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

General Information of Drug (ID: DR0295)
Drug Name
Chenodeoxycholic acid
Synonyms
Chenodeoxycholate; Chenodesoxycholic acid; Chenodesoxycholsaeure; Chenodesoxycholsaeure [German]; Chenodiol; Chenodiol [USAN]; Chenofalk; Gallodesoxycholic acid; Henohol; Sodium chenodeoxycholate; Acide chenodeoxycholique; Acido chenodeoxicholico; Acidum chenodeoxycholicum; Anthropodeoxycholic acid; Anthropodesoxycholic acid; Anthropododesoxycholic acid; Chendol; Chenic acid; Chenique Acid; Chenix; Xenbilox; chenodeoxycholic acid; 3alpha,7alpha-Dihydroxy-5beta-cholan-24-oic acid; 474-25-9; 7-alpha-Hydroxylithocholic acid; Cdca
Indication Cholelithiasis [ICD11: DC11] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 392.6 Topological Polar Surface Area 77.8
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
10133
ChEBI ID
CHEBI:16755
CAS Number
474-25-9
TTD Drug ID
D03ZTE
Formula
C24H40O4
Canonical SMILES
CC(CCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
InChI
1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
InChIKey
RUDATBOHQWOJDD-BSWAIDMHSA-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
7alpha-hydroxy-3-oxo-5beta-cholan-24-oic Acid DM001802
5283932
Oxidation - Oxidation 1 [2]
Chenodeoxycholic acid glucuronide DM019930 N. A. Unclear 1 [4]
Chenodeoxycholic acid sulfolithocholyl metabolite DM001804 N. A. Unclear 1 [2]
Cholic acid DM004937
221493
Unclear 1 [3]
Gamma-muricholic acid DM001803
98205
Unclear 1 [2]
LCA DM001801
9903
Unclear 1 [2]
Taurine DM003084
1123
Unclear 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002540 Chenodeoxycholic acid Lithocholic acid Unclear Unclear [2]
MR002541 Chenodeoxycholic acid 7alpha-hydroxy-3-oxo-5beta-cholan-24-oic Acid Oxidation - Oxidation CYP3A4 ... [2]
MR002542 Chenodeoxycholic acid Gamma-muricholic acid Unclear CYP3A5 [2]
MR002543 Chenodeoxycholic acid Chenodeoxycholic acid sulfolithocholyl metabolite Unclear CYP2C9 [2]
MR002544 Chenodeoxycholic acid Taurine Unclear Unclear [2]
MR002545 Chenodeoxycholic acid Cholic acid Unclear CYP8B1 [3]
MR002546 Chenodeoxycholic acid Chenodeoxycholic acid glucuronide Unclear UGT1A3 [4]
⏷ 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
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 8B1 (CYP8B1) DME0631 Homo sapiens
CP8B1_HUMAN
1.14.18.8
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[4]
References
1 Chenodeoxycholic Acid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of human hepatic cytochrome p450 enzymes involved in the biotransformation of cholic and chenodeoxycholic acid. Drug Metab Dispos. 2008 Oct;36(10):1983-91.
3 Conversion of chenodeoxycholic acid to cholic acid by human CYP8B1. Biol Chem. 2019 Apr 24;400(5):625-628.
4 Human UDP-glucuronosyltransferase (UGT)1A3 enzyme conjugates chenodeoxycholic acid in the liver. Hepatology. 2006 Nov;44(5):1158-70.

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