Clomipramine

Title: Clomipramine
CAS Registry Number: 303-49-1
CAS Name: 3-Chloro-10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine
Additional Names: 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine; 5-(g-dimethylaminopropyl)-3-chloroiminodibenzyl; chlorimipramine
Manufacturers' Codes: G-34586
Molecular Formula: C19H23ClN2
Molecular Weight: 314.85
Percent Composition: C 72.48%, H 7.36%, Cl 11.26%, N 8.90%
Literature References: Serotonin reuptake inhibitor. Prepn: P. N. Craig et al., J. Org. Chem. 26, 135 (1961); W. Schindler, H. Dietrich, CH 371799; eidem, US 3467650 (1963, 1969 both to Geigy). Crystal and molecular structure of the hydrochloride: M. L. Post, A. S. Horn, Acta Crystallogr. 33B, 2590 (1977). HPLC determn in serum: H. Weigmann et al., J. Chromatogr. B 710, 227 (1998). Veterinary trial in canine compulsive disorder: C. J. Hewson et al., J. Am. Vet. Med. Assoc. 213, 1760 (1998); in canine separation anxiety: S. Petit et al., Rev. Med. Vet. 150, 133 (1999). Review of pharmacology and clinical experience in obsessive-compulsive disorder and depression: M. D. Peters et al., Clin. Pharm. 9, 165-178 (1990).
Properties: bp0.3 160-170°.
Boiling point: bp0.3 160-170°
Derivative Type: Hydrochloride
CAS Registry Number: 17321-77-6
Trademarks: Anafranil (Novartis); Clomicalm (Novartis)
Molecular Formula: C19H23ClN2.HCl
Molecular Weight: 351.31
Percent Composition: C 64.96%, H 6.89%, Cl 20.18%, N 7.97%
Properties: Crystals from acetone-ether/methanol-ether, mp 189-190° (Craig); also reported as crystals from acetone, mp 191.5-192° (Schindler, Dietrich). Freely sol in water, methanol, methylene chloride. Practically insol in ethyl ether, hexane.
Melting point: mp 189-190° (Craig); mp 191.5-192° (Schindler, Dietrich)
Therap-Cat: Antidepressant; antiobsessional agent.
Therap-Cat-Vet: In treatment of canine separation anxiety.
Keywords: Antidepressant; Tricyclics; Antiobsessional.
Clomocycline Clonazepam Clonidine Clonitazene Clonitrate

Clomipramine
Clomipramine2DACS.svg
Clomipramine3DanBS.gif
Systematic (IUPAC) name
3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
Clinical data
Trade names Anafranil
AHFS/Drugs.com monograph
MedlinePlus a697002
Licence data US FDA:link
Pregnancy cat. C (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral, IV[1]
Pharmacokinetic data
Bioavailability 50%
Protein binding 97-98%
Metabolism Hepatic (CYP2D6-mediated)
Half-life 32 hr (69 hr for active metabolite)
Excretion Renal (60%), faeces (32%)
Identifiers
CAS number 303-49-1 YesY
ATC code N06AA04
PubChem CID 2801
IUPHAR ligand 2398
DrugBank DB01242
ChemSpider 2699 YesY
UNII NUV44L116D YesY
KEGG D07727 YesY
ChEBI CHEBI:47780 YesY
ChEMBL CHEMBL415 YesY
Chemical data
Formula C19H23ClN2 
Mol. mass 314.9 g/mol
 YesY (what is this?)  (verify)

Clomipramine (trademarked as Anafranil) is a tricyclic antidepressant (TCA). It was developed in the early 1960s[2] by the Swiss drug manufacturer Geigy (now known as Novartis) and has been in clinical use worldwide ever since. It is the 3-chlorinated derivative of the earlier tricyclic, imipramine.