Clomipramine
Clomipramine, sold under the brand name Anafranil among others, is a tricyclic antidepressant (TCA). It is used in the treatment of various conditions, most-notably obsessive–compulsive disorder but also many other disorders, including panic disorder, major depressive disorder, trichotilomania, body dysmorphic disorder and chronic pain. It has also been notably used to treat premature ejaculation and the cataplexy associated with narcolepsy.
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| Trade names | Anafranil, Clomicalm, others |
| Other names | Clomipramine; 3-Chloroimipramine; G-34586 |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a697002 |
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| Routes of administration | By mouth, intravenous |
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| Bioavailability | ~50% |
| Protein binding | 96–98% |
| Metabolism | Hepatic (CYP2D6) |
| Metabolites | Desmethylclomipramine |
| Elimination half-life | CMI: 19–37 hours DCMI: 54–77 hours |
| Excretion | Renal (51–60%) Feces (24–32%) |
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| ECHA InfoCard | 100.005.587 |
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| Formula | C19H23ClN2 |
| Molar mass | 314.86 g·mol−1 |
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It may also address certain fundamental features surrounding narcolepsy besides cataplexy (especially hypnagogic and hypnopompic hallucinations). The evidence behind this, however, is less robust.
As with other antidepressants (notably including selective serotonin reuptake inhibitors), it may paradoxically increase the risk of suicide in those under the age of 25, at least in the first few weeks of treatment.
It is typically taken by mouth, although intravenous preparations are sometimes used.
Common side effects include dry mouth, constipation, loss of appetite, sleepiness, weight gain, sexual dysfunction, and trouble urinating. Serious side effects include an increased risk of suicidal behavior in those under the age of 25, seizures, mania, and liver problems. If stopped suddenly, a withdrawal syndrome may occur with headaches, sweating, and dizziness. It is unclear if it is safe for use in pregnancy. Its mechanism of action is not entirely clear but is believed to involve increased levels of serotonin and norepinephrine.
Clomipramine was discovered in 1964 by the Swiss drug manufacturer Ciba-Geigy. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.