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ChEBI
> Main
CHEBI:40237 - sitagliptin
Main
ChEBI Ontology
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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
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Read full article at Wikipedia
Formula
C16H15F6N5O
Net Charge
0
Average Mass
407.31382
Monoisotopic Mass
407.11808
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
(1
S
,2
R
,5
S
)-5-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-
a
]pyrazin-7(8
H
)-yl]-2-(2,4,5-trifluorophenyl)cyclohexanamine (
CHEBI:39959
)
has functional parent
sitagliptin (
CHEBI:40237
)
IUPAC Name
(3
R
)-
3-
amino-
1-
[3-
(trifluoromethyl)-
5,6-
dihydro[1,2,4]triazolo[4,3-
a
]pyrazin-
7(8
H
)-
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
Manual Xrefs
Databases
2448
DrugCentral
715
PDBeChem
D08516
KEGG DRUG
DB01261
DrugBank
HMDB0015390
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
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
22 February 2017
General Comment
2014-10-29
Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag