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    Chemistry

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    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
    Josamycin
    A macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens.
    1 2D Structure

    Josamycin

    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.

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    Certificate Number : CEP 2021-502 - Rev 01

    Issue Date : 2024-07-01

    Type : Chemical

    Substance Number : 1983

    Status : Valid

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    Registration Number : 217MF10599

    Registrant's Address : 1-3-1 Kyobashi, Chuo-ku, Tokyo

    Initial Date of Registration : 2005-09-14

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    Regulatory Info :

    Registration Country : Italy

    Josamycin

    Brand Name : Ialide

    Dosage Form : Josamycin 1.000Mg 12 Combined Oral Use

    Dosage Strength : 12 cpr dispers 1 g

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    Josamycin

    Brand Name : Ialide

    Dosage Form : Josamycin 500Mg 12 Combined Oral Use

    Dosage Strength : 12 cpr riv 500 mg

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    Josamycine

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    Dosage Strength : 250MG

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    Josamycin

    Dosage Form : Josamycin 1.000Mg 12 Combined Or...

    Dosage Strength : 12 cpr dispers 1 g

    Price Per Pack (Euro) : 13.59

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    Josamycin (15 MT -20 MT) API needed in India [ENA20019]
    A global pharmaceutical company that focuses on research, development & manufacturing of a wide range of products in various therapeutic segments like pain, CNS, cardiovascular, diabetes and gastroenterology is looking for suppliers of Josamycin (15 MT -20 MT) API for commercial purposes. The suppliers must support this enquiry with CEP & CoA.
    18 Jul 2024

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    18 Jul 2024

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    Josamycin Propionate (2 kg) API needed in Uzbekistan [ENA19666]
    A company focusing on manufacturing of various finished dosage formulations & nutraceuticals is looking for suppliers of Ph. Eur./ BP/ USP Grade Josamycin Propionate (2 kg) API for commercial purposes. The suppliers must support this enquiry with DMF & CoA.
    08 Jun 2024

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    08 Jun 2024

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    Josamycin (100 kg) API needed in Algeria [ENA19257]
    A company specializing in the production of generic medications in solid dosage forms, including film-coated tablets, effervescent tablets and capsules is looking for suppliers of Josamycin (100 kg) API for development purposes. The suppliers must support this enquiry with GMP, DMF & CoA.
    28 Mar 2024

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    28 Mar 2024

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    Josamycin (1 MT/ year) API needed in Russia [ENA19223]
    A company that focuses on research, development & manufacturing of OSDs, oral suspensions, suppositories & syrups is looking for suppliers of Josamycin (1 MT/ year) API for commercial purposes. The suppliers must support this enquiry with ODMF, CEP & CoA.
    20 Mar 2024

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    20 Mar 2024

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    Josamycin API needed in Japan [ENA18846]
    A company based in China that focuses on manufacturing, import & export of chemical raw materials is looking for suppliers of Josamycin API for commercial purposes. The required annual commercial quantity is 3 MT. The suppliers must support this enquiry with DMF & CoA.
    02 Jan 2024

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    02 Jan 2024

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    EP Grade Josamycin (300 kg - 500 kg/ annum) API needed in Russia [ENA15131]
    A Russian pharmaceutical company that focuses on the production and development of antiseptic and disinfecting drugs is looking for suppliers of EP Grade Josamycin (300 kg - 500 kg/ annum) API for commercial purpose. The suppliers must support this enquiry with GMP.
    26 Sep 2022

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    26 Sep 2022

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    26 Sep 2022

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    Josamycin (250 kg) API needed in India [ENA13933]
    A company that focuses in manufacturing of various pharmaceutical products is looking for suppliers of Josamycin (250 kg) API for commercial purpose. The suppliers must support this enquiry with CoA.
    11 Jun 2022

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    11 Jun 2022

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    11 Jun 2022

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    Various APIs needed in India [ENA06470]
    A company that offers animal feed supplement products, quality solutions for Poultry, Veterinary and Shrimp (Aqua) industry is looking for various feed grade APIs for research purposes. The required quantity is MOQ for each API. 1. Kitasamycin 2. Monensin Sodium 3. Salinomycin Sodium
    04 Feb 2020

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    04 Feb 2020

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    04 Feb 2020

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    Josamycin Propionate API needed in Algeria [ENA05231]
    A research and development company offering variety in the service of healthcare professionals, in order to improve patient care is looking for suppliers of Josamycin Propionate API. The supplier must support this enquiry with DMF and GMP.
    21 Sep 2019

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    21 Sep 2019

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    21 Sep 2019

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    Josamycin (220 kg) and Amphotericin B (10 kg) APIs needed in India [ENA04524]
    A trading company offering services to major hospitals, academic institutions, research laboratories and manufacturing units is looking for suppliers of Josamycin (220 kg) and Amphotericin B (10 kg) APIs. Suppliers must support with CoA and GMP.
    01 Jul 2019

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    01 Jul 2019

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    01 Jul 2019

    Only 10 entries up to this point, click to access all click full view read-more
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