Josamycin

Josamycin is a macrolide antibiotic. It was isolated by Hamao Umezawa and his colleagues from strains of Streptomyces narbonensis var. josamyceticus var. nova in 1964.[1][2]

Josamycin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • (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)oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydro xy-2-methyltetrahydro-2H-pyran-3-yl]oxy}-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.037.140
Chemical and physical data
FormulaC42H69NO15
Molar mass828.006 g·mol−1
3D model (JSmol)
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
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 Y
  • Key:XJSFLOJWULLJQS-NGVXBBESSA-N Y
 NY (what is this?)  (verify)

It is currently sold in various countries.

Brand examples are:

  • Europe: Josalid, Josacine, Iosalide, Josamina
  • Russia: Wilprafen (Вильпрафен)
  • Japan: Josamy

Adverse effects

There has been a case report of edema of the feet.[3]

References
  1. Osono, T; Oka, Y; Watanabe, S; Okami, Y; Umezawa, H (1967). "A new antibiotic, josamycin. I. Isolation and physico-chemical characteristics". The Journal of Antibiotics, Series A. 20 (3): 174–180. PMID 6072798.
  2. Umezawa, H (1982). "Discovery of Josamycin". Giornale italiano di chemioterapia. 29 Supplement 1: 1–10. PMID 6765367.
  3. Bosch X, Pedrol E, Casado X, Urbano-Marquez A (July 1993). "Josamycin-induced pedal oedema". BMJ. 307 (6895): 26. doi:10.1136/bmj.307.6895.26-a. PMC 1678472. PMID 8343666.
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