User Survey : Help improve ChEBI - please click here to take part in our quick User Survey.

CHEBI:40237 - sitagliptin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name sitagliptin
ChEBI ID CHEBI:40237
Definition A triazolopyrazine that exhibits hypoglycemic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Save molfile Download Molfile
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C16H15F6N5O
Net Charge 0
Average Mass 407.31382
Monoisotopic Mass 407.118
InChI InChI=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
InChIKey MFFMDFFZMYYVKS-SECBINFHSA-N
SMILES N[C@@H](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)Cc1cc(F)c(F)cc1F
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): serine proteinase inhibitor
An exogenous or endogenous compound which inhibits serine endopeptidases.
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).
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(s): hypoglycemic agent
A drug which lowers the blood glucose level.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 (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 Sources
sitagliptin WHO MedNet
sitagliptina WHO MedNet
sitagliptine WHO MedNet
sitagliptinum WHO MedNet
Synonyms Sources
(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-AMINE PDBeChem
MK-0431 DrugBank
Database Links Databases
715 PDBeChem
D08516 KEGG DRUG
DB01261 DrugBank
HMDB15390 HMDB
LSM-5363 LINCS
Sitagliptin Wikipedia
View more database links
Registry Numbers Types Sources
486460-32-6 CAS Registry Number ChemIDplus
9962060 Reaxys Registry Number Reaxys
9962060 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
23286208 PubMed citation Europe PMC
23331339 PubMed citation Europe PMC
23432786 PubMed citation Europe PMC
23489256 PubMed citation Europe PMC
23927568 PubMed citation Europe PMC
24039399 PubMed citation Europe PMC
24041927 PubMed citation Europe PMC
Last Modified
25 February 2016
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag