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

General Information of Drug (ID: DR0039)
Drug Name
Acetohexamide
Synonyms
Acetohexamid; Acetohexamida; Acetohexamida [INN-Spanish]; Acetohexamidum; Acetohexamidum [INN-Latin]; Dimelin; Dimelor; Dymelor; Gamadiabet; Hypoglicil; Metaglucina; Minoral; Ordimel; Tsiklamid; U-14812; acetohexamide; 1-((p-Acetylphenyl)sulfonyl)-3-cyclohexylurea; 1-(4-acetylphenyl)sulfonyl-3-cyclohexylurea; 1-(p-Acetylbenzenesulfonyl)-3-cyclohexylurea; 4-Acetyl-N-[(cyclohexylamino)carbonyl]benzenesulfonamide; 968-81-0; CCRIS 4; HSDB 3280; N-(p-Acetylphenylsulfonyl)-N'-cyclohexylurea; NCI-C03247; UNII-QGC8W08I6I
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 324.4 Topological Polar Surface Area 101
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
1989
PubChem SID
9025 ; 4560832 ; 7847286 ; 8144406 ; 8151368 ; 10321105 ; 11110689 ; 11112460 ; 11466083 ; 11467203 ; 11485866 ; 15347370 ; 17390067 ; 17404651 ; 24278077 ; 26752942 ; 29221177 ; 46505821 ; 47216939 ; 47440426 ; 47662475 ; 47810929 ; 48185152 ; 48413134 ; 48415505 ; 48422764 ; 48424779 ; 49698323 ; 49856121 ; 50105548 ; 50105549 ; 50271749 ; 53777194 ; 56463352 ; 57321086 ; 57653828 ; 85083217 ; 85230885 ; 85787831 ; 90341130 ; 92125175 ; 92303511 ; 92307991 ; 99222786 ; 103590218 ; 103913586 ; 104171099 ; 104299291 ; 121360822 ; 121362846
ChEBI ID
ChEBI:28052
CAS Number
968-81-0
TTD Drug ID
D07WFK
Formula
C15H20N2O4S
Canonical SMILES
CC(=O)NC1=CC=C(C=C1)O
InChI
1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)
InChIKey
VGZSUPCWNCWDAN-UHFFFAOYSA-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
4-trans-hydroxyacetohexamide DM000609
164125847
Oxidation - Hydroxylation 1 [4]
4-trans-hydroxyhydroxyhexamide DM000610 N. A. Oxidation - Hydroxylation 1 [4]
Hydroxyhexamide DM000608
18497
Oxidation - Hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002795 Acetohexamide Hydroxyhexamide Oxidation - Hydroxylation Unclear [4]
MR002796 Acetohexamide 4-trans-hydroxyacetohexamide Oxidation - Hydroxylation Unclear [4]
MR002797 Acetohexamide 4-trans-hydroxyhydroxyhexamide Oxidation - Hydroxylation Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Short-chain dehydrogenase/reductase retSDR1 (DHRS3) DME0414 Homo sapiens
DHRS3_HUMAN
1.1.1.300
[3]
References
1 Acetohexamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinically and pharmacologically relevant interactions of antidiabetic drugs. Ther Adv Endocrinol Metab. 2016 Apr;7(2):69-83.
3 Molecular and biochemical characterisation of human short-chain dehydrogenase/reductase member 3 (DHRS3). Chem Biol Interact. 2015 Jun 5;234:178-87.
4 Metabolism, blood levels and rate of excretion of acetohexamide in human subjects Diabetes. 1967 Feb;16(2):118-27. doi: 10.2337/diab.16.2.118.

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