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Also known as: 845533-86-0, Bedaquiline (fumarate), Sirturo, R403323, Bedaquiline fumarate [usan], P04qx2c1a5
Molecular Formula
C36H35BrN2O6
Molecular Weight
671.6  g/mol
InChI Key
ZLVSPMRFRHMMOY-WWCCMVHESA-N
FDA UNII
P04QX2C1A5

Bedaquiline
1 2D Structure

Bedaquiline

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol;(E)-but-2-enedioic acid
2.1.2 InChI
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
2.1.3 InChI Key
ZLVSPMRFRHMMOY-WWCCMVHESA-N
2.1.4 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
2.1.5 Isomeric SMILES
CN(C)CC[C@@](C1=CC=CC2=CC=CC=C21)([C@H](C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O.C(=C/C(=O)O)\C(=O)O
2.2 Other Identifiers
2.2.1 UNII
P04QX2C1A5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (1r,2s)-1-(6-bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-(3-fluorophenyl)-1-phenyl-butan-2-ol

2. Aids-222089

3. Aids222088

4. Bedaquiline

5. R207910

6. Tmc207

2.3.2 Depositor-Supplied Synonyms

1. 845533-86-0

2. Bedaquiline (fumarate)

3. Sirturo

4. R403323

5. Bedaquiline Fumarate [usan]

6. P04qx2c1a5

7. Chebi:72295

8. 845533-86-0 (fumarate)

9. R-403323

10. R 403323

11. Unii-p04qx2c1a5

12. (1r,2s)-1-(6-bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol Fumarate

13. Bedaquilinefumarate

14. Sirturo (tn)

15. Chembl2105700

16. Schembl20496928

17. Bedaquiline Fumarate [mi]

18. Bedaquiline Fumarate; R403323

19. Bedaquiline Fumarate (jan/usan)

20. Bedaquiline Fumarate [jan]

21. Dtxsid401004837

22. Ex-a2647

23. Hy-14881a

24. S4854

25. Bedaquiline Fumarate [who-dd]

26. Ccg-270358

27. Ac-28750

28. As-57710

29. Bedaquiline Fumarate [orange Book]

30. D09873

31. R403323;tmc207 Fumarate;r207910 Fumarate

32. Q27139886

33. (1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol Bis[(2z)-but-2-enedioate]

34. (1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1- Phenylbutan-2-ol (2e)-but-2-enedioate Salt (1:1)

35. (1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol Fumarate

36. (1r,2s)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol;(e)-but-2-enedioic Acid

37. 3-quinolineethanol, 6-bromo-.alpha.-(2-(dimethylamino)ethyl)-2-methoxy-.alpha.-1-naphthalenyl-.beta.-phenyl-, (.alpha.s,.beta.r)-, (2e)-2-butenedioate (1:1) (salt)

38. 3-quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl- -phenyl-, (s,r)-, (2e)-2-butenedioate (1:1) (salt)

39. 6-bromo-3-[(1r,2s)-4-(dimethylammonio)-2-hydroxy-2-(1-naphthyl)-1-phenylbutyl]-2-methoxyquinolinium (2e)-but-2-enedioate

2.4 Create Date
2008-06-23
3 Chemical and Physical Properties
Molecular Weight 671.6 g/mol
Molecular Formula C36H35BrN2O6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count10
Exact Mass670.16785 g/mol
Monoisotopic Mass670.16785 g/mol
Topological Polar Surface Area120 Ų
Heavy Atom Count45
Formal Charge0
Complexity834
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Indication

Sirturo is indicated for use as part of an appropriate combination regimen for pulmonary multidrug resistant tuberculosis (MDR TB) in adults and adolescent patients (12 years to less than 18 years of age and weighing at least 30 kg) when an effective treatment regimen cannot otherwise be composed for reasons of resistance or tolerability. Consideration should be given to official guidance on the appropriate use of antibacterial agents.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antitubercular Agents

Drugs used in the treatment of tuberculosis. They are divided into two main classes: "first-line" agents, those with the greatest efficacy and acceptable degrees of toxicity used successfully in the great majority of cases; and "second-line" drugs used in drug-resistant cases or those in which some other patient-related condition has compromised the effectiveness of primary therapy. (See all compounds classified as Antitubercular Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Diarylquinolines [CS]; Diarylquinoline Antimycobacterial [EPC]
5.3 ATC Code

J04AK05


API SUPPLIERS

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01

Nuray Chemicals Private Limited

India

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Virtual BoothNuray is an expert in the synthesis of Niche novel APIs, the first to launch Generics, NCEs, Advanced Intermediates // USFDA certified.

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Omgene Life Sciences

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Virtual BoothOmgene: R&D-based biopharmaceutical company with GMP facilities, focused on innovation and high-quality, affordable medicines.

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Viatris

U.S.A

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Viatris

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MSN Laboratories

India

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MSN Laboratories

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Haoyuan Chemexpress Co.Ltd

China

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Arene Lifesciences

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Beijing Fukangren Biopharmaceutica...

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Epoch Labs

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Shanvr Life Sciences

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DEAFARMA

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04-Feb-2021
31-Aug-2024
KGS
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