CHEBI:4046 - cyproheptadine

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ChEBI Name cyproheptadine
ChEBI ID CHEBI:4046
Definition The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzo[a,d]cycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:111005, CHEBI:605605
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Formula C21H21N
Net Charge 0
Average Mass 287.39810
Monoisotopic Mass 287.167
InChI InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3
InChIKey JJCFRYNCJDLXIK-UHFFFAOYSA-N
SMILES CN1CCC(CC1)=C1c2ccccc2C=Cc2ccccc12
Roles Classification
Biological Role(s): H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
Application(s): H1-receptor antagonist
H1-receptor antagonists are the drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
anti-allergic agent
A drug used to treat allergic reactions.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cyproheptadine (CHEBI:4046) has role anti-allergic agent (CHEBI:50857)
cyproheptadine (CHEBI:4046) has role antipruritic drug (CHEBI:59683)
cyproheptadine (CHEBI:4046) has role gastrointestinal drug (CHEBI:55324)
cyproheptadine (CHEBI:4046) has role H1-receptor antagonist (CHEBI:37955)
cyproheptadine (CHEBI:4046) has role serotonergic antagonist (CHEBI:48279)
cyproheptadine (CHEBI:4046) is a piperidines (CHEBI:26151)
cyproheptadine (CHEBI:4046) is a tertiary amine (CHEBI:32876)
Incoming cyproheptadine hydrochloride (anhydrous) (CHEBI:59695) has part cyproheptadine (CHEBI:4046)
IUPAC Names
4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine
4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine
INNs Sources
ciproheptadina ChemIDplus
cyproheptadine ChemIDplus
cyproheptadinum ChemIDplus
Synonyms Sources
1-methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidine ChemIDplus
1-Methyl-4-(5H-dibenzo(a,d)cycloheptenylidene)piperidine ChemIDplus
4-(5-dibenzo(a,d)cyclohepten-5-ylidine)-1-methylpiperidine ChemIDplus
4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-methylpiperidine ChemIDplus
4-Dibenzo[a,d]cyclohepten-5-ylidene-1-methyl-piperidine ChEMBL
5-(1-methylpiperidylidene-4)-5H-dibenzo(a,d)cyclopheptene ChemIDplus
cyproheptadine ChEMBL
CYPROHEPTADINE ChEMBL
Cyproheptadine KEGG COMPOUND
Database Links Databases
765 DrugCentral
C06935 KEGG COMPOUND
Cyproheptadine Wikipedia
D07765 KEGG DRUG
DB00434 DrugBank
LSM-5419 LINCS
US3014911 Patent
View more database links
Registry Numbers Types Sources
129-03-3 CAS Registry Number KEGG COMPOUND
129-03-3 CAS Registry Number ChemIDplus
129-03-3 CAS Registry Number NIST Chemistry WebBook
1348386 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
10843226 PubMed citation ChEMBL
Last Modified
22 February 2017