Josamycin

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Structural formula
Structure of Josamycin
General
Non-proprietary name Josamycin
other names

(2 S , 3 S , 4 R , 6 S ) -6 - {[(2 R , 3 S , 4 R , 5 R , 6 S ) -6 - {[(4 R , 5 S , 6 S , 7 R , 9 R , 10 R , 11 E , 13 E , 16 R ) -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-dimethyloxane-3- yl-3-methylbutanoate ( IUPAC )

Molecular formula C 42 H 69 NO 15
Brief description

white to slightly yellowish, slightly hygroscopic powder

External identifiers / databases
CAS number 16846-24-5
EC number 240-871-6
ECHA InfoCard 100.037.140
PubChem 5282165
ChemSpider 4445361
DrugBank DB01321
Wikidata Q423369
Drug information
ATC code

J01 FA07

Drug class

Macrolide antibiotics

properties
Molar mass 827.99 g · mol -1
Physical state

firmly

Melting point

130-133 ° C

solubility

very sparingly soluble in water, slightly soluble in dichloromethane and methanol , soluble in acetone

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

> 7000 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Josamycin is an antibiotic from the group of macrolides . It is obtained from strains of Streptomyces narbonensis var. Josamyceticus var. Nova or, alternatively, produced synthetically.

pharmacology

Josamycin works against gram-positive bacteria such as staphylococci and streptococci, as well as against mycoplasma , chlamydia and many anaerobic bacteria. Josamycin is also effective against a number of gram-negative bacteria such as Legionella , Haemophilus influenzae and Bordetella pertussis . In terms of its action profile, it is therefore similar to the structurally related erythromycin .

Individual evidence

  1. ↑ a b c d data sheet JOSAMYCIN CRS (PDF) at EDQM , accessed on January 24, 2010.
  2. ↑ Josamycin data sheet from Sigma-Aldrich , accessed on May 26, 2011 ( PDF ).
  3. ↑ K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 4.01, Josamycin. Loose-leaf collection, 20th delivery 2005, Wissenschaftliche Verlagsgesellschaft Stuttgart.

Trade names

Josalid (A), Josamy (J), Wilprafen (Вильпрафен, RUS)

Web links