CHEBI:50212 - pizotifen

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ChEBI Name pizotifen
ChEBI ID CHEBI:50212
Definition A benzocycloheptathiophene that is 9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene 4-ylidene)-1-methylpiperidine which is joined from the 4 position to the 4 position of an N-methylpiperidine moiety by a double bond. It is a sedating antihistamine, with strong serotonin antagonist and weak antimuscarinic activity. It is generally used as the malate salt for the treatment of migraine and the prevention of headache attacks during cluster periods.
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Formula C19H21NS
Net Charge 0
Average Mass 295.44278
Monoisotopic Mass 295.139
InChI InChI=1S/C19H21NS/c1-20-11-8-15(9-12-20)19-16-5-3-2-4-14(16)6-7-18-17(19)10-13-21-18/h2-5,10,13H,6-9,11-12H2,1H3
InChIKey FIADGNVRKBPQEU-UHFFFAOYSA-N
SMILES CN1CCC(CC1)=C1c2ccccc2CCc2sccc12
Roles Classification
Biological Role(s): serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
Application(s): serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
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ChEBI Ontology
Outgoing pizotifen (CHEBI:50212) has functional parent piperidine (CHEBI:18049)
pizotifen (CHEBI:50212) has role histamine antagonist (CHEBI:37956)
pizotifen (CHEBI:50212) has role muscarinic antagonist (CHEBI:48876)
pizotifen (CHEBI:50212) has role serotonergic antagonist (CHEBI:48279)
pizotifen (CHEBI:50212) is a benzocycloheptathiophene (CHEBI:50219)
pizotifen (CHEBI:50212) is conjugate base of pizotifen(1+) (CHEBI:50318)
Incoming pizotifen(1+) (CHEBI:50318) is conjugate acid of pizotifen (CHEBI:50212)
IUPAC Name
4-(9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)-1-methylpiperidine
INNs Sources
pizotifen KEGG DRUG
pizotifene ChemIDplus
pizotifeno ChemIDplus
pizotifenum ChemIDplus
Synonym Source
Pizotyline ChemIDplus
Database Links Databases
2220 DrugCentral
BE636717 Patent
D05523 KEGG DRUG
LSM-3695 LINCS
Pizotifen Wikipedia
US3272826 Patent
View more database links
Registry Numbers Types Sources
15574-96-6 CAS Registry Number ChemIDplus
753534 Reaxys Registry Number Reaxys
753534 Beilstein Registry Number Beilstein
Last Modified
22 February 2017