Structure via PubChem · Public domain (PubChem)
clomipramine
Sign in to saveAlso known as 3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine, 3-chloroimipramine, chlorimipramine, monochlorimipramine, 3-(3-chloro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
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 hyperacusis, panic disorder, major depressive disorder, trichotillomania, body dysmorphic disorder and chronic pain. It has also been notably used to treat premature ejaculation and the cataplexy associated with narcolepsy.
OverviewAI-generated
Clomipramine is a chemical compound with the formula C₁₉H₂₃ClN₂. Its IUPAC name is 3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine. The molecule has a mass of 314.155 and a weight of 314.9. It features a charge of 0, two hydrogen bond acceptors, and no hydrogen bond donors. The compound's xlogp value is 5.2, and its topological polar surface area is 6.5.
The stylized name for the substance is clomiPRAMINE. It is associated with a Commons category titled "Clomipramine." In scientific literature, there are 4256 PubMed entries related to clomipramine. Additionally, the subject is referenced by 2,844 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 459591021
- Drug.image
- Clomipramine2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.alt
- Skeletal formula of clomipramine
- Drug.width
- 200
- Drug.image2
- Clomipramine-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of the clomipramine molecule
- Drug.width2
- 200
- Drug.tradename
- Anafranil, Clomicalm, others
- Drug.MedlinePlus
- a697002
- Drug.DailyMedID
- Clomipramine
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth, intravenous
- Drug.ATC_prefix
- N06
- Drug.ATC_suffix
- AA04
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C19H23ClN2
- Molecular weight
- 314.9 g/mol
- IUPAC name
- 3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine
- SMILES
- CN(C)CCCN1C2=CC=CC=C2CCC3=C1C=C(C=C3)Cl
- InChIKey
- GDLIGKIOYRNHDA-UHFFFAOYSA-N
- XLogP
- 5.2
- Polar surface area
- 6.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
4,256 papers- Clomipramine: an antiobsessive drug.Canadian journal of psychiatry. Revue canadienne de psychiatrie · 1986
- Clomipramine for obsessive-compulsive disorder.American family physician · 1991
- Clinical pharmacokinetics of clomipramine.Clinical pharmacokinetics · 1991
- Clomipramine-induced pancytopenia.The Journal of nervous and mental disease · 1987
- Clomipramine: an antiobsessional tricyclic antidepressant.Clinical pharmacy · 1990
via PubMed
Wikidata facts
- Mass
- 314.155
- Has use
- medication
Show 9 more facts
- chemical formula
- C₁₉H₂₃ClN₂
- significant drug interaction
- enalapril
- Commons category
- Clomipramine
- canonical SMILES
- CN(C)CCCN1C2=CC=CC=C2CCC3=C1C=C(C=C3)Cl
- World Health Organisation international non-proprietary name
- clomipramine
- medical condition treated
- obsessive-compulsive disorder
- subject has role
- essential medicine
- physically interacts with
- solute carrier family 6 member 4
- stylized name
- clomiPRAMINE
Sources (9)
via Wikidata · CC0
~33 min read
Encyclopedic overview
19 sectionsContents
- Medical uses
- Contraindications
- Pregnancy and lactation
- Side effects
- Withdrawal
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Serotonergic activity
- Obsessive–compulsive disorder
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Veterinary uses
- References
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 hyperacusis, panic disorder, major depressive disorder, trichotillomania, body dysmorphic disorder and chronic pain. It has also been notably used to treat premature ejaculation and the cataplexy associated with narcolepsy.
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.
Excerpted from Wikipedia’s “clomipramine” article, available under the CC BY-SA 4.0 licence.