Clomipramine hydrochlorideProduct ingredient for Clomipramine
- Name
- Clomipramine hydrochloride
- Drug Entry
- Clomipramine
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-H1 receptors, α1-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.
- Accession Number
- DBSALT000028
- Structure
- Synonyms
- Clomipramine HCl
- External IDs
- G 34586 / G-34586
- UNII
- 2LXW0L6GWJ
- CAS Number
- 17321-77-6
- Weight
- Average: 351.313
Monoisotopic: 350.131654192 - Chemical Formula
- C19H24Cl2N2
- InChI Key
- WIMWMKZEIBHDTH-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H23ClN2.ClH/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;1H
- IUPAC Name
- (3-{14-chloro-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylamine hydrochloride
- SMILES
- Cl.CN(C)CCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2
- External Links
- PubChem Compound
- 68539
- ChemSpider
- 61813
- ChEBI
- 3755
- ChEMBL
- CHEMBL1200710
- Wikipedia
- Clomipramine
- Predicted Properties
Property Value Source Water Solubility 0.0144 mg/mL ALOGPS logP 5.04 ALOGPS logP 4.88 Chemaxon logS -4.3 ALOGPS pKa (Strongest Basic) 9.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 95.41 m3·mol-1 Chemaxon Polarizability 36.15 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon