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CHEBI:40237 - sitagliptin

ChEBI IDCHEBI:40237
ChEBI Namesitagliptin
Stars
DefinitionA triazolopyrazine that exhibits hypoglycemic activity.
Last Modified22 February 2017
DownloadsMolfile
FormulaC16H15F6N5O
Net Charge0
Average Mass407.318
Monoisotopic Mass407.11808
SMILESN[C@@H](CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F
InChIInChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1
InChIKeyMFFMDFFZMYYVKS-SECBINFHSA-N
Wikipedia
Roles Classification
Chemical Role:
environmental contaminant  Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Roles:
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).
serine proteinase inhibitor  An exogenous or endogenous compound which inhibits serine endopeptidases.
xenobiotic  A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application:
hypoglycemic agent  A drug which lowers the blood glucose level.
ChEBI Ontology
Outgoing Relation(s)
sitagliptin (CHEBI:40237) has role EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor (CHEBI:68612)
sitagliptin (CHEBI:40237) has role environmental contaminant (CHEBI:78298)
sitagliptin (CHEBI:40237) has role hypoglycemic agent (CHEBI:35526)
sitagliptin (CHEBI:40237) has role serine proteinase inhibitor (CHEBI:48353)
sitagliptin (CHEBI:40237) has role xenobiotic (CHEBI:35703)
sitagliptin (CHEBI:40237) is a triazolopyrazine (CHEBI:48277)
sitagliptin (CHEBI:40237) is a trifluorobenzene (CHEBI:83576)
Incoming Relation(s)
(1S,2R,5S)-5-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-2-(2,4,5-trifluorophenyl)cyclohexanamine (CHEBI:39959) has functional parent sitagliptin (CHEBI:40237)
IUPAC Name 
(3R)-3-amino-1-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
INNs  Source
sitagliptinWHO MedNet
sitagliptineWHO MedNet
sitagliptinaWHO MedNet
sitagliptinumWHO MedNet
Synonyms  Source
(2R)-4-OXO-4-[3-(TRIFLUOROMETHYL)-5,6-DIHYDRO[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7(8H)-YL]-1-(2,4,5-TRIFLUOROPHENYL)BUTAN-2-AMINEPDBeChem
MK-0431DrugBank
Manual XrefsDatabases
715PDBeChem
DB01261DrugBank
SitagliptinWikipedia
D08516KEGG DRUG
HMDB0015390HMDB
LSM-5363LINCS
2448DrugCentral
Registry NumbersSources
Reaxys:9962060Reaxys
CAS:486460-32-6ChemIDplus
Citations