CHEBI:73274 - canagliflozin

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ChEBI Name canagliflozin
ChEBI ID CHEBI:73274
Definition A C-glycosyl compound that is used (in its hemihydrate form) for treatment of type II diabetes via inhibition of sodium-glucose transport protein subtype 2.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H25FO5S
Net Charge 0
Average Mass 444.518
Monoisotopic Mass 444.141
InChI InChI=1S/C24H25FO5S/c1-13-2-3-15(24-23(29)22(28)21(27)19(12-26)30-24)10-16(13)11-18-8-9-20(31-18)14-4-6-17(25)7-5-14/h2-10,19,21-24,26-29H,11-12H2,1H3/t19-,21-,22+,23-,24+/m1/s1
InChIKey XTNGUQKDFGDXSJ-ZXGKGEBGSA-N
SMILES [C@@H]1([C@@H]([C@H]([C@@](O[C@@H]1CO)(C2=CC=C(C(=C2)CC=3SC(=CC3)C4=CC=C(C=C4)F)C)[H])O)O)O
Roles Classification
Biological Role(s): sodium-glucose transport protein subtype 2 inhibitor
An inhibitor that interferes with the action of sodium-glucose transport protein subtype 2.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing canagliflozin (CHEBI:73274) has role hypoglycemic agent (CHEBI:35526)
canagliflozin (CHEBI:73274) has role sodium-glucose transport protein subtype 2 inhibitor (CHEBI:73273)
canagliflozin (CHEBI:73274) is a C-glycosyl compound (CHEBI:20857)
canagliflozin (CHEBI:73274) is a organofluorine compound (CHEBI:37143)
canagliflozin (CHEBI:73274) is a thiophenes (CHEBI:26961)
Incoming canagliflozin hydrate (CHEBI:73272) has part canagliflozin (CHEBI:73274)
IUPAC Name
(1S)-1,5-anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol
Synonym Source
1-(Glucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thienylmethyl)benzene ChemIDplus
Manual Xrefs Databases
4758 DrugCentral
Canagliflozin Wikipedia
US2008146515 Patent
US2010099883 Patent
US2012289694 Patent
WO2009035969 Patent
WO2011142478 Patent
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Registry Numbers Types Sources
18362681 Reaxys Registry Number Reaxys
842133-18-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017