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MedKoo Cat#: 596283 | Name: Josamycin propionate

Description:

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

Josamycin propionate is a macrolide antibiotic. It is synthesized from strains of Streptomyces narbonensis var. josamyceticus var. nova

Chemical Structure

Josamycin propionate
Josamycin propionate
CAS#31674-19-8

Theoretical Analysis

MedKoo Cat#: 596283

Name: Josamycin propionate

CAS#: 31674-19-8

Chemical Formula: C45H73NO16

Exact Mass: 883.4929

Molecular Weight: 884.07

Elemental Analysis: C, 61.14; H, 8.32; N, 1.58; O, 28.96

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Synonym
Josamycin propionate; BRN 1677122; BRN-1677122; BRN1677122;
IUPAC/Chemical Name
(2S,3S,4R,6S)-6-(((2R,3S,4S,5R,6S)-6-(((4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetoxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-6-yl)oxy)-4-(dimethylamino)-2-methyl-5-(propionyloxy)tetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate
InChi Key
NBWASFCRCRXRKF-VGOAISAMSA-N
InChi Code
InChI=1S/C45H73NO16/c1-13-34(50)59-42-38(46(10)11)39(61-37-24-45(9,53)43(29(7)56-37)60-35(51)21-25(2)3)28(6)57-44(42)62-40-31(19-20-47)22-26(4)32(49)18-16-14-15-17-27(5)55-36(52)23-33(41(40)54-12)58-30(8)48/h14-16,18,20,25-29,31-33,37-44,49,53H,13,17,19,21-24H2,1-12H3/b15-14+,18-16+/t26-,27-,28-,29+,31+,32+,33-,37+,38+,39-,40+,41+,42-,43+,44+,45-/m1/s1
SMILES Code
CCC(O[C@@H]1[C@@H](N(C)C)[C@H](O[C@H]2C[C@@](C)(O)[C@@H](OC(CC(C)C)=O)[C@H](C)O2)[C@@H](C)O[C@H]1O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@@H](O)/C=C/C=C/C[C@@H](C)OC(C[C@@H](OC(C)=O)[C@@H]3OC)=O)=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/

Preparing Stock Solutions

The following data is based on the product molecular weight 884.07 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: Zhang X, Li J, Wang C, Song D, Hu C. Identification of impurities in macrolides by liquid chromatography-mass spectrometric detection and prediction of retention times of impurities by constructing quantitative structure- retention relationship (QSRR). J Pharm Biomed Anal. 2017 Oct 25;145:262-272. doi: 10.1016/j.jpba.2017.06.069. Epub 2017 Jul 6. PMID: 28700970. 2: Govaerts C, Chepkwony HK, Van Schepdael A, Adams E, Roets E, Hoogmartens J. Application of liquid chromatography-ion trap mass spectrometry to the characterization of the 16-membered ring macrolide josamycin propionate. J Mass Spectrom. 2004 Apr;39(4):437-46. doi: 10.1002/jms.612. PMID: 15103658. 3: Van Hoogdalem EJ, Terpstra IJ, Krauwinkel WJ, Volkers-Kamermans NJ, Baven AL, Verschoor JS. Multiple dose bioequivalence study with josamycin propionate, a drug with highly variable kinetics, in healthy volunteers. Int J Clin Pharmacol Ther. 1996 May;34(5):202-7. PMID: 8738856. 4: Ducci M, Scalori V. A rapid and sensitive high-pressure liquid chromatographic method for monitoring josamycin levels in plasma. Int J Clin Pharmacol Res. 1984;4(3):195-9. PMID: 6490238. 5: Privitera G, Bonino S, Del Mastro S. Clinical multicentre trial with josamycin propionate in paediatric patients. Int J Clin Pharmacol Res. 1984;4(3):201-7. PMID: 6386705. 6: Tachibana A, Sasaki H, Watanabe T, Yano K, Sado T. [Absorption, distribution and excretion of 14C-josamycin and 14C-josamycin propionate in rats (author's transl)]. Jpn J Antibiot. 1975 Aug;28(4):558-66. Japanese. PMID: 1160146. 7: Takagi T, Nozaki Y, Tachikawa S, Usuda S. [Studies on josamycin propionate. VIII. Further pharmacological studies (author's transl)]. Jpn J Antibiot. 1974 Aug;27(4):539-48. Japanese. PMID: 4474419. 8: Tachibana A, Komiya M, Sado T, Yano K. [Studies on josamycin propionate. VII. Prolonged oral administration in dogs (author's transl)]. Jpn J Antibiot. 1974 Aug;27(4):532-8. Japanese. PMID: 4436959. 9: Nakamizo Y, Akiba T, Tomizawa I, Tsuji M, Sato M. [A double-blind comparison of josamycin propionate and erythromycin ethylsuccinate in the treatment of scarlet fever with their oral suspension preparations (author's transl)]. Jpn J Antibiot. 1974 Apr;27(2):73-85. Japanese. PMID: 4603299. 10: Kobayashi Y, Akaishi K, Nishio T, Aihara M. [Josamycin propionate in the treatment of acute respiratory infections in children]. Jpn J Antibiot. 1973 Jun;26(3):267-76. Japanese. PMID: 4542549. 11: Oshima T, Iwadare M. [Josamycin propionate. 5. Teratological studies]. Jpn J Antibiot. 1973 Apr;26(2):148-53. Japanese. PMID: 4542540. 12: Hazato H, Yamamoto T, Tadokoro I, Kawamura A, Suzuki K. [Josamycin propionate. 4. Toxicity]. Jpn J Antibiot. 1973 Apr;26(2):136-47. Japanese. PMID: 4542539. 13: Tachibana A, Shibata M, Kumagai F, Moriyama K, Yano K. [Josamycin propionate. 2. Distribution and metabolism]. Jpn J Antibiot. 1973 Apr;26(2):122-9. Japanese. PMID: 4542538. 14: Osono T, Yano K, Murakami K, Miyamoto F, Murakami K. [Josamycin propionate. 1. Physicochemical and biological properties]. Jpn J Antibiot. 1973 Apr;26(2):115-21. Japanese. PMID: 4542537. 15: Takagi T. [Josamycin propionate. 3. Pharmacological studies]. Jpn J Antibiot. 1973 Apr;26(2):130-5. Japanese. PMID: 4147390. 16: Hazato H, Yammamoto T, Tadokoro I, Kawamura A, Suzuki K. [Josamycin propionate 6. Chronic toxicity]. Jpn J Antibiot. 1973 Feb;26(1):1-16. Japanese. PMID: 4541636.