Josamycin

Josamycin

Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	16846-24-5
ATC code	J01FA07 (WHO)
PubChem	CID 5284579
DrugBank	DB01321
ChemSpider	4447629
UNII	HV13HFS217
KEGG	D01235
ChEBI	CHEBI:31739
ChEMBL	CHEMBL224436
PDB ligand ID	JOS (PDBe, RCSB PDB)
Chemical data
Formula	C42H69NO15
Molar mass	827.995 g/mol
SMILES O=CC[C@H]3C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@H](OC(=O)C[C@@H](OC(=O)C)C(OC)[C@H]3O[C@@H]2O[C@@H]([C@@H](O[C@@H]1O[C@H]([C@@H](OC(=O)CC(C)C)[C@](O)(C1)C)C)[C@H](N(C)C)[C@H]2O)C)C
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 Key:XJSFLOJWULLJQS-HTYUZQQASA-N
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Josamycin is a macrolide antibiotic. It is synthesized from strains of Streptomyces narbonensis var. josamyceticus var. nova

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 oedema of the feet.^[1]

References

1. Bosch, X.; Pedrol, E.; Casado, X.; Urbano-Marquez, A. (1993). "Josamycin-induced pedal oedema" (pdf). British Medical Journal (Clinical research ed.) 307 (6895): 26. doi:10.1136/bmj.307.6895.26-a. PMC 1678472. PMID 8343666.