MedPath

Clomipramine

Generic Name
Clomipramine
Brand Names
Anafranil
Drug Type
Small Molecule
Chemical Formula
C19H23ClN2
CAS Number
303-49-1
Unique Ingredient Identifier
NUV44L116D

Overview

Clomipramine, the 3-chloro analog of imipramine, is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, clomipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, clomipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as clomipramine, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H receptors, α-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Clomipramine may be used to treat obsessive-compulsive disorder and disorders with an obsessive-compulsive component (e.g. depression, schizophrenia, Tourette’s disorder). Unlabeled indications include panic disorder, chronic pain (e.g. central pain, idiopathic pain disorder, tension headache, diabetic peripheral neuropathy, neuropathic pain), cataplexy and associated narcolepsy, autistic disorder, trichotillomania, onchophagia, stuttering, premature ejaculation, and premenstrual syndrome. Clomipramine is rapidly absorbed from the gastrointestinal tract and demethylated in the liver to its primary active metabolite, desmethylclomipramine.

Background

Clomipramine, the 3-chloro analog of imipramine, is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, clomipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, clomipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as clomipramine, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H receptors, α-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Clomipramine may be used to treat obsessive-compulsive disorder and disorders with an obsessive-compulsive component (e.g. depression, schizophrenia, Tourette’s disorder). Unlabeled indications include panic disorder, chronic pain (e.g. central pain, idiopathic pain disorder, tension headache, diabetic peripheral neuropathy, neuropathic pain), cataplexy and associated narcolepsy, autistic disorder, trichotillomania, onchophagia, stuttering, premature ejaculation, and premenstrual syndrome. Clomipramine is rapidly absorbed from the gastrointestinal tract and demethylated in the liver to its primary active metabolite, desmethylclomipramine.

Indication

May be used to treat obsessive-compulsive disorder and disorders with an obsessive-compulsive component (e.g. depression, schizophrenia, Tourette’s disorder). Unlabeled indications include: depression, panic disorder, chronic pain (e.g. central pain, idiopathic pain disorder, tension headache, diabetic peripheral neuropathy, neuropathic pain), cataplexy and associated narcolepsy (limited evidence), autistic disorder (limited evidence), trichotillomania (limited evidence), onchophagia (limited evidence), stuttering (limited evidence), premature ejaculation, and premenstrual syndrome.

Associated Conditions

  • Depression
  • Obsessive Compulsive Disorder (OCD)
  • Panic Disorder

FDA Approved Products

CLOMIPRAMINE HYDROCHLORIDE
Manufacturer:Alembic Pharmaceuticals Limited
Route:ORAL
Strength:75 mg in 1 1
Approved: 2023/01/27
NDC:46708-409
CLOMIPRAMINE HYDROCHLORIDE
Manufacturer:Alembic Pharmaceuticals Limited
Route:ORAL
Strength:50 mg in 1 1
Approved: 2023/01/27
NDC:46708-408
CLOMIPRAMINE HYDROCHLORIDE
Manufacturer:Golden State Medical Supply, Inc.
Route:ORAL
Strength:75 mg in 1 1
Approved: 2023/04/25
NDC:51407-759
Clomipramine Hydrochloride
Manufacturer:Aurobindo Pharma Limited
Route:ORAL
Strength:75 mg in 1 1
Approved: 2023/03/20
NDC:59651-383
Clomipramine Hydrochloride
Manufacturer:Upsher-Smith Laboratories, LLC
Route:ORAL
Strength:75 mg in 1 1
Approved: 2019/11/29
NDC:0832-0632

Singapore Approved Products

APO-CLOMIPRAMINE TABLET 25 mg
Manufacturer:APOTEX INC
Form:TABLET, FILM COATED
Strength:25 mg
Online:Yes
Approved: 1996/11/28
Approval:SIN09018P
APO-CLOMIPRAMINE TABLET 10 mg
Manufacturer:APOTEX INC
Form:TABLET, FILM COATED
Strength:10 mg
Online:Yes
Approved: 1996/12/09
Approval:SIN09058P
DEPRANIL TABLET 25 mg
Manufacturer:DUOPHARMA (M) SDN BHD
Form:TABLET
Strength:25 mg
Online:Yes
Approved: 1998/01/26
Approval:SIN09611P

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