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Josamycin

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ACTIVE PHARMA INGREDIENTS

6 API Suppliers, 1 CEP/COS, 1 JDMF, 6 Listed Suppliers, $ API Reference Price

6 API Suppliers
1 CEP/COS
1 JDMF
6 Listed Suppliers
$ API Reference Price

FINISHED DOSAGE FORMULATIONS

4 FDF Dossiers, 2 Europe, 2 Listed Dossiers

4 FDF Dossiers
2 Europe
2 Listed Dossiers

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2 Finished Drug Prices

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13 APIs, 4 FDF Dossiers

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13 APIs
4 FDF Dossiers

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1 EDQM

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1 EDQM

Athena Josamycin

Synopsis

ACTIVE PHARMA INGREDIENTS

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$ 474

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FDF

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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

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 Formula	C₄₂H₆₉NO₁₅
Molecular Weight	828.0 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	14
Exact Mass	827.46672049 g/mol
Monoisotopic Mass	827.46672049 g/mol
Topological Polar Surface Area	206 Å²
Heavy Atom Count	58
Formal Charge	0
Complexity	1390
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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