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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H69NO15
Molecular Weight 827.9966
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of JOSAMYCIN

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)OC(=O)C)O

InChI

InChIKey=XJSFLOJWULLJQS-NGVXBBESSA-N
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

HIDE SMILES / InChI

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 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).
Name Type Language
JOSAMYCIN
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
IOSALIDE
Common Name English
LEUCOMYCIN A3
Common Name English
JOSAMYCIN [EP MONOGRAPH]
Common Name English
JOSAMYCIN [USAN]
Common Name English
LEUCOMYCIN V 3-ACETATE 4B-(3-METHYLBUTANOATE)
Common Name English
JOSAMYCIN [MI]
Common Name English
EN-141
Code English
JOMYBEL
Common Name English
KITASAMYCIN A3
Common Name English
JOSAMYCIN [WHO-DD]
Common Name English
LEUCOMYCIN V, 3-ACETATE 4(SUP .BETA.)-(3-METHYLBUTANOATE)
Common Name English
JOSAMYCIN [JAN]
Common Name English
JOSAMYCIN [MART.]
Common Name English
JOSAMYCINE
Common Name English
JOSAMYCIN [INN]
Common Name English
TURIMYCIN A5
Common Name English
LEUCOMYCIN V, 3-ACETATE 4B-(3-METHYLBUTANOATE)
Common Name English
JOSAMINA
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C261
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
WHO-VATC QJ01FA07
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
WHO-ATC J01FA07
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
Code System Code Type Description
INN
2837
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
EVMPD
SUB12091MIG
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
MERCK INDEX
M6585
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
240-871-6
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
FDA UNII
HV13HFS217
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
MESH
D015570
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
PUBCHEM
5282165
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
NCI_THESAURUS
C83851
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
CAS
16846-24-5
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
DRUG BANK
DB01321
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
RXCUI
6084
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL224436
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
DRUG CENTRAL
1518
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY
EPA CompTox
16846-24-5
Created by admin on Fri Jun 25 21:19:26 UTC 2021 , Edited by admin on Fri Jun 25 21:19:26 UTC 2021
PRIMARY