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
Structure for Josamycin (DB01321)
- 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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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism A50S ribosomal protein L4 inhibitorHaemophilus 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Josamycin Action Pathway Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Josamycin. Acetyldigitoxin The serum concentration of Acetyldigitoxin can be increased when it is combined with Josamycin. Alfentanil The serum concentration of Alfentanil can be increased when it is combined with Josamycin. Alprazolam The serum concentration of Alprazolam can be increased when it is combined with Josamycin. Aminophylline The metabolism of Aminophylline can be decreased when combined with Josamycin. Atorvastatin The risk or severity of adverse effects can be increased when Josamycin is combined with Atorvastatin. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Josamycin. Betamethasone The serum concentration of Betamethasone can be increased when it is combined with Josamycin. Bromocriptine The serum concentration of Bromocriptine can be increased when it is combined with Josamycin. Bromotheophylline The metabolism of Bromotheophylline can be decreased when combined with Josamycin. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
- 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]
- External Links
- Human Metabolome Database
- HMDB0015418
- KEGG Drug
- D01235
- KEGG Compound
- C12662
- PubChem Compound
- 5282165
- PubChem Substance
- 46505431
- ChemSpider
- 4445361
- 6084
- ChEBI
- 31739
- ChEMBL
- CHEMBL224436
- ZINC
- ZINC000096006021
- Therapeutic Targets Database
- DAP000887
- PharmGKB
- PA164749133
- Wikipedia
- Josamycin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Infants, Premature 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral Granule, for suspension Oral 1 G Granule, for suspension Oral 250 MG/5ML Tablet, coated Oral 500 MG Tablet, for suspension 1 G Tablet, for suspension 500 MG Tablet, orally disintegrating Oral 500 mg Solution Oral Tablet, film coated Oral Granule Granule, for suspension Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 131.5 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0535 mg/mL ALOGPS logP 3.47 ALOGPS logP 3.22 ChemAxon logS -4.2 ALOGPS pKa (Strongest Acidic) 12.71 ChemAxon pKa (Strongest Basic) 7.9 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 206.05 Å2 ChemAxon Rotatable Bond Count 14 ChemAxon Refractivity 211.03 m3·mol-1 ChemAxon Polarizability 87.66 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5235 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.6872 P-glycoprotein substrate Substrate 0.586 P-glycoprotein inhibitor I Inhibitor 0.901 P-glycoprotein inhibitor II Inhibitor 0.901 Renal organic cation transporter Non-inhibitor 0.9274 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.5659 CYP450 1A2 substrate Non-inhibitor 0.907 CYP450 2C9 inhibitor Non-inhibitor 0.917 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9118 CYP450 3A4 inhibitor Non-inhibitor 0.8953 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9564 Ames test Non AMES toxic 0.8389 Carcinogenicity Non-carcinogens 0.9287 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.8513 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.978 hERG inhibition (predictor II) Non-inhibitor 0.9424
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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