Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1490)
Drug Name
Sitagliptin
Synonyms
Sitagliptan; Sitagliptin; Sitagliptin phosphate; Tesavel; Xelevia; Januvia; MK-0431; QFP0P1DV7Z; (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; (3R)-3-AMINO-1-[3-(TRIFLUOROMETHYL)-5H,6H,7H,8H-[1,2,4]TRIAZOLO[4,3-A]PYRAZIN-7-YL]-4-(2,4,5-TRIFLUOROPHENYL)BUTAN-1-ONE; (R)-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; 486460-32-6; CHEBI:40237; UNII-QFP0P1DV7Z
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 407.31 Topological Polar Surface Area 77
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
4369359
PubChem SID
7885474 ; 9656038 ; 14904024 ; 16466401 ; 35668584 ; 46393524 ; 46505822 ; 46511716 ; 46513917 ; 46530623 ; 48034814 ; 50070925 ; 56365842 ; 78231257 ; 85789641 ; 92307950 ; 96025201 ; 99443685 ; 103502876 ; 112947540 ; 117695427 ; 126669712 ; 126731480 ; 134337929 ; 135206675 ; 136339733 ; 137005783 ; 143037551 ; 143497677 ; 152028143 ; 152164204 ; 152164205 ; 152238548 ; 152344340 ; 160646743 ; 160964592 ; 162201432 ; 164784279 ; 164824529 ; 164846813 ; 165235282 ; 165245552 ; 165702336 ; 170499559 ; 174006349 ; 174529510 ; 175268642 ; 178102906 ; 179231014 ; 186005103
ChEBI ID
ChEBI:40237
CAS Number
486460-32-6
TTD Drug ID
D0U2JP
Formula
C16H15F6N5O
Canonical SMILES
C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Sitagliptin M1 Metabolite DM006352
46782925
Conjugation - Sulfation 1 [3]
Sitagliptin M2 and M5 Metabolites DM006353 N. A. Other reaction - Cyclization 1 [3]
Sitagliptin M6 Metabolite DM006350
87621734
Oxidation - Carbamoylation 1 [3]
Sitagliptin M4 Metabolite DM006351 N. A. Conjugation - O-glucuronidation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006817 Sitagliptin Sitagliptin M6 Metabolite Oxidation - Carbamoylation CYP3A4 ... [3]
MR006819 Sitagliptin Sitagliptin M1 Metabolite Conjugation - Sulfation CYP3A4 ... [3]
MR006820 Sitagliptin Sitagliptin M2 and M5 Metabolites Other reaction - Cyclization CYP3A4 ... [3]
MR006818 Sitagliptin M6 Metabolite Sitagliptin M4 Metabolite Conjugation - O-glucuronidation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Sitagliptin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetics of dipeptidylpeptidase-4 inhibitors. Diabetes Obes Metab. 2010 Aug;12(8):648-58.
3 Metabolism and excretion of the dipeptidyl peptidase 4 inhibitor [14C]sitagliptin in humans

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