Product Name

Bedaquiline fumarate

CAS Number

845533-86-0

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Product Name:
Bedaquiline fumarate
CAS Number:
845533-86-0
Indication:
Bedaquiline is indicated as part of combination therapy in adults (≥ 18 years) with pulmonary multi-drug resistant tuberculosis (MDR-TB).
Mode of Action:

Bedaquiline is a diarylquinoline antimycobacterial drug that inhibits the proton pump of mycobacterial ATP (adenosine 5'-triphosphate) synthase, an enzyme that is essential for the generation of energy in Mycobacterium tuberculosis. Bacterial death occurs as a result of bedaquiline.

Pharmacodynamics:

Bedaquiline is primarily subjected to oxidative metabolism leading to the formation of N-monodesmethyl metabolite (M2). M2 is not thought to contribute significantly to clinical efficacy given its lower average exposure (23% to 31%) in humans and lower antimycobacterial activity (4 to 6-fold lower) compared to the parent compound. M2 concentrations appeared to correlate with QT prolongation. Bedaquiline inhibits mycobacterial TB at a minimal inhibitory concentration (MIC) from 0.002-0.06 μg/ml and with a MIC50 of 0.03 μg/ml. Furthermore, bacteria that have smaller ATP stores (usually in dormant, nonreplicating bacilli) are more susceptible to bedaquiline.

Metabolism:

Bedaquiline is hepatically metabolized. The main enzyme involved is CYP3A4 which metabolizes bedaquiline into the N-monodesmethyl metabolite (M2). This metabolite is 4 to 6-times less active in terms of antimycobacterial potency.

Toxicity:

The most common adverse reactions reported in ≥10% of patients treated with bedaquiline are nausea, arthralgia, and headache.

IUPAC:
3-Quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl- -phenyl-, (S, R)-, (2E)-2-butenedioate (1:1) (salt)
ATC:
J04AK05
DrugBank:
DB08903
Formula:
C32H31BrN2O2
Molecular Mass:
671.5845
Synonyms:
Bedaquiline fumarate, R403323, Sirturo, UNII-P04QX2C1A5
SMILES:
CN(C)CC[C@@](c1cccc2c1cccc2)([C@H](c3ccccc3)c4cc5cc(ccc5nc4OC)Br)O.C(=C/C(=O)O)C(=O)O
AHFS Code:
08:16.0
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
General Reference:
General Reference:

  1. Matteelli A, Carvalho AC, Dooley KE, Kritski A: TMC207: the first compound of a new class of potent anti-tuberculosis drugs. Future Microbiol. 2010 Jun;5(6):849-58. doi: 10.2217/fmb.10.50. Pubmed

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