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Details

Stereochemistry ABSOLUTE
Molecular Formula C40H67NO14
Molecular Weight 785.9598
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEUCOMYCIN A1

SMILES

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

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 785.9598
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68015570 | https://www.ncbi.nlm.nih.gov/pubmed/4012

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

Curator's Comment:: Predecessor of Astellas Pharma Inc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.5 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Josamycin

Approved Use

Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.
Curative
Josamycin

Approved Use

Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.
Curative
Josamycin

Approved Use

Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
In vitro activity of antimicrobial agents against mycobacteria.
1988
In vitro stimulation of polymorphonuclear cell adhesion by ribomunyl and antibiotic + ribomunyl combinations: effects on CD18, CD35 and CD16 expression.
1993 Feb
In vitro susceptibilities of rapidly growing mycobacteria to telithromycin (HMR 3647) and seven other antimicrobials.
2000 Jan
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy-aminoalkyl-alpha,beta-unsaturated derivatives of the macrolide antibiotic josamycin.
2010 Apr
Patents

Sample Use Guides

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
Created
by admin
on Sat Jun 26 11:16:55 UTC 2021
Edited
by admin
on Sat Jun 26 11:16:55 UTC 2021
Record UNII
YX09Z4QW5Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEUCOMYCIN A1
MI  
Common Name English
3-O-DEACETYLJOSAMYCIN
Common Name English
3-DEACETYLJOSAMYCIN
Common Name English
TURIMYCIN H5
Common Name English
LEUCOMYCIN A1 [MI]
Common Name English
LEUCOMYCIN V, 4B-(3-METHYLBUTANOATE)
Common Name English
LEUCOMYCIN V 4-ISOVALERATE
Common Name English
KITASAMYCIN A1
Common Name English
Code System Code Type Description
MERCK INDEX
M6775
Created by admin on Sat Jun 26 11:16:55 UTC 2021 , Edited by admin on Sat Jun 26 11:16:55 UTC 2021
PRIMARY Merck Index
CAS
16846-34-7
Created by admin on Sat Jun 26 11:16:55 UTC 2021 , Edited by admin on Sat Jun 26 11:16:55 UTC 2021
PRIMARY
PUBCHEM
5282322
Created by admin on Sat Jun 26 11:16:55 UTC 2021 , Edited by admin on Sat Jun 26 11:16:55 UTC 2021
PRIMARY
FDA UNII
YX09Z4QW5Y
Created by admin on Sat Jun 26 11:16:55 UTC 2021 , Edited by admin on Sat Jun 26 11:16:55 UTC 2021
PRIMARY