyl among others.[2][3]
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