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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H69NO15
Molecular Weight 827.995
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of JOSAMYCIN

SMILES

CO[C@H]1[C@@H](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)OC(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
Molecular Formula C42H69NO15
Molecular Weight 827.995
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

Yamanouchi Pharmaceutical
31
Curator's Comment: Predecessor of Astellas Pharma Inc.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
 5.5 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
Josamycin

Approved Use

Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.
Curative
Approved
8583
Josamycin

Approved Use

Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.
Curative
Approved
8583
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
Patents

Patents

JPS60172993A
2
US3636197
2

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
Created
by admin
on Mon Mar 31 17:57:08 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:08 GMT 2025
Record UNII
HV13HFS217
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
JOSAMYCIN
EP   INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
JOSAMINA
Preferred 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
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 [WHO-DD]
Common Name English
josamycin [INN]
Common Name English
TURIMYCIN A5
Common Name English
LEUCOMYCIN V, 3-ACETATE 4B-(3-METHYLBUTANOATE)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C261
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
WHO-VATC QJ01FA07
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
WHO-ATC J01FA07
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
Code System Code Type Description
INN
2837
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
EVMPD
SUB12091MIG
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
MERCK INDEX
m6585
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
240-871-6
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
FDA UNII
HV13HFS217
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
MESH
D015570
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
PUBCHEM
5282165
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
NCI_THESAURUS
C83851
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
CAS
16846-24-5
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
CHEBI
31739
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
SMS_ID
100000079852
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
DRUG BANK
DB01321
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
WIKIPEDIA
Josamycin
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
RXCUI
6084
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL224436
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
DRUG CENTRAL
1518
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID8023183
Created by admin on Mon Mar 31 17:57:08 GMT 2025 , Edited by admin on Mon Mar 31 17:57:08 GMT 2025
PRIMARY
Related Record Type Details
Structure of LEUCOMYCIN A1
ACTIVE MOIETY
Structure of JOSAMYCIN
ACTIVE MOIETY
NIH
NCATS
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