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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.


API SUPPLIERS

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Shanghai Minbiotech

China

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MicroBiopharm Japan

Japan

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MicroBiopharm Japan

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BrightGene Bio-Medical Technology ...

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Enomark

India

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Enomark

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Shandong Minglang Chemical

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Josamycin (JP)

Registration Number : 217MF10599

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

Initial Date of Registration : 2005-09-14

Latest Date of Registration : 2010-01-28

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Josamycin

About the Company : ​Headquartered in Fengxian District, Shanghai Minbiotch Co., Ltd. is a company specializing in the R&D and production of advanced pharmaceutical intermediates and biological APIs...

​Headquartered in Fengxian District, Shanghai Minbiotch Co., Ltd. is a company specializing in the R&D and production of advanced pharmaceutical intermediates and biological APIs. There are more than 1000 square meters of R&D centers in Nantong, Jiangsu and Jinan, Shandong, with more than 13,000㎡ of production sites. While supplying products to customers, the company also provides services such as technology development, technology transfer and technology exchange, aiming to provide customers with comprehensive supply and solutions in the biomedical industry.
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Josamycin

About the Company : BrightGene Bio-Medical Technology Co., Ltd. is a research driven biopharmaceutical company that engages in the R&D and manufacturing of innovative medicine as well as special gener...

BrightGene Bio-Medical Technology Co., Ltd. is a research driven biopharmaceutical company that engages in the R&D and manufacturing of innovative medicine as well as special generic APIs and FDFs with primary strategic focus on the regulated market. We have an exciting and very promising innovative pipeline including immuno-oncological therapeutic agents, orally available GLP-1RA peptides for type 2 diabetes, antibody drug conjugates for solid tumor, novel non-antibody dependent tumor targeting conjugates for brain cancer and solid tumor brain-metastasis.
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Enomark

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Enomark

India
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Josamycin

About the Company : ENOMARK Group of Companies stands as a prominent Contract Manufacturer, boasting a cutting-edge manufacturing facility in Ahmadabad (Gujarat) that complies with WHO-GMP standards. ...

ENOMARK Group of Companies stands as a prominent Contract Manufacturer, boasting a cutting-edge manufacturing facility in Ahmadabad (Gujarat) that complies with WHO-GMP standards. ENOMARK is known for its extensive product portfolio, which includes Tablets, Capsules, Dry Syrups, Protein Powders, Soft Gelatin Capsules, Gummy Candy, Liquid Orals, Oral Spray, Effervescent Tablets, Sachets and Oil.
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Josamycin

About the Company : MicroBiopharm Japan Co., Ltd. has introduced the products which we add the latest biotechnology to our fermentation technology fostered from our birth of business.In 1960´s we hav...

MicroBiopharm Japan Co., Ltd. has introduced the products which we add the latest biotechnology to our fermentation technology fostered from our birth of business.In 1960´s we have developed the antibiotics for agricultural use and for human and they are still now popular as long running products in the market.In 1970´s we have started the development of antitumor antibiotics and we have developed three antitumor antibiotics, manufactured and distributed them domestically and internationally. It comes to fruition.We have manufactured the above antitumor antibiotics by the chemical synthesis process in addition to fermentation process.
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Josamycin

About the Company : Minglang chemical is owned by Minglang Group, is a large manufacturer of fine chemical and cosmetic materials that integrates R&D, production and sales together. It is located in t...

Minglang chemical is owned by Minglang Group, is a large manufacturer of fine chemical and cosmetic materials that integrates R&D, production and sales together. It is located in the east of the Nanwang Economic Development District in Linzi, and the west of it is Qilu Petroleum Chemical Group, the east of it is Zijiang Road and the transportation is convenient. In recent years, the company has made a major breakthrough in food and feed additives, plant extraction, industrial chemicals industry.
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Josamycin

About the Company : With over a decade of experience in the Pharmaceutical and Health sector, HNB stands as a contemporary company specializing in the exploration, advancement, manufacturing, processi...

With over a decade of experience in the Pharmaceutical and Health sector, HNB stands as a contemporary company specializing in the exploration, advancement, manufacturing, processing, and global exportation of Active Pharmaceutical Ingredients (API), diverse additives encompassing those for food, feed, and cosmetics, a range of hormone products, and other related items since the year 2007.We pride ourselves on being your premier supplier, offering a wider array and the utmost quality in products. Our primary offerings include API, assorted additive products, and select Polypeptide Hormones.
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Europe

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Josamycin

Brand Name : Ialide

Dosage Form : Josamycin 1.000Mg 12 Combined Oral Use

Dosage Strength : 12 cpr dispers 1 g

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Registration Country : Italy

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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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Registration Country : Italy

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Dosage Form : Tablet

Dosage Strength : 500MG

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Finished Drug Prices

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Brand Name : Ialide

Japan
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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

Published in :

Country : Italy

RX/OTC/DISCN : Class A

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Josamycin

Dosage Form : Josamycin 500Mg 12 Combined Oral...

Dosage Strength : 12 cpr riv 500 mg

Price Per Pack (Euro) : 7.66

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Country : Italy

RX/OTC/DISCN : Class A

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EDQM

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Josamycin

CAS Number : 16846-24-5

Quantity Per Vial : 150 mg

Sale Unit : 1

Order Code : Y0000041

Batch No : 2

Price (€) : 79

Storage : -20°C ± 5°C

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