NAV

Josamycin

Identification

Summary

Josamycin is a macrolide antibiotic used for the treatment of various susceptible bacterial infections.

Generic Name
Josamycin
DrugBank Accession Number
DB01321
Background

A macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 827.995
Monoisotopic: 827.466720543
Chemical Formula
C42H69NO15
Synonyms
  • JM
  • Josamicina
  • Josamycin
  • Josamycine
  • Josamycinum
  • Kitasamycin A3
  • Leucomycin A3
  • leucomycin V 3-acetate 4B-(3-methylbutanoate)
  • leucomycin V 3-acetate 4β-(3-methylbutanoate)
  • Turimycin A5
External IDs
  • Antibiotic yl-704 A3
  • EN-141
  • Yl-704 A3

Pharmacology

Indication

For the treatment of bacterial infections.

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Josamycin is a macrolide antibiotic from Streptomyces narbonensis. The drug has antimicrobial activity against a wide spectrum of pathogens.

Mechanism of action

The mechanism of action of macrolides such as Josamycin is via inhibition of bacterial protein biosynthesis by binding reversibly to the subunit 50S of the bacterial ribosome, thereby inhibiting translocation of peptidyl tRNA. This action is mainly bacteriostatic, but can also be bactericidal in high concentrations. Macrolides tend to accumulate within leukocytes, and are therefore actually transported into the site of infection.

TargetActionsOrganism
A50S ribosomal protein L4
inhibitor
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Josamycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Josamycin.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Josamycin.
AlfentanilThe serum concentration of Alfentanil can be increased when it is combined with Josamycin.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Josamycin.
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Josamycin.
ArticaineThe risk or severity of methemoglobinemia can be increased when Josamycin is combined with Articaine.
AtorvastatinThe risk or severity of adverse effects can be increased when Josamycin is combined with Atorvastatin.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Josamycin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Josamycin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Josamycin is combined with Benzyl alcohol.
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Food Interactions
Not Available

Products

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International/Other Brands
Josacine / Josalid / Josamy

Categories

ATC Codes
J01FA07 — Josamycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Macrolides and analogues / Disaccharides / O-glycosyl compounds / Tricarboxylic acids and derivatives / Fatty acid esters / Oxanes / Tertiary alcohols / Alpha-hydrogen aldehydes / 1,2-aminoalcohols / Secondary alcohols
show 10 more
Substituents
1,2-aminoalcohol / Acetal / Alcohol / Aldehyde / Aliphatic heteromonocyclic compound / Alpha-hydrogen aldehyde / Amine / Amino acid or derivatives / Aminoglycoside core / Carbonyl group
show 24 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
tertiary alcohol, tertiary amino compound, macrolide antibiotic, acetate ester, disaccharide derivative, glycoside, aldehyde (CHEBI:31739)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
HV13HFS217
CAS number
16846-24-5
InChI Key
XJSFLOJWULLJQS-NGVXBBESSA-N
InChI
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
IUPAC Name
(2S,3S,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy}-4-hydroxy-2,4-dimethyloxan-3-yl 3-methylbutanoate
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]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O2)[C@@H]([C@H]1O)N(C)C)OC(C)=O

References

Synthesis Reference

Takashi Osono, Kiruko Moriyama, Keisuke Murakami, Hamao Umezawa, "Process for the production of monopropionyl-josamycin-2." U.S. Patent US4001399, issued January, 1972.

US4001399
General References
  1. Przybylski P, Pyta K, Stefanska J, Brzezinski B, Bartl F: Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy-aminoalkyl-alpha,beta-unsaturated derivatives of the macrolide antibiotic josamycin. Magn Reson Chem. 2010 Apr;48(4):286-96. doi: 10.1002/mrc.2574. [Article]
Human Metabolome Database
HMDB0015418
KEGG Drug
D01235
KEGG Compound
C12662
PubChem Compound
5282165
PubChem Substance
46505431
ChemSpider
4445361
RxNav
6084
ChEBI
31739
ChEMBL
CHEMBL224436
ZINC
ZINC000096006021
Therapeutic Targets Database
DAP000887
PharmGKB
PA164749133
Wikipedia
Josamycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentInfants, Premature1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral
Granule, for suspensionOral1 G
Granule, for suspensionOral250 MG/5ML
Tablet, coatedOral500 MG
Tablet, for suspension1 G
Tablet, for suspension500 MG
Tablet, orally disintegratingOral500 mg
SolutionOral
Tablet, film coatedOral
Granule
Granule, for suspensionOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)131.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0535 mg/mLALOGPS
logP3.47ALOGPS
logP3.22Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.71Chemaxon
pKa (Strongest Basic)7.9Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count13Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area206.05 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity211.03 m3·mol-1Chemaxon
Polarizability87.66 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5235
Blood Brain Barrier-0.9659
Caco-2 permeable-0.6872
P-glycoprotein substrateSubstrate0.586
P-glycoprotein inhibitor IInhibitor0.901
P-glycoprotein inhibitor IIInhibitor0.901
Renal organic cation transporterNon-inhibitor0.9274
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5659
CYP450 1A2 substrateNon-inhibitor0.907
CYP450 2C9 inhibitorNon-inhibitor0.917
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9118
CYP450 3A4 inhibitorNon-inhibitor0.8953
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9564
Ames testNon AMES toxic0.8389
CarcinogenicityNon-carcinogens0.9287
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8513 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.978
hERG inhibition (predictor II)Non-inhibitor0.9424
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. 50S ribosomal protein L4
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Structural constituent of ribosome
Specific Function
One of the primary rRNA binding proteins, this protein initially binds near the 5'-end of the 23S rRNA. It is important during the early stages of 50S assembly. It makes multiple contacts with diff...
Gene Name
rplD
Uniprot ID
P44345
Uniprot Name
50S ribosomal protein L4
Molecular Weight
21954.185 Da
References
  1. Tait-Kamradt A, Davies T, Cronan M, Jacobs MR, Appelbaum PC, Sutcliffe J: Mutations in 23S rRNA and ribosomal protein L4 account for resistance in pneumococcal strains selected in vitro by macrolide passage. Antimicrob Agents Chemother. 2000 Aug;44(8):2118-25. [Article]

Drug created at June 30, 2007 17:19 / Updated at June 12, 2021 10:52