Bedaquiline
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MedKoo CAT#: 314214

CAS#: 843663-66-1 (free base)

Description: Bedaquiline, also known as TMC207 and R207910, is a diarylquinoline anti-tuberculosis drug, which was discovered by a team led by Koen Andries at Janssen Pharmaceutica. Bedaquiline blocks the proton pump for ATP synthase of mycobacteria. ATP production is required for cellular energy production and its loss leads to cell death, even in dormant or nonreplicating mycobacteria.It is the first member of a new class of drugs called the diarylquinolines. Bedaquiline is bactericidal.


Chemical Structure

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Bedaquiline
CAS# 843663-66-1 (free base)

Theoretical Analysis

MedKoo Cat#: 314214
Name: Bedaquiline
CAS#: 843663-66-1 (free base)
Chemical Formula: C32H31BrN2O2
Exact Mass: 554.15689
Molecular Weight: 555.5
Elemental Analysis: C, 69.19; H, 5.62; Br, 14.38; N, 5.04; O, 5.76

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 Same day
200.0mg USD 250.0 Same day
500.0mg USD 550.0 Same day
1.0g USD 950.0 Same day
2.0g USD 1750.0 Same day
5.0g USD 3150.0 Same day
10.0g USD 5950.0 2 weeks
20.0g USD 7950.0 2 weeks
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Related CAS #: 843663-66-1 (free base)   845533-86-0 (fumarate)    

Synonym: TMC207; TMC-207; TMC 207; R207910; R-207910; R 207910; Bedaquiline; Bedaquiline fumarate; trade name Sirturo,

IUPAC/Chemical Name: (1R,2S)-1-(6-Bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol

InChi Key: QUIJNHUBAXPXFS-XLJNKUFUSA-N

InChi Code: InChI=1S/C32H31BrN2O2/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/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1

SMILES Code: O[C@](CCN(C)C)(C1=C2C=CC=CC2=CC=C1)[C@@H](C3=CC4=CC(Br)=CC=C4N=C3OC)C5=CC=CC=C5

Appearance: solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, DMF, EtOH, and 1:3 DMF:PBS

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 555.5 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Hafkin J, Hittel N, Martin A, Gupta R. Compassionate Use of Delamanid in Combination with Bedaquiline for the Treatment of MDR-TB. Eur Respir J. 2018 Oct 25. pii: 1801154. doi: 10.1183/13993003.01154-2018. [Epub ahead of print] PubMed PMID: 30361253.

2: Ndjeka N, Schnippel K, Master I, Meintjes G, Maartens G, Romero R, Padanilam X, Enwerem M, Chotoo S, Singh N, Hughes J, Variava E, Ferreira H, Te Riele J, Ismail N, Mohr E, Bantubani N, Conradie F. High treatment success rate for multidrug-resistant and extensively drug-resistant tuberculosis using a bedaquiline-containing treatment regimen. Eur Respir J. 2018 Oct 25. pii: 1801528. doi: 10.1183/13993003.01528-2018. [Epub ahead of print] PubMed PMID: 30361246.

3: Lopez B, Siqueira de Oliveira R, Pinhata JMW, Chimara E, Pacheco Ascencio E, Puyén Guerra ZM, Wainmayer I, Simboli N, Del Granado M, Palomino JC, Ritacco V, Martin A. Bedaquiline and linezolid MIC distributions and epidemiological cut-off values for Mycobacterium tuberculosis in the Latin American region. J Antimicrob Chemother. 2018 Oct 25. doi: 10.1093/jac/dky414. [Epub ahead of print] PubMed PMID: 30358851.

4: Fan Q, Ming WK, Yip WY, You JHS. Cost-effectiveness of bedaquiline or delamanid plus background regimen for multidrug-resistant tuberculosis in a high-income intermediate burden city of China. Int J Infect Dis. 2018 Oct 17. pii: S1201-9712(18)34553-3. doi: 10.1016/j.ijid.2018.10.007. [Epub ahead of print] PubMed PMID: 30342251.

5: Richard M, Gutiérrez AV, Viljoen A, Rodriguez-Rincon D, Roquet-Baneres F, Blaise M, Everall I, Parkhill J, Floto RA, Kremer L. Mutations in the MAB_2299c TetR regulator confer cross-resistance to clofazimine and bedaquiline in Mycobacterium abscessus. Antimicrob Agents Chemother. 2018 Oct 15. pii: AAC.01316-18. doi: 10.1128/AAC.01316-18. [Epub ahead of print] PubMed PMID: 30323043.

6: Ismail N, Omar SV, Ismail NA, Peters RPH. Collated data of mutation frequencies and associated genetic variants of bedaquiline, clofazimine and linezolid resistance in Mycobacterium tuberculosis. Data Brief. 2018 Sep 24;20:1975-1983. doi: 10.1016/j.dib.2018.09.057. eCollection 2018 Oct. PubMed PMID: 30306102; PubMed Central PMCID: PMC6172430.

7: Chawla K, Martinez E, Kumar A, Shenoy VP, Sintchenko V. Whole-genome sequencing reveals genetic signature of bedaquiline resistance in a clinical isolate of Mycobacterium tuberculosis. J Glob Antimicrob Resist. 2018 Sep 21;15:103-104. doi: 10.1016/j.jgar.2018.09.006. [Epub ahead of print] PubMed PMID: 30248414.

8: Park S, Lee KM, Kim I, Mok J. The use of bedaquiline to treat patients with multidrug-resistant tuberculosis and end-stage renal disease: A case report. Int J Infect Dis. 2018 Nov;76:88-90. doi: 10.1016/j.ijid.2018.09.009. Epub 2018 Sep 19. PubMed PMID: 30244076.

9: Erratum: Delamanid, Bedaquiline, and Linezolid Minimum Inhibitory Concentration Distributions and Resistance-related Gene Mutations in Multidrug-resistant and Extensively Drug-resistant Tuberculosis in Korea. Ann Lab Med. 2019 Jan;39(1):113. doi: 10.3343/alm.2019.39.1.113. PubMed PMID: 30215242; PubMed Central PMCID: PMC6143465.

10: Rawal T, Patel S, Butani S. Chitosan nanoparticles as a promising approach for pulmonary delivery of bedaquiline. Eur J Pharm Sci. 2018 Nov 1;124:273-287. doi: 10.1016/j.ejps.2018.08.038. Epub 2018 Aug 31. PubMed PMID: 30176365.

11: Zhao Y, Fox T, Manning K, Stewart A, Tiffin N, Khomo N, Leslie J, Boulle A, Mudaly V, Kock Y, Meintjes G, Wasserman S. Improved treatment outcomes with bedaquiline when substituted for second-line injectable agents in multidrug resistant tuberculosis: a retrospective cohort study. Clin Infect Dis. 2018 Aug 24. doi: 10.1093/cid/ciy727. [Epub ahead of print] PubMed PMID: 30165431.

12: Ismail N, Omar SV, Ismail NA, Peters RPH. In vitro approaches for generation of Mycobacterium tuberculosis mutants resistant to bedaquiline, clofazimine or linezolid and identification of associated genetic variants. J Microbiol Methods. 2018 Oct;153:1-9. doi: 10.1016/j.mimet.2018.08.011. Epub 2018 Aug 28. PubMed PMID: 30165087.

13: Borisov SE, D'Ambrosio L, Centis R, Tiberi S, Dheda K, Alffenaar JW, Amale R, Belilowski E, Bruchfeld J, Canneto B, Denholm J, Duarte R, Esmail A, Filippov A, Davies Forsman L, Gaga M, Ganatra S, Igorevna GA, Lazaro Mastrapa B, Manfrin V, Manga S, Maryandyshev A, Massard G, González Montaner P, Mullerpattan J, Palmero DJ, Pontarelli A, Papavasileiou A, Pontali E, Romero Leyet R, Spanevello A, Udwadia ZF, Viggiani P, Visca D, Sotgiu G, Migliori GB. Outcomes of patients with drug-resistant-tuberculosis treated with bedaquiline-containing regimens and undergoing adjunctive surgery. J Infect. 2018 Aug 7. pii: S0163-4453(18)30246-9. doi: 10.1016/j.jinf.2018.08.003. [Epub ahead of print] PubMed PMID: 30096332.

14: Ionescu AM, Mpobela Agnarson A, Kambili C, Metz L, Kfoury J, Wang S, Williams A, Singh V, Thomas A. Bedaquiline- versus injectable-containing drug-resistant tuberculosis regimens: a cost-effectiveness analysis. Expert Rev Pharmacoecon Outcomes Res. 2018 Dec;18(6):677-689. doi: 10.1080/14737167.2018.1507821. Epub 2018 Aug 23. PubMed PMID: 30073886.

15: Martinez E, Hennessy D, Jelfs P, Crighton T, Chen SC, Sintchenko V. Mutations associated with in vitro resistance to bedaquiline in Mycobacterium tuberculosis isolates in Australia. Tuberculosis (Edinb). 2018 Jul;111:31-34. doi: 10.1016/j.tube.2018.04.007. Epub 2018 Apr 25. PubMed PMID: 30029911.

16: Yang JS, Kim KJ, Choi H, Lee SH. Delamanid, Bedaquiline, and Linezolid Minimum Inhibitory Concentration Distributions and Resistance-related Gene Mutations in Multidrug-resistant and Extensively Drug-resistant Tuberculosis in Korea. Ann Lab Med. 2018 Nov;38(6):563-568. doi: 10.3343/alm.2018.38.6.563. Erratum in: Ann Lab Med. 2019 Jan;39(1):113. PubMed PMID: 30027700; PubMed Central PMCID: PMC6056398.

17: Reuter A, Furin J. Bedaquiline use in South Africa reveals a lifesaving policy in action. Lancet Respir Med. 2018 Sep;6(9):653-655. doi: 10.1016/S2213-2600(18)30280-7. Epub 2018 Jul 11. PubMed PMID: 30001995.

18: Schnippel K, Ndjeka N, Maartens G, Meintjes G, Master I, Ismail N, Hughes J, Ferreira H, Padanilam X, Romero R, Te Riele J, Conradie F. Effect of bedaquiline on mortality in South African patients with drug-resistant tuberculosis: a retrospective cohort study. Lancet Respir Med. 2018 Sep;6(9):699-706. doi: 10.1016/S2213-2600(18)30235-2. Epub 2018 Jul 11. PubMed PMID: 30001994.

19: Schnippel K, Firnhaber C, Page-Shipp L, Sinanovic E. Impact of adverse drug reactions on the incremental cost-effectiveness of bedaquiline for drug-resistant tuberculosis. Int J Tuberc Lung Dis. 2018 Aug 1;22(8):918-925. doi: 10.5588/ijtld.17.0869. PubMed PMID: 29991402.

20: Bastard M, Guglielmetti L, Huerga H, Hayrapetyan A, Khachatryan N, Yegiazaryan L, Faqirzai J, Hovhannisyan L, Varaine F, Hewison C. Bedaquiline and Repurposed Drugs for Fluoroquinolone-Resistant Multidrug-Resistant Tuberculosis: How Much Better Are They? Am J Respir Crit Care Med. 2018 Nov 1;198(9):1228-1231. doi: 10.1164/rccm.201801-0019LE. PubMed PMID: 29969054.



Additional Information

When it was approved by the FDA on the 28th December 2012, it was the first new medicine to fight TB in more than forty years, and is specifically approved to treat multi-drug-resistant tuberculosis.