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MedKoo Cat#: 341150 | Name: Josamycin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Josamycin is a macrolide antibiotic. It was isolated by Hamao Umezawa and his colleagues from strains of Streptomyces narbonensis var. josamyceticus var. nova in 1964. Josamycin inhibits bacterial protein biosynthesis by inhibiting peptidyltransferase and ribosomal translocation, and depleting the intracellular pools of aminoacyl-tRNAs available for protein synthesis by drop-off and incomplete peptidyl-tRNA hydrolase activity. It slows down formation of the first peptide bond of a nascent peptide in an amino acid-dependent way and inhibits formation of the second or third peptide bond.

Chemical Structure

Josamycin
Josamycin
CAS#16846-24-5

Theoretical Analysis

MedKoo Cat#: 341150

Name: Josamycin

CAS#: 16846-24-5

Chemical Formula: C42H69NO15

Exact Mass: 827.4667

Molecular Weight: 828.01

Elemental Analysis: C, 60.92; H, 8.40; N, 1.69; O, 28.98

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
200mg USD 450.00 2 Weeks
500mg USD 750.00 2 Weeks
1g USD 1,250.00 2 Weeks
2g USD 2,150.00 2 Weeks
5g USD 4,250.00 2 Weeks
10g USD 7,650.00 2 Weeks
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Synonym
Josamycin; Leucomycin A3;
IUPAC/Chemical Name
Leucomycin V, 3-acetate 4(sup B)-(3-methylbutanoate)
InChi Key
XJSFLOJWULLJQS-DJBGMQKKSA-N
InChi Code
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
SMILES Code
O([C@@H]1[C@H]([C@@H](CC(O[C@@H](CC=CC=C[C@@H]([C@@H](C[C@@H]1CC=O)C)O)C)=O)OC(C)=O)OC)[C@H]1[C@@H]([C@H]([C@H](O[C@H]2C[C@@]([C@@H](OC(CC(C)C)=O)[C@@H](O2)C)(C)O)[C@H](O1)C)N(C)C)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Josamycin (EN-141) is a macrolide antibiotic exhibiting antimicrobial activity against a wide spectrum of pathogens, such as bacteria.
In vitro activity:
Josamycin slows down formation of the first peptide bond of a nascent peptide in an amino acid-dependent way and completely inhibits formation of the second or third peptide bond, depending on peptide sequence. Erythromycin allows formation of longer peptide chains before the onset of inhibition. Both drugs stimulate the rate constants for drop-off of peptidyl-tRNA from the ribosome. In the josamycin case, drop-off is much faster than drug dissociation, whereas these rate constants are comparable in the erythromycin case. Therefore, at a saturating drug concentration, synthesis of full-length proteins is completely shut down by josamycin but not by erythromycin. Reference: J Biol Chem. 2004 Dec 17;279(51):53506-15. https://pubmed.ncbi.nlm.nih.gov/15385552/
In vivo activity:
Josamycin (0.1%) was topically administered to NC/Nga mice with AD-like skin lesions induced by a mite antigen, Dermatophagoides farinae extract, and the therapeutic effects of josamycin were assessed by measurement of the skin severity score, S. aureus colonization, scratching count, and interleukin (IL)-31 mRNA expression in the skin lesions. Topical treatment with josamycin ointment significantly suppressed the increase of the skin severity score in NC/Nga mice. Reference: Biol Pharm Bull. 2021;44(6):798-803. https://pubmed.ncbi.nlm.nih.gov/34078811/
Solvent mg/mL mM
Solubility
DMF 25.0 30.19
DMSO 28.3 34.22
Ethanol 25.0 30.19
Ethanol:PBS (pH 7.2) (1:2) 0.3 0.36
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 828.01 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lovmar M, Tenson T, Ehrenberg M. Kinetics of macrolide action: the josamycin and erythromycin cases. J Biol Chem. 2004 Dec 17;279(51):53506-15. doi: 10.1074/jbc.M401625200. Epub 2004 Sep 22. PMID: 15385552. 2. Matsui K, Nakamura M, Obana N. Effects of Josamycin on Scratching Behavior in NC/Nga Mice with Atopic Dermatitis-Like Skin Lesions. Biol Pharm Bull. 2021;44(6):798-803. doi: 10.1248/bpb.b20-00976. PMID: 34078811. 3. Matsui K, Tachioka K, Onodera K, Ikeda R. Topical Application of Josamycin Inhibits Development of Atopic Dermatitis-Like Skin Lesions in NC/Nga Mice. J Pharm Pharm Sci. 2017;20:38-47. doi: 10.18433/J3GW3D. PMID: 28459659.
In vitro protocol:
1. Lovmar M, Tenson T, Ehrenberg M. Kinetics of macrolide action: the josamycin and erythromycin cases. J Biol Chem. 2004 Dec 17;279(51):53506-15. doi: 10.1074/jbc.M401625200. Epub 2004 Sep 22. PMID: 15385552.
In vivo protocol:
1. Matsui K, Nakamura M, Obana N. Effects of Josamycin on Scratching Behavior in NC/Nga Mice with Atopic Dermatitis-Like Skin Lesions. Biol Pharm Bull. 2021;44(6):798-803. doi: 10.1248/bpb.b20-00976. PMID: 34078811. 2. Matsui K, Tachioka K, Onodera K, Ikeda R. Topical Application of Josamycin Inhibits Development of Atopic Dermatitis-Like Skin Lesions in NC/Nga Mice. J Pharm Pharm Sci. 2017;20:38-47. doi: 10.18433/J3GW3D. PMID: 28459659.
1: Matsui K, Muranaka M, Yamaguchi T, Maeda M. Combination Therapy with Betamethasone and Josamycin Demonstrates Superior Therapeutic Efficacy in an NC/Nga Mouse Model of Atopic Dermatitis. Biol Pharm Bull. 2023;46(5):693-699. doi: 10.1248/bpb.b22-00781. PMID: 37121695. 2: Matsui K, Nakamura M, Obana N. Effects of Josamycin on Scratching Behavior in NC/Nga Mice with Atopic Dermatitis-Like Skin Lesions. Biol Pharm Bull. 2021;44(6):798-803. doi: 10.1248/bpb.b20-00976. PMID: 34078811. 3: Liu G, Zhu B, Ren X, Wang J. Universal response method for the quantitative analysis of multi-components in josamycin and midecamycin using liquid chromatography coupled with charged aerosol detector. J Pharm Biomed Anal. 2021 Jan 5;192:113679. doi: 10.1016/j.jpba.2020.113679. Epub 2020 Oct 13. PMID: 33120309. 4: Han J, Jin W, Wu Z, Shi Y, Cui F. Analysis of josamycin in three kinds of feed using ultra high performance liquid chromatography with tandem mass spectrometry. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2019 Sep;36(9):1302-1313. doi: 10.1080/19440049.2019.1628357. Epub 2019 Jun 26. PMID: 31241416. 5: Liu G, Xu Y, Sang J, Zhu B, Wang J. Characterization of a new component and impurities in josamycin by trap-free two-dimensional liquid chromatography coupled to ion trap time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2019 Jun 30;33(12):1058-1066. doi: 10.1002/rcm.8439. PMID: 30907019. 6: Choi EY, Choe SH, Hyeon JY, Park HR, Choi IS, Kim SJ. Josamycin suppresses Prevotella intermedia lipopolysaccharide-induced production of nitric oxide and interleukin-1β in murine macrophages. Biomed Pharmacother. 2018 Sep;105:498-505. doi: 10.1016/j.biopha.2018.05.139. Epub 2018 Jun 5. PMID: 29883945. 7: Matsui K, Tachioka K, Onodera K, Ikeda R. Topical Application of Josamycin Inhibits Development of Atopic Dermatitis-Like Skin Lesions in NC/Nga Mice. J Pharm Pharm Sci. 2017;20:38-47. doi: 10.18433/J3GW3D. PMID: 28459659. 8: Zhao ZH, Jin LL, Xu YP, Liu C, Wang AP, Lei PS. Synthesis and antibacterial activities of some novel 17, 18-unsaturated carbonyl compounds derivated from josamycin. J Asian Nat Prod Res. 2017 Apr;19(4):358-387. doi: 10.1080/10286020.2016.1194834. Epub 2016 Sep 26. PMID: 28276768. 9: Berthe-Aucejo A, Girard D, Lorrot M, Bellettre X, Faye A, Mercier JC, Brion F, Bourdon O, Prot-Labarthe S. Evaluation of frequency of paediatric oral liquid medication dosing errors by caregivers: amoxicillin and josamycin. Arch Dis Child. 2016 Apr;101(4):359-64. doi: 10.1136/archdischild-2015-309426. Epub 2016 Jan 4. PMID: 26729746. 10: Tamura H, Yamada A, Kato H. Identification of A2059G 23S rRNA and G439A rplC gene mutations in Streptococcus criceti strain OMZ 61, a strain resistant to azithromycin, josamycin and clindamycin. Genes Genet Syst. 2015;90(5):259-67. doi: 10.1266/ggs.15-00038. Epub 2015 Dec 25. PMID: 26725523. 11: Vinarov AZ, Stojlov SV, Kozyrev SV, Surikov VN, Chaban AV, Kurbatov DG, Shpilenja ES, Nejmark AI. [DOXYCYCLINE (UNIDOX SOLUTAB®) AND/OR JOSAMYCIN (WILPRAFEN®) IN TREATMENT OF PATIENTS WITH PROSTATITIS IN REAL CLINICAL PRACTICE. RESULTS OF THE TAURUS OBSERVATIONAL PROGRAM]. Urologiia. 2015 May- Jun;(3):75-8, 80-3. Russian. PMID: 26390565. 12: Auzou M, Caillon J, Poyart C, Weber P, Ploy MC, Leclercq R, Cattoir V. In vitro activity of josamycin against Streptococcus pyogenes isolated from patients with upper respiratory tract infections in France. Med Mal Infect. 2015 Jul;45(7):293-6. doi: 10.1016/j.medmal.2015.04.009. Epub 2015 Jun 6. PMID: 26055628. 13: Guschin A, Ryzhikh P, Rumyantseva T, Gomberg M, Unemo M. Treatment efficacy, treatment failures and selection of macrolide resistance in patients with high load of Mycoplasma genitalium during treatment of male urethritis with josamycin. BMC Infect Dis. 2015 Feb 3;15:40. doi: 10.1186/s12879-015-0781-7. PMID: 25645440; PMCID: PMC4318211. 14: Nasr JJ, Shalan S, Belal F. Simultaneous determination of tylosin and josamycin residues in muscles, liver, eggs and milk by MLC with a monolithic column and time-programmed UV detection: application to baby food and formulae. Chem Cent J. 2014 Jun 20;8:37. doi: 10.1186/1752-153X-8-37. PMID: 24976860; PMCID: PMC4069345. 15: Zhao Z, Jin L, Xu Y, Zhu D, Liu Y, Liu C, Lei P. Synthesis and antibacterial activity of a series of novel 9-O-acetyl- 4'-substituted 16-membered macrolides derived from josamycin. Bioorg Med Chem Lett. 2014 Jan 15;24(2):480-4. doi: 10.1016/j.bmcl.2013.12.029. Epub 2013 Dec 15. PMID: 24374276. 16: Van den Bossche L, Daidone F, Van Schepdael A, Hoogmartens J, Adams E. Characterization of impurities in josamycin using dual liquid chromatography combined with mass spectrometry. J Pharm Biomed Anal. 2013 Jan 25;73:66-76. doi: 10.1016/j.jpba.2012.01.012. Epub 2012 Jan 18. PMID: 22326844. 17: Przybylski P, Pyta K, Stefańska 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. PMID: 20186698. 18: Przybylski P, Pyta K, Brzezinski B. Fragmentation pathways of new aza derivatives of 16-membered macrolide antibiotic--analog of Josamycin investigated by ESI and FAB mass spectrometric methods. J Mass Spectrom. 2009 Sep;44(9):1395-401. doi: 10.1002/jms.1612. PMID: 19569070. 19: Lovmar M, Vimberg V, Lukk E, Nilsson K, Tenson T, Ehrenberg M. Cis-acting resistance peptides reveal dual ribosome inhibitory action of the macrolide josamycin. Biochimie. 2009 Aug;91(8):989-95. doi: 10.1016/j.biochi.2009.05.002. Epub 2009 May 20. PMID: 19463886. 20: Khrianin AA, Reshetnikov OV. [Is it safe to use josamycin in the obstetrics practice in Russia?]. Antibiot Khimioter. 2007;52(7-8):32-6. Russian. PMID: 18986022.