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

General Information of Drug (ID: DR5758)
Drug Name
Vildagliptin
Synonyms
Equa; Galvu; Galvus; Jalra; Xiliarx; Galvus (TN); Vidagliptin (see Vildagliptin); Vildagliptin (JAN/USAN/INN); (2S)-(((3-hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrile; (2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile; 1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile; 2-Pyrrolidinecarbonitrile, 1-[[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-, (2S)-(9CI)
Indication Type-2 diabetes [ICD11: 5A11] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 303.4 Topological Polar Surface Area 76.4
Heavy Atom Count 22 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
6918537
ChEBI ID
CHEBI:135285
CAS Number
274901-16-5
TTD Drug ID
D0L3DK
Formula
C17H25N3O2
Canonical SMILES
C1C[C@H](N(C1)C(=O)CNC23CC4CC(C2)CC(C4)(C3)O)C#N
InChI
InChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2/t12?,13?,14-,16?,17?/m0/s1
InChIKey
SYOKIDBDQMKNDQ-XWTIBIIYSA-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
Vildagliptin M15.3 metabolite DM016231
60198109
Hydrolysis - Amide Hydrolysis 1 [4] , [5]
Vildagliptin M20.2 metabolite DM016601
133587905
Conjugation - Glucuronidation 1 [4] , [5] , [2]
Vildagliptin M20.7 metabolite DM016119
46783242
Hydrolysis - Hydrolysis 1 [4] , [5] , [2]
Vildagliptin M20.9 metabolite DM017482 N. A. Oxidation - Oxidation 1 [4] , [5]
Vildagliptin M21.6 metabolite DM016804
156028071
Reduction - Decarboxylation 1 [4] , [5]
Vildagliptin metabolite M14.2 DM017483 N. A. Unclear - Unclear 1 [5]
Vildagliptin metabolite M18.6 DM016279
68253625
Unclear - Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008779 Vildagliptin Vildagliptin M20.7 metabolite Hydrolysis - Hydrolysis DPP4 [4], [5], [2]
MR008780 Vildagliptin Vildagliptin M15.3 metabolite Hydrolysis - Amide Hydrolysis Unclear [4], [5]
MR008781 Vildagliptin Vildagliptin M20.2 metabolite Conjugation - Glucuronidation UGT2B7 [4], [5], [2]
MR008782 Vildagliptin Vildagliptin M20.9 metabolite Oxidation - Oxidation Unclear [4], [5]
MR008783 Vildagliptin Vildagliptin M21.6 metabolite Reduction - Decarboxylation Unclear [4], [5]
MR008784 Vildagliptin Vildagliptin metabolite M18.6 Unclear - Unclear Unclear [5]
MR008785 Vildagliptin Vildagliptin metabolite M14.2 Unclear - Unclear Unclear [5]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Dipeptidyl peptidase IV (DPP4) DME0133 Homo sapiens
DPP4_HUMAN
3.4.14.5
[2]
Dipeptidyl peptidase IV (DPP4) DME0133 Homo sapiens
DPP4_HUMAN
3.4.14.5
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6310).
2 Dipeptidyl peptidase-4 greatly contributes to the hydrolysis of vildagliptin in human liver
3 Mechanistic Study on the Effect of Renal Impairment on the Pharmacokinetics of Vildagliptin and its Carboxylic Acid Metabolite
4 Absorption, metabolism, and excretion of [14C]vildagliptin, a novel dipeptidyl peptidase 4 inhibitor, in humans
5 Disposition of vildagliptin, a novel dipeptidyl peptidase 4 inhibitor, in rats and dogs

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