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

General Information of Drug (ID: DR0311)
Drug Name
Chlorpropamide
Synonyms
Chlorodiabina; Chloronase; Chloropropamide; Chlorpropamid; Chlorpropamidum; Clorpropamid; Clorpropamida; Clorpropamide; Adiaben; Asucrol; Bioglumin; Catanil; Diabaril; Diabechlor; Diabenal; Diabenese; Diabeneza; Diabet-Pages; Diabetoral; Diabexan; Diabinese; Diamel Ex; Dynalase; Glisema; Glucamide; Insulase; Meldian; Melitase; Mellinese; Millinese; Oradian; Prodiaben; Stabinol; chlorpropamide; 1-(4-Chlorophenylsulfonyl)-3-propylurea; 1-(p-Chlorobenzenesulfonyl)-3-propylurea; 4-chloro-N-(propylcarbamoyl)benzenesulfonamide; 94-20-2
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 276.74 Topological Polar Surface Area 83.6
Heavy Atom Count 17 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2727
PubChem SID
98709 ; 228495 ; 493093 ; 855559 ; 4332428 ; 7847337 ; 7978927 ; 8149254 ; 8151765 ; 10321644 ; 10538465 ; 11110918 ; 11110919 ; 11335688 ; 11360927 ; 11363038 ; 11364687 ; 11365600 ; 11367249 ; 11368162 ; 11369811 ; 11371333 ; 11372852 ; 11373947 ; 11375411 ; 11376324 ; 11377974 ; 11461899 ; 11466351 ; 11467471 ; 11483754 ; 11485982 ; 11487905 ; 11490163 ; 11492099 ; 11493958 ; 15141440 ; 17389965 ; 17404792 ; 24277701 ; 26611658 ; 26679951 ; 26746910 ; 26746911 ; 26751448 ; 29221883 ; 46506402 ; 47216742 ; 47515283 ; 47515284
ChEBI ID
CHEBI:3650
CAS Number
94-20-2
TTD Drug ID
D00BCP
Formula
C10H13ClN2O3S
Canonical SMILES
CCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)Cl
InChI
1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)
InChIKey
RKWGIWYCVPQPMF-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
2-hydroxychlorpropamide DM001830
3082454
Oxidation - 2-Hydroxylation 1 [3]
2-OH-chlorpropamide DM001832
131750723
Oxidation - Hydroxylation 1 [3]
3-hydroxychlorpropamide DM001831
131750724
Oxidation - 2-Hydroxylation 1 [3]
4-Chlorobenzenesulfonylurea DM001828
89785
Oxidation - N-Dealkylation 1 [3]
4-Chlorobenzenesulfonamide DM001829
66824
Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000647 Chlorpropamide 4-Chlorobenzenesulfonylurea Oxidation - N-Dealkylation Unclear [3]
MR000648 Chlorpropamide 2-hydroxychlorpropamide Oxidation - 2-Hydroxylation CYP2C9 ... [3]
MR000649 Chlorpropamide 3-hydroxychlorpropamide Oxidation - 2-Hydroxylation CYP2D6 [3]
MR000650 Chlorpropamide 2-OH-chlorpropamide Oxidation - Hydroxylation CYP2C9 ... [3]
MR000646 4-Chlorobenzenesulfonylurea 4-Chlorobenzenesulfonamide Unclear Unclear [3]
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Chlorpropamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Chlorpropamide 2-hydroxylation is catalysed by CYP2C9 and CYP2C19 in vitro: chlorpropamide disposition is influenced by CYP2C9, but not by CYP2C19 genetic polymorphism. Br J Clin Pharmacol. 2005 May;59(5):552-63.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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