granisetron (CHEBI:5537)

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ChEBI Name	granisetron

ChEBI ID	CHEBI:5537

Definition	A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1H-indazole-3-carboxylic acid with the primary amino group of (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A selective 5-HT₃ receptor antagonist, it is used (generally as the monohydrochloride salt) to manage nausea and vomiting caused by cancer chemotherapy and radiotherapy, and to prevent and treat postoperative nausea and vomiting.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C18H24N4O

Net Charge

Average Mass

312.40940

Monoisotopic Mass

312.19501

InChI

InChI=1S/C18H24N4O/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23)/t12-,13+,14-

InChIKey

MFWNKCLOYSRHCJ-BTTYYORXSA-N

SMILES

CN1[C@H]2CCC[C@@H]1C[C@@H](C2)NC(=O)c1nn(C)c2ccccc12

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):	serotonergic antagonist Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.

Application(s):	serotonergic antagonist Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists. antiemetic A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.

ChEBI Ontology
Outgoing	granisetron (CHEBI:5537) has role antiemetic (CHEBI:50919) granisetron (CHEBI:5537) has role serotonergic antagonist (CHEBI:48279) granisetron (CHEBI:5537) is a indazoles (CHEBI:38769) granisetron (CHEBI:5537) is a monocarboxylic acid amide (CHEBI:29347) granisetron (CHEBI:5537) is a tertiary amino compound (CHEBI:50996)

IUPAC Name

1-methyl-N-[(3-endo)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide

Synonyms	Sources
1-methyl-N-(9-methyl-endo-9-azabicyclo(3.3.1)non-3-yl)-1H-indazole-3-carboxamide	ChemIDplus
APF 530	ChemIDplus
APF530	ChemIDplus
BRL 43694	ChemIDplus

Last Modified

23 February 2017