CHEBI:71272 - saxagliptin

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ChEBI Name saxagliptin
ChEBI ID CHEBI:71272
Definition A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-amino(3-hydroxyadamantan-1-yl)acetic acid with the amino group of (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile. Used in its monohydrate form for the treatment of Type II diabetes.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H25N3O2
Net Charge 0
Average Mass 315.41000
Monoisotopic Mass 315.195
InChI InChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10?,11?,12-,13+,14+,15-,17?,18?/m1/s1
InChIKey QGJUIPDUBHWZPV-SGTAVMJGSA-N
SMILES [H][C@]12C[C@@H](C#N)N(C(=O)[C@@H](N)C34CC5CC(CC(O)(C5)C3)C4)[C@@]1([H])C2
Roles Classification
Biological Role(s): EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor
An EC 3.4.14.* (dipeptidyl- and tripeptidyl-peptidases) inhibitor that specifically inhibits dipeptidyl peptidase-4 (EC 3.4.14.5).
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing saxagliptin (CHEBI:71272) has role EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor (CHEBI:68612)
saxagliptin (CHEBI:71272) has role hypoglycemic agent (CHEBI:35526)
saxagliptin (CHEBI:71272) is a adamantanes (CHEBI:51339)
saxagliptin (CHEBI:71272) is a azabicycloalkane (CHEBI:38295)
saxagliptin (CHEBI:71272) is a monocarboxylic acid amide (CHEBI:29347)
saxagliptin (CHEBI:71272) is a nitrile (CHEBI:18379)
saxagliptin (CHEBI:71272) is a tertiary alcohol (CHEBI:26878)
Incoming saxagliptin hydrate (CHEBI:71271) has part saxagliptin (CHEBI:71272)
IUPAC Name
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
INN Source
saxagliptin KEGG DRUG
Synonyms Sources
(1S,3S,5S)-2-((2S)-Amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile ChemIDplus
BMS 477118 ChemIDplus
BMS-477118 DrugBank
Database Links Databases
D08996 KEGG DRUG
DB06335 DrugBank
HMDB15634 HMDB
Saxagliptin Wikipedia
US2005222242 Patent
US2007172525 Patent
WO2007078726 Patent
WO2009022009 Patent
WO2011125011 Patent
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Registry Numbers Types Sources
10201614 Reaxys Registry Number Reaxys
361442-04-8 CAS Registry Number ChemIDplus
361442-04-8 CAS Registry Number KEGG DRUG
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Last Modified
06 March 2014