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

General Information of Drug (ID: DR1856)
Drug Name
MPC-4326
Synonyms
Bevirimat; Bevirimat [INN]; PA-457; S125DW66N8; YK FH312; YK-FH312; bevirimatum; (3beta)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid; 174022-42-5; 3-O-(3',3'-Dimethylsuccinyl)-betulinic acid; 3-O-(3',3'-Dimethylsuccinyl)betulinic acid; 3-O-(3',3'-dimethylsuccinyl) betulinic acid; BVM; C36H56O6; CHEBI:65484; CHEMBL404519; DSB; Lup-20(29)-en-28-oic acid, 3-(3-carboxy-3-methyl-1-oxobutoxy)-, (3beta)-; UNII-S125DW66N8
Indication Human immunodeficiency virus infection [ICD11: 1C60] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 584.8 Topological Polar Surface Area 101
Heavy Atom Count 42 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
457928
ChEBI ID
CHEBI:65484
CAS Number
174022-42-5
TTD Drug ID
D04MPB
Formula
C36H56O6
Canonical SMILES
CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C)C(=O)O
InChI
1S/C36H56O6/c1-21(2)22-12-17-36(30(40)41)19-18-34(8)23(28(22)36)10-11-25-33(7)15-14-26(42-27(37)20-31(3,4)29(38)39)32(5,6)24(33)13-16-35(25,34)9/h22-26,28H,1,10-20H2,2-9H3,(H,38,39)(H,40,41)/t22-,23+,24-,25+,26-,28+,33-,34+,35+,36-/m0/s1
InChIKey
YJEJKUQEXFSVCJ-WRFMNRASSA-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
Di-BVMG DM017952 N. A. Conjugation - Glucuronidation 1 [3]
Mono-BVMG () DM017951 N. A. Conjugation - Glucuronidation 1 [3]
Mono-BVMG () DM017950 N. A. Conjugation - Glucuronidation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009658 MPC-4326 Mono-BVMG () Conjugation - Glucuronidation UGT2B7 ... [3]
MR009659 MPC-4326 Mono-BVMG () Conjugation - Glucuronidation UGT2B7 [3]
MR009660 MPC-4326 Di-BVMG Conjugation - Glucuronidation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 ClinicalTrials.gov (NCT00967187) Safety and Efficacy Study of MPC-4326 for Treatment of Patients With HIV-1 Infection..
2 Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19(3):107-13.
3 Glucuronidation of anti-HIV drug candidate bevirimat: identification of human UDP-glucuronosyltransferases and species differences

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