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CHEBI:4046 - cyproheptadine

Default Structure
ChEBI IDCHEBI:4046
ChEBI Namecyproheptadine
Stars
DefinitionThe 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.
Secondary ChEBI IDsCHEBI:111005, CHEBI:605605
Last Modified22 February 2017
DownloadsMolfile
FormulaC21H21N
Net Charge0
Average Mass287.406
Monoisotopic Mass287.16740
SMILESCN1CCC(=C2c3ccccc3C=Cc3ccccc32)CC1
InChIInChI=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
InChIKeyJJCFRYNCJDLXIK-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
Applications:
anti-allergic agent  A drug used to treat allergic reactions.
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.
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.
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).
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
ciproheptadinaChemIDplus
cyproheptadineChemIDplus
cyproheptadinumChemIDplus
Synonyms  Source
1-methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidineChemIDplus
1-Methyl-4-(5H-dibenzo(a,d)cycloheptenylidene)piperidineChemIDplus
4-(5-dibenzo(a,d)cyclohepten-5-ylidine)-1-methylpiperidineChemIDplus
4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-methylpiperidineChemIDplus
4-Dibenzo[a,d]cyclohepten-5-ylidene-1-methyl-piperidineChEMBL
5-(1-methylpiperidylidene-4)-5H-dibenzo(a,d)cyclophepteneChemIDplus
Manual XrefsDatabases
765DrugCentral
C06935KEGG COMPOUND
CyproheptadineWikipedia
D07765KEGG DRUG
DB00434DrugBank
LSM-5419LINCS
US3014911Patent
Registry NumbersSources
Beilstein:1348386Beilstein
CAS:129-03-3NIST Chemistry WebBook
CAS:129-03-3KEGG COMPOUND
CAS:129-03-3ChemIDplus
Citations