Clomipramine

Clomipramine

Clinical data
Trade names	Anafranil, Clofranil
AHFS/Drugs.com	Monograph
MedlinePlus	a697002
License data	US FDA: Clomipramine
Pregnancy category	AU: C US: C (Risk not ruled out)
Routes of administration	Oral, IV
ATC code	N06AA04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	50%
Protein binding	97-98%
Metabolism	Hepatic (CYP2D6-mediated)
Biological half-life	32 hr (69 hr for active metabolite)
Excretion	Renal (60%), faeces (32%)
Identifiers
IUPAC name 3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
CAS Number	303-49-1 Y
PubChem CID	2801
IUPHAR/BPS	2398
DrugBank	DB01242 Y
ChemSpider	2699 Y
UNII	NUV44L116D
KEGG	D07727 Y
ChEBI	CHEBI:47780 Y
ChEMBL	CHEMBL415 Y
ECHA InfoCard	100.005.587
Chemical and physical data
Formula	C19H23ClN2
Molar mass	314.9 g/mol
3D model (Jmol)	Interactive image
SMILES ClC1=CC(N(CCCN(C)C)C2=C(CC3)C=CC=C2)=C3C=C1
InChI InChI=1S/C19H23ClN2/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3 Y Key:GDLIGKIOYRNHDA-UHFFFAOYSA-N Y

Clomipramine, sold under the brand name Anafranil among others, is a tricyclic antidepressant (TCA). It is used for the treatment of obsessive compulsive disorder, panic disorder, major depressive disorder, and chronic pain. It may decrease the risk of suicide in those over the age of 65. It is taken by mouth.

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.

Clomipramine was discovered in 1964 by the Swiss drug manufacturer Ciba-Geigy. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale price in the developing world is between 0.11 and 0.21 per day as of 2014. In the United States a typical dose costs about 1.20 USD per day. It was made from imipramine.

Clomipramine has a number of uses in medicine including in the treatment of:

In a meta-analysis of various trials involving fluoxetine (Prozac), fluvoxamine (Luvox), and sertraline (Zoloft) to test their relative efficacies in treating OCD, clomipramine was found to be the most effective.