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

General Information of Drug (ID: DR0182)
Drug Name
Bedaquiline fumarate
Synonyms
Bedaquiline (fumarate); Bedaquiline fumarate; Bedaquiline fumarate (JAN/USAN); Bedaquiline fumarate [USAN]; CHEBI:72295; CHEMBL2105700; CS-2922; D09873; EX-A2647; HY-14881A; P04QX2C1A5; R 403323; R-403323; R403323; SCHEMBL20496928; Sirturo; Sirturo (TN); UNII-P04QX2C1A5; (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol bis[(2Z)-but-2-enedioate]; 845533-86-0; AC-28750
Indication Pulmonary tuberculosis [ICD11: 1B10] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 671.6 Topological Polar Surface Area 120
Heavy Atom Count 45 Rotatable Bond Count 10
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
24812732
ChEBI ID
CHEBI:72295
CAS Number
845533-86-0
TTD Drug ID
D0Y4QG
Formula
C36H35BrN2O6
Canonical SMILES
CN(C)CCC(C1=CC=CC2=CC=CC=C21)(C(C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O.C(=CC(=O)O)C(=O)O
InChI
1S/C32H31BrN2O2.C4H4O4/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3;5-3(6)1-2-4(7)8/h4-17,20-21,30,36H,18-19H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t30-,32-;/m1./s1
InChIKey
ZLVSPMRFRHMMOY-WWCCMVHESA-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
Bedaquiline fumarate Metabolite M2 DM005650 N. A. Oxidation - N-demethylation 1 [2] , [3]
Bedaquiline fumarate Metabolite M5 DM005647 N. A. Unclear 1 [2] , [3]
N-desmethyl BDQ (M1) DM005652 N. A. Oxidation - N-demethylation 1 [2] , [3]
Bedaquiline fumarate Metabolite M3 DM005651 N. A. Oxidation - N-demethylation 2 [2] , [3]
Bedaquiline fumarate Metabolite M5-oxime DM005648 N. A. Oxidation - N-dealkylation 2 [2] , [3]
Bedaquiline fumarate Metabolite M6 DM005649 N. A. Unclear 2 [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006024 Bedaquiline fumarate Bedaquiline fumarate Metabolite M5 Unclear Unclear [2], [3]
MR006027 Bedaquiline fumarate Bedaquiline fumarate Metabolite M2 Oxidation - N-demethylation CYP3A4 [2], [3]
MR006029 Bedaquiline fumarate N-desmethyl BDQ (M1) Oxidation - N-demethylation CYP3A4 ... [2], [3]
MR006028 Bedaquiline fumarate Metabolite M2 Bedaquiline fumarate Metabolite M3 Oxidation - N-demethylation Unclear [2], [3]
MR006025 Bedaquiline fumarate Metabolite M5 Bedaquiline fumarate Metabolite M5-oxime Oxidation - N-dealkylation Unclear [2], [3]
MR006026 Bedaquiline fumarate Metabolite M5 Bedaquiline fumarate Metabolite M6 Unclear Unclear [2], [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2] , [3]
References
1 Bedaquiline Fumarate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Bedaquiline metabolism: enzymes and novel metabolites. Drug Metab Dispos. 2014 May;42(5):863-6.
3 Effects of Rifamycin Coadministration on Bedaquiline Desmethylation in Healthy Adult Volunteers

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