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    Chemistry

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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 Reference Price

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    04-Feb-2021
    15-Oct-2024
    KGS
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