CHEBI:47780 - clomipramine

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ChEBI Name clomipramine
ChEBI ID CHEBI:47780
Definition A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine which is substituted by chlorine at position 3 and in which the hydrogen attached to the nitrogen is replaced by a 3-(dimethylamino)propyl group. One of the more sedating tricyclic antidepressants, it is used as the hydrochloride salt for the treatment of depression as well as obsessive-compulsive disorder and phobias.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:47359, CHEBI:3754
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Formula C19H23ClN2
Net Charge 0
Average Mass 314.85210
Monoisotopic Mass 314.155
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
InChIKey GDLIGKIOYRNHDA-UHFFFAOYSA-N
SMILES CN(C)CCCN1c2ccccc2CCc2ccc(Cl)cc12
Roles Classification
Biological Role(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
serotonergic drug

EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of trypanothione-disulfide reductase (EC 1.8.1.12).
Application(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
serotonergic drug

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ChEBI Ontology
Outgoing clomipramine (CHEBI:47780) has functional parent imipramine (CHEBI:47499)
clomipramine (CHEBI:47780) has role antidepressant (CHEBI:35469)
clomipramine (CHEBI:47780) has role EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor (CHEBI:77402)
clomipramine (CHEBI:47780) has role serotonergic antagonist (CHEBI:48279)
clomipramine (CHEBI:47780) has role serotonergic drug (CHEBI:48278)
clomipramine (CHEBI:47780) has role serotonin uptake inhibitor (CHEBI:50949)
clomipramine (CHEBI:47780) is a dibenzoazepine (CHEBI:47804)
clomipramine (CHEBI:47780) is conjugate base of clomipramine(1+) (CHEBI:64209)
Incoming clomipramine(1+) (CHEBI:64209) is conjugate acid of clomipramine (CHEBI:47780)
IUPAC Name
3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine
Synonyms Sources
3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine NIST Chemistry WebBook
3-(3-CHLORO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N,N-DIMETHYLPROPAN-1-AMINE PDBeChem
3-chloroimipramine ChemIDplus
chlorimipramine NIST Chemistry WebBook
Clomipramine KEGG COMPOUND
G 34586 NIST Chemistry WebBook
monochlorimipramine NIST Chemistry WebBook
Database Links Databases
701 DrugCentral
C06918 KEGG COMPOUND
CH371799 Patent
Clomipramine Wikipedia
CXX PDBeChem
D07727 KEGG DRUG
DB01242 DrugBank
LSM-3171 LINCS
US3467650 Patent
View more database links
Registry Numbers Types Sources
1323477 Reaxys Registry Number Reaxys
1323477 Beilstein Registry Number ChemIDplus
303-49-1 CAS Registry Number KEGG COMPOUND
303-49-1 CAS Registry Number ChemIDplus
303-49-1 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
12007764 PubMed citation Europe PMC
12084414 PubMed citation Europe PMC
16085036 PubMed citation Europe PMC
17471183 PubMed citation Europe PMC
19747949 PubMed citation Europe PMC
19810911 PubMed citation Europe PMC
Last Modified
22 February 2017