Bedaquiline

Bedaquiline
Clinical data
Trade namesSirturo
Other namesBedaquiline fumarate,[1] TMC207,[2] R207910, AIDS222089
AHFS/Drugs.comMonograph
MedlinePlusa613022
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding>99.9%[6]
MetabolismLiver, by CYP3A4[7]
Elimination half-life5.5 months[7]
Excretionfecal[7]
Identifiers
  • (1R,2S)-1-(6-Bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenylbutan-2-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC32H31BrN2O2
Molar mass555.516 g·mol−1
3D model (JSmol)
  • Brc1ccc2nc(OC)c(cc2c1)[C@@H](c3ccccc3)[C@](O)(c5c4ccccc4ccc5)CCN(C)C
  • 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
  • Key:QUIJNHUBAXPXFS-XLJNKUFUSA-N

Bedaquiline, sold under the brand name Sirturo, is a medication used for the treatment of active tuberculosis.[1] Specifically, it is used to treat multi-drug-resistant tuberculosis along with other medications for tuberculosis.[1][8][9] It is taken by mouth.[3]

Common side effects include nausea, joint pains, headaches, and chest pain.[1] Serious side effects include QT prolongation, liver dysfunction, and an increased risk of death.[1] While harm during pregnancy has not been found, it has not been well studied in this population.[10] It is in the diarylquinoline antimycobacterial class of medications.[1] It works by blocking the ability of M. tuberculosis to make adenosine 5'-triphosphate (ATP).[1]

Bedaquiline was approved for medical use in the United States in 2012.[1] It is on the World Health Organization's List of Essential Medicines.[11]

  1. ^ a b c d e f g h "Bedaquiline Fumarate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  2. ^ Diacon AH, Pym A, Grobusch M, Patientia R, Rustomjee R, Page-Shipp L, et al. (June 2009). "The diarylquinoline TMC207 for multidrug-resistant tuberculosis". The New England Journal of Medicine. 360 (23): 2397–405. doi:10.1056/NEJMoa0808427. PMID 19494215.
  3. ^ a b "Sirturo- bedaquiline fumarate tablet". DailyMed. 17 October 2023. Archived from the original on 19 April 2024. Retrieved 20 April 2024.
  4. ^ "Sirturo EPAR". European Medicines Agency. 26 August 2005. Archived from the original on 18 March 2024. Retrieved 18 March 2024.
  5. ^ "Sirturo Product information". Union Register of medicinal products. 7 March 2014. Archived from the original on 18 March 2024. Retrieved 18 March 2024.
  6. ^ "Sirturo: Clinical Pharmacology". Archived from the original on 28 February 2015. Retrieved 28 April 2014.
  7. ^ a b c "Bedaquiline". Archived from the original on 20 May 2013. Retrieved 28 April 2014.
  8. ^ "WHO Rapid Communication: Key changes to treatment of multidrug- and rifampicin-resistant tuberculosis (MDR/RR-TB)". World Health Organization (WHO). Archived from the original on 20 August 2018. Retrieved 24 April 2019.
  9. ^ Ahmad N, Ahuja SD, Akkerman OW, Alffenaar JC, Anderson LF, Baghaei P, et al. (Collaborative Group for the Meta-Analysis of Individual Patient Data in MDR-TB treatment–2017) (September 2018). "Treatment correlates of successful outcomes in pulmonary multidrug-resistant tuberculosis: an individual patient data meta-analysis". Lancet. 392 (10150): 821–834. doi:10.1016/S0140-6736(18)31644-1. PMC 6463280. PMID 30215381.
  10. ^ "Bedaquiline (Sirturo) Use During Pregnancy". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  11. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.