U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C40H67NO14
Molecular Weight 785.9583
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEUCOMYCIN A1

SMILES

CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@@H]([C@H]2O)N(C)C

InChI

InChIKey=IEMDOFXTVAPVLX-YWQHLDGFSA-N
InChI=1S/C40H67NO14/c1-22(2)18-30(45)53-38-26(6)51-32(21-40(38,7)48)54-35-25(5)52-39(34(47)33(35)41(8)9)55-36-27(16-17-42)19-23(3)28(43)15-13-11-12-14-24(4)50-31(46)20-29(44)37(36)49-10/h11-13,15,17,22-29,32-39,43-44,47-48H,14,16,18-21H2,1-10H3/b12-11+,15-13+/t23-,24-,25-,26+,27+,28+,29-,32+,33-,34-,35-,36+,37+,38+,39+,40-/m1/s1

HIDE SMILES / InChI

Molecular Formula C40H67NO14
Molecular Weight 785.9583
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Josamycin is a macrolide antibiotic produced by Streptomyces narbonensis var. josamyceticus. Macrolides are inhibitors of protein synthesis. They impair the elongation cycle of the peptidyl chain by specifically binding to the 50S subunit of the ribosome. Josamycin has antimicrobial activity against a wide spectrum of pathogens. It is similar to erythromycin, but does not induce macrolide resistance in staphylococci and appears to have a lower incidence of gastrointestinal side effects. Josamycin is under investigation in US.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
5.5 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Josamycin
Curative
Josamycin
Curative
Josamycin

PubMed

Sample Use Guides

In Vivo Use Guide
Bronchitis: 500 mg three times daily for up to 14 days. Mediterranean spotted fever: 1 g every 8 hours for 5 days. Mycoplasma pneumonia: 2 g per day (in four equally divided doses) for 7 days.
Route of Administration: Oral
In Vitro Use Guide
The MIC values for josamycin were: 0.007-0.25 ug/ml (Mycoplasma pneumoniae), 0.007-0.25 ug/ml (Streptococcus pneumoniae), 0.06-0.5 ug/ml (Streptococcus pyogenes), 0.5-2.0 ug/ml (Staphylococcus aureus), 0.5-8.0 ug/ml (Haemophilus influenzae), 0.125->8 ug/ml (Bacteroides fiagilis).
Substance Class Chemical
Record UNII
YX09Z4QW5Y
Record Status Validated (UNII)
Record Version