cyproheptadine (CHEBI:4046)

ChEBI > Main

Main

ChEBI Ontology

Automatic Xrefs

Reactions

Pathways

Models

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

Supplier Information

Download	Molfile XML SDF

Wikipedia	License

Read full article at Wikipedia

Formula

C21H21N

Net Charge

Average Mass

287.39810

Monoisotopic Mass

287.16740

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
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

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.

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

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

Citation	Type	Source
10843226	PubMed citation	ChEMBL

Last Modified

22 February 2017