JOSAMYCIN

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 Search

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

Molecular Formula	C42H69NO15
Molecular Weight	827.9966
Charge	0
Count

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

Description
Sources: http://www.antimicrobe.org/drugpopup/josamycin.htm
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 172 Target ID: CHEMBL2363135 Sources: http://www.antimicrobe.org/drugpopup/josamycin.htm	Binding Agent 996		5.5 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Bronchitis 50 Sources: http://www.antimicrobe.org/drugpopup/josamycin.htm	Curative	Approved 8043	Josamycin Approved Use Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.
Mediterranean spotted fever 2 Sources: http://www.antimicrobe.org/drugpopup/josamycin.htm	Curative	Approved 8043	Josamycin Approved Use Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.
Mycoplasma pneumonia 2 Sources: http://www.antimicrobe.org/drugpopup/josamycin.htm	Curative	Approved 8043	Josamycin Approved Use Bronchitis, Mediterranean spotted fever, Mycoplasma pneumonia.

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
In vitro activity of antimicrobial agents against mycobacteria.	1988	3150951
In vitro stimulation of polymorphonuclear cell adhesion by ribomunyl and antibiotic + ribomunyl combinations: effects on CD18, CD35 and CD16 expression.	1993 Feb	8096833
In vitro susceptibilities of rapidly growing mycobacteria to telithromycin (HMR 3647) and seven other antimicrobials.	2000 Jan	10602744
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy-aminoalkyl-alpha,beta-unsaturated derivatives of the macrolide antibiotic josamycin.	2010 Apr	20186698

Patents

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 `Fri Jun 25 21:19:26 UTC 2021` Edited by `admin` on `Fri Jun 25 21:19:26 UTC 2021`
Record UNII	HV13HFS217
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

JOSAMYCIN

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