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

General Information of Drug (ID: DR3113)
Drug Name
Norbuprenorphine
Synonyms
Norbuprenorphine; N-Desalkylbuprenorphine; Des(cyclopropylmethyl)buprenorphine; UNII-7E53B4O073; 7E53B4O073; 6,14-Ethenomorphinan-7-methanol, alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (alphaS,5alpha,7alpha)-; AC1L3GBB; SCHEMBL14408877; CHEMBL1743323; YOYLLRBMGQRFTN-IOMBULRVSA-N; ZINC6031944; LS-67705; 6,14-ethenomorphinan-3-ol, 4,5-epoxy-18,19-dihydro-18-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-, (5alpha,6beta,14beta,18R)-
Indication Human immunodeficiency virus infection [ICD11: 1C60-1C62] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 413.5 Topological Polar Surface Area 71
Heavy Atom Count 30 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
114976
CAS Number
78715-23-8
Formula
C25H35NO4
Canonical SMILES
CC(C)(C)C(C)(C1CC23CCC1(C4C25CCNC3CC6=C5C(=C(C=C6)O)O4)OC)O
InChI
InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1
InChIKey
YOYLLRBMGQRFTN-IOMBULRVSA-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
Norbuprenorphine metabolite M1 DM017339 N. A. Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013758 Norbuprenorphine Norbuprenorphine metabolite M1 Unclear UGT1A3 ... [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 ClinicalTrials.gov (NCT02666001) A Study to Assess the Drug-drug Interaction of BMS 663068 With Methadone and Also With Buprenorphine/Naloxone
2 Chemical and enzyme-assisted syntheses of norbuprenorphine-3--D-glucuronide
3 Contribution of the different UDP-glucuronosyltransferase (UGT) isoforms to buprenorphine and norbuprenorphine metabolism and relationship with the main UGT polymorphisms in a bank of human liver microsomes. Drug Metab Dispos. 2010 Jan;38(1):40-5.

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