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

General Information of Drug (ID: DR1183)
Drug Name
Obeticholic acid
Synonyms
Obeticholic acid; Ocaliva; INT 747; INT-747; INT747; (4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid; 0462Z4S4OZ; 459789-99-2; 6-ECDCA; 6-ETHYL-CHENODEOXYCHOLIC ACID; 6-Ethyl-CDCA; 6-Ethylchenodeoxycholic acid; 6ECDCA; 6alpha-Ethyl-chenodeoxycholic acid; 6alpha-ethylchenodeoxycholic acid; DSP-1747; UNII-0462Z4S4OZ
Indication Cholangitis [ICD11: DC13] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 420.6 Topological Polar Surface Area 77.8
Heavy Atom Count 30 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
447715
PubChem SID
828938 ; 828951 ; 7886586 ; 7888489 ; 10300105 ; 14880306 ; 16101459 ; 17396626 ; 36889785 ; 46392814 ; 49700782 ; 53789454 ; 57404826 ; 76486275 ; 96026040 ; 103700141 ; 104638392 ; 123055342 ; 126680398 ; 135263637 ; 163122223 ; 175265866 ; 176236560 ; 178100437 ; 204383201 ; 219813737 ; 223670674 ; 224721644 ; 227005340 ; 251970994 ; 252300974 ; 252553933
ChEBI ID
CHEBI:43602
CAS Number
459789-99-2
TTD Drug ID
D0M4WA
Formula
C26H44O4
Canonical SMILES
CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCC(=O)O)C)C)O
InChI
1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1
InChIKey
ZXERDUOLZKYMJM-ZWECCWDJSA-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
Glyco-obeticholic acid DM002274
121322333
Conjugation - Taurine Conjugation 1 [3]
Tauro-Obeticholic acid DM002275
122201312
Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002860 Obeticholic acid Glyco-obeticholic acid Conjugation - Taurine Conjugation Unclear [3]
MR002861 Obeticholic acid Tauro-Obeticholic acid Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Bile acid-CoA thioesterase (BAAT) DME0200 Homo sapiens
BAAT_HUMAN
2.3.1.65
[2]
References
1 Obeticholic Acid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Glycine and taurine conjugation of bile acids by a single enzyme. Molecular cloning and expression of human liver bile acid CoA:amino acid N-acyltransferase. J Biol Chem. 1994 Jul 29;269(30):19375-9.
3 A novel LC-MS/MS method for simultaneous estimation of obeticholic acid, glyco-obeticholic acid, tauro-obeticholic acid in human plasma and its application to a pharmacokinetic study J Sep Sci. 2021 Apr;44(7):1307-1323. doi: 10.1002/jssc.202001050.

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