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    Josamycin

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

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    $ API Ref.Price (USD/KG) : 474Xls

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    2D Structure
    Also known as: Leucomycin a3, Turimycin a5, Kitasamycin a3, Josamycine, Antibiotic yl-704 a3, 16846-24-5
    Molecular Formula
    C42H69NO15
    Molecular Weight
    828.0  g/mol
    InChI Key
    XJSFLOJWULLJQS-NGVXBBESSA-N
    FDA UNII
    HV13HFS217
    A macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
    2.1.2 InChI
    InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
    2.1.3 InChI Key
    XJSFLOJWULLJQS-NGVXBBESSA-N
    2.1.4 Canonical SMILES
    CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)OC(=O)C)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
    2.1.5 Isomeric SMILES
    C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    HV13HFS217
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. En 141

    2. En-141

    3. En141

    4. Josamycine

    5. Kitasamycin A3

    6. Leucomycin A3

    7. Turimycin A5

    8. Wilprafen

    2.3.2 Depositor-Supplied Synonyms

    1. Leucomycin A3

    2. Turimycin A5

    3. Kitasamycin A3

    4. Josamycine

    5. Antibiotic Yl-704 A3

    6. 16846-24-5

    7. Josamicina

    8. Josamycinum

    9. Josamycine [inn-french]

    10. Josamycinum [inn-latin]

    11. Iosalide

    12. Josamina

    13. Josamicina [inn-spanish]

    14. En-141

    15. Yl-704 A3

    16. Jomybel

    17. Josacine

    18. Leucomycin V 3-acetate 4b-(3-methylbutanoate)

    19. Leucomycin V, 3-acetate 4b-(3-methylbutanoate)

    20. Leucomycin V, 3-acetate 4(sup B)-(3-methylbutanoate)

    21. Hv13hfs217

    22. Leucomycin V, 3-acetate 4(sup Beta)-(3-methylbutanoate)

    23. Jm

    24. Chebi:31739

    25. Mfcd00210320

    26. En 141

    27. Einecs 240-871-6

    28. Unii-hv13hfs217

    29. Ccris 8511

    30. Nsc122223

    31. Hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate

    32. Josamycin [usan:inn:ban:jan]

    33. Josamycin (tn)

    34. [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-

    35. St075007

    36. Josamycin [inn]

    37. Josamycin [jan]

    38. Josamycin [mi]

    39. Josamycin [usan]

    40. Josamycin [mart.]

    41. Josamycin [who-dd]

    42. [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate

    43. Stereoisomer Of 4-(acetyloxy)-6-((3,6-dideoxy-4-o-(2,6-dideoxy-3-c-methyl-4-o-(3-methyl-1-oxobutyl)-alpha-l-ribo-hexopyranosyl)-3-(dimethylamino)-beta-d-glucopyranosyl)oxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-diene-7-acetaldehyde

    44. Stereoisomer Of 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-o-(2,6-dideoxy-3-c-methyl-alpha-l-ribo-hexopyranosyl)-3-(dimethylamino)-beta-d-glucopyranoside 4'-acetate 4''-isovalerate

    45. Schembl132829

    46. Leucomycin V 3-acetate 4(beta)-(3-methylbutanoate)

    47. Chembl224436

    48. Josamycin (jp17/usan/inn)

    49. Josamycin [ep Monograph]

    50. Josamycin, >=98.0% (uv)

    51. Hy-b1920

    52. S4421

    53. Zinc96006021

    54. Db01321

    55. Stereoisomer Of 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-o-(2,6-dideoxy-3-c-methyl-alpha-l-ribo-hexopyranosyl)-3-(dimethylamino)-beta-d-glucopyranoside 4'-acetate 4'-isovalerate

    56. Cs-0013975

    57. D01235

    58. Leucomycin V 3-acetate 4(b)-(3-methylbutanoate)

    59. Leucomycin V 3-acetate 4beta-(3-methylbutanoate)

    60. Q423369

    61. Sr-01000883731

    62. En-141;kitasamycin A3;leucomycin A3;turimycin A5

    63. Sr-01000883731-1

    64. Josamycin, European Pharmacopoeia (ep) Reference Standard

    65. Leucomycin V, 3-acetate 4(sup .beta.)-(3-methylbutanoate)

    66. Josamycin For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    67. (2s,3s,4r,6s)-6-{[(2r,3s,4r,5r,6s)-6-{[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate

    68. [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-4-acetoxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyl-tetrahydropyran-3-yl]oxy-4-hydroxy-2,4-dimethyl-tetrahydropyran-3-yl] 3-methylbutanoate

    69. 56689-45-3

    70. 6-{6-[3-acetyloxy-13-hydroxy-2-methoxy-7,14-dimethyl-6-oxa-5-oxo-16-(2-oxoethyl)cyclohexadeca-9,11-dienyloxy]-4-(dimethylamino)-5-hydroxy-2-methylperhydro-2h-pyran-3-yloxy}-4-hydroxy-2,4-dimethylperhydro-2h-pyran-3-yl 3-methylbutanoate

    71. Josamycin 10 Microg/ml In Acetonitrile. Short Expiry Date Due To Chemical Nature Of Component(s)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 828.0 g/mol
    Molecular Formula C42H69NO15
    XLogP32.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count14
    Exact Mass827.46672049 g/mol
    Monoisotopic Mass827.46672049 g/mol
    Topological Polar Surface Area206 Ų
    Heavy Atom Count58
    Formal Charge0
    Complexity1390
    Isotope Atom Count0
    Defined Atom Stereocenter Count16
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of bacterial infections.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Josamycin is a macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01F - Macrolides, lincosamides and streptogramins

    J01FA - Macrolides

    J01FA07 - Josamycin

    5.4 Mechanism of Action

    The mechanism of action of macrolides such as Josamycin is via inhibition of bacterial protein biosynthesis by binding reversibly to the subunit 50S of the bacterial ribosome, thereby inhibiting translocation of peptidyl tRNA. This action is mainly bacteriostatic, but can also be bactericidal in high concentrations. Macrolides tend to accumulate within leukocytes, and are therefore actually transported into the site of infection.