Josamycin

• CAS: 16846-24-5
• Catalog Number: ACM16846245
• Category: Main Products
• Molecular Weight: 827.99
• Molecular Formula: C42H69NO15
• Description: A 16-membered ring macrolide antibiotic with antimicrobial activity against a wide range of pathogens. Particularly used in the treatment of Mycoplasma infection.
• Synonyms: Iosalide;Vilprafen;Leucomycin A3;EN 141
• IUPAC Name: josamycin
• Boiling Point: 877.8ºC at 760mmHg
• Melting Point: 131.5°C
• Flash Point: 484.7ºC
• Density: 1.2 g/cm³
• Appearance: light yellow powder
• EC Number: 240-871-6
• Exact Mass: 827.46700
• LogP: 3.01340
• MDL Number: MFCD00211043
• PSA: 26.5
• Refractive Index: 1.534
• Storage Conditions: 2-8ºC
• WGK Germany: 2

Case Study

Josamycin Is Used as an Immunomodulatory Agent for Periodontal Disease Treatment

Choi E-Y, et al. Biomedicine & Pharmacotherapy, 2018, 105, 498-505.

Josamycin, a macrolide antibiotic, exhibits immunomodulatory properties that extend beyond its antibacterial activity. In a study investigating its effects on proinflammatory mediators in murine macrophages stimulated by lipopolysaccharide (LPS) from Prevotella intermedia, a pathogen linked to periodontal disease, josamycin demonstrated significant immunosuppressive potential. It reduced nitric oxide (NO) production by attenuating inducible nitric oxide synthase (iNOS) protein and mRNA expression. Although josamycin suppressed interleukin (IL)-1β release from LPS-stimulated cells, it did not affect IL-1β mRNA expression, mRNA stability, or intracellular IL-1β expression.
Mechanistically, josamycin enhanced heme oxygenase-1 (HO-1) induction, and its suppressive effect on NO generation was reversed by SnPP, an HO-1 activity inhibitor. Furthermore, josamycin diminished NF-κB transcriptional activity and upregulated SOCS1 mRNA levels, contributing to its anti-inflammatory effects. These findings highlight josamycin's ability to inhibit key inflammatory pathways, such as NF-κB activation, while promoting HO-1 and SOCS1 induction.

Josamycin Is Used for the Synthesis of 4'-Substituted Derivatives with Immunomodulatory and Anti-Inflammatory Applications

Zhao Z, et al. Bioorganic & Medicinal Chemistry Letters, 2014, 24(2), 480-484.

Josamycin serves as a versatile macrolide antibiotic that not only exhibits potent antibacterial and immunomodulatory properties but also acts as a critical precursor for synthesizing novel derivatives with enhanced therapeutic potential. A streamlined synthetic route for 4'-substituted josamycin derivatives was developed by removing the mycarose sugar and selectively modifying the 4'-hydroxyl group. This process involves acetylation of josamycin with acetic anhydride in pyridine, yielding a high-purity intermediate. Subsequent hydrolysis of the mycarose group and deprotection of the 2'-hydroxyl group using p-toluenesulfonic acid in toluene and methanol, respectively, produced a key intermediate (9-O-acetyl-desmycarosyl josamycin).

Custom Q&A

What is the molecular formula of Josamycin?

The molecular formula of Josamycin is C42H69NO15.

What are some synonyms for Josamycin?

Some synonyms for Josamycin include josamycine, Leucomycin A3, and Kitasamycin A3.

What is the chemical safety information for Josamycin?

The reference does not provide specific chemical safety information for Josamycin.

What is the chemical structure of Josamycin?

The chemical structure of Josamycin is not described in the reference.

What is the CAS number for Josamycin?

The CAS number for Josamycin is 16846-24-5.

What is the stereochemistry of Josamycin?

The reference mentions the stereochemistry of Josamycin, but does not provide specific details.

What is the pharmacological classification of Josamycin?

The reference does not mention the pharmacological classification of Josamycin.

What are the uses of Josamycin?

The reference does not describe the uses of Josamycin.

Is Josamycin available as a reference standard?

Yes, the reference mentions that there is a Josamycin reference standard available.

Are there any chemical derivatives or analogs of Josamycin?

The reference does not mention any chemical derivatives or analogs of Josamycin.