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Josamycin

Product Name
Josamycin
CAS No.
16846-24-5
Chemical Name
Josamycin
Synonyms
C12662;EN 141;Jomybel;YL-704A3;Iosalide;Josacine;Josamina;Wilprafen;Vilprafen;JOSAMYCIN
CBNumber
CB5444692
Molecular Formula
C42H69NO15
Formula Weight
827.99
MOL File
16846-24-5.mol
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Josamycin Property

Melting point:
131.5℃
alpha 
D25 -70° (c = 1 in ethanol)
Boiling point:
763.27°C (rough estimate)
Density 
1.1547 (rough estimate)
refractive index 
1.6220 (estimate)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Soluble in ethanol
form 
powder
pka
7.1 (40% aq methanol)
color 
white to slightly yellow
Merck 
13,5286
Stability:
Hygroscopic
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Safety

WGK Germany 
2
RTECS 
OH4725810
F 
10
Toxicity
LD50 oral in rat: > 7gm/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0000041
Product name
Josamycin
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0000041
Price
$220
Updated
2024/03/01
Sigma-Aldrich
Product number
59983
Product name
Josamycin
Purity
≥98.0% (UV)
Packaging
50mg
Price
$65.8
Updated
2024/03/01
Alfa Aesar
Product number
J62245
Product name
Josamycin, 98+%
Packaging
50mg
Price
$93.65
Updated
2024/03/01
Cayman Chemical
Product number
29606
Product name
Josamycin
Packaging
50mg
Price
$53
Updated
2024/03/01
Cayman Chemical
Product number
29606
Product name
Josamycin
Packaging
100mg
Price
$93
Updated
2024/03/01
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Josamycin Chemical Properties,Usage,Production

Chemical Properties

Josamycin is a macrolide substance having antibacterial activity produced by the growth of Streptomyces narboensis var. josamyceticus.
Josamycin appears as white to yellowish white powder, slightly hygroscopic. Josamycin is very soluble in methanol or in ethanol, and very slightly soluble in water.

Originator

Josalid,Biochemie

Uses

Josamycin, is used as a macrolide antibiotic effective against a variety of pathogens.

Uses

As a 16-membered ring macrolide antibiotic with antimicrobial activity against a wide range of pathogens. Josamycin can be particularly used in the treatment of Mycoplasma infection.
Josamycin is used to study the modification of phagocytosis and cytokine production by macrolide antibiotics, immunomodulatory effects, the suppression of matrix metalloproteinase production as well as study bacteria protein synthesis at the level of the the 23S rRNA, 50S ribosomal subunit.

Definition

ChEBI: A macrolide antibiotic produced by certain strains of Streptomyces narbonensis var. josamyceticus.

Manufacturing Process

100 ml of a culture medium consisting of water containing 1.5% soybean meal, 1% starch, 1% glucose, 0.3% sodium chloride, 0.1% dipotassium hydrogen phosphate, and 0.05% magnesium sulfate was placed in a 500 ml flask and sterilized for 20 min at 120°C. After cooling, the culture medium was inoculated with strain A 205-P2 Streptomyces narbonensis var. josatny ceticus, and the strain was subjected to shaking culture at 27°-29°C and at 130 strokes per min and 8 cm amplitude. After 3 days of culture, the culture fluids in such 100 flasks were combined together and filtered to give 8700 ml of culture filtrate. The pH of the filtrate was 6.4 and showed an inhibition zone of 25 mm. to Bacillus subtilis (PCI 219 strain). The filtrate was extracted with 8700 ml of ethyl acetate. The extract (7300 ml) thus obtained was concentrated to 730 ml under vacuum at temperatures lower than 50°C, 360 ml of water added, and then concentrated hydrochloric acid added to ad just the pH to 2.0, whereby josamycin was transferred to the aqueous layer. After adjusting the pH of the aqueous layer to 7.5 by the addition of 0.1 N sodium hydroxide, josamycin was extracted with 180 ml of ethyl acetate.
Josamycin was then transferred to 90 ml of an aqueous solution at pH 2.0 and extracted again with 45 ml of ethyl acetate as above process. Ethyl acetate solution thus obtained was evaporated under reduced pressure to give a solidified product, which was dissolved in 5 ml of benzene to remove impurities and the product, solidified from the benzene solution by evaporating under reduced pressure, was dissolved in a small amount of ethyl acetate and subjected to an alumina chromatography. That is, Brockman alumina (Merck) was treated with hydrochloric acid, sufficiently rinsed with water, and activated by heating for 5 h at 150°C.
50.0 g of thus treated alumina was filled in a glass tube of 1.6 cm in diameter by using ethyl acetate. The above prepared ethyl acetate solution was added to the alumina column and the product was eluted with 200 ml of ethyl acetate. The eluate thus obtained was concentrated under reduced pressure and the solid product thus obtained was dissolved in 5 ml of benzene and 50 ml of n-hexane added to give 0.18 g of amorphous josamycin having a purity of above 90%.

Therapeutic Function

Antibiotic

Pharmaceutical Applications

A naturally occurring antibiotic produced by Streptomyces narbonensis var. josamyceticus and belonging to the leucomycin group of macrolides. It is formulated for oral administration.
Many Gram-positive and Gram-negative anaerobes are susceptible, including Peptostreptococcus spp., Propionibacterium spp., Eubacterium spp. and Bacteroides spp.
After a single 1 g oral dose, a peak serum concentration of 2.74 mg/L was achieved 0.75 h after dosing. The AUC was 4.2 mg.h/L, and the apparent elimination half-life 1.5 h. Several inactive metabolites could be detected. It penetrates into saliva, tears and sweat, and achieves high levels in bile and lungs. It is mostly metabolized and excreted in the bile in an inactive form. Less than 20% of the dose appears in the urine, producing levels of around 50 mg/L.
The drug is generally well tolerated, producing only mild gastrointestinal disturbance. Its uses are similar to those of erythromycin. It is of limited availability.

Biological Activity

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.

Josamycin Preparation Products And Raw materials

Raw materials

Preparation Products

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Josamycin Suppliers

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View Lastest Price from Josamycin manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Josamycin 16846-24-5
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-28
Hebei Yanxi Chemical Co., Ltd.
Product
Josamycin 16846-24-5
Price
US $20.00-2.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-09-15
airuikechemical co., ltd.
Product
josamycin 16846-24-5
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.99%
Supply Ability
20 tons
Release date
2024-04-10

16846-24-5, JosamycinRelated Search:

DL-CARNITINE Josamycin 2',9-dipropionate,Josamycin 9,2'-dipropionate,Josamycin dipropionate JOSAMYCIN EPY(CRM STANDARD) JOSAMYCIN PROPIONATE EPY(CRM STANDARD) JOSAMYCIN MM(CRM STANDARD) JOSAMYCIN PROPIONATE Deisovaleryl josamycin E,E-8,10-DODECADIEN-1-YL ACETATE 4-(Dimethylamino)tetrahydro-2H-pyran 2-Ethylhexyloxypropylamine Josamycin methyl 3-(acetoxy)octanoate 8,10-DODECADIEN-1-OL ISO-PROPYL-UNDECYLENATE ETHYL 3 ACETOXY HEXANOATE DL-3-ACETOXYBUTYRIC ACID ETHYL ESTER

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  • JOSAMYCIN
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  • (2S,3S,4R,6S)-6-(((2R,3S,4R,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)-5-hydroxy-2-methyltetrahydro-2H-pyran-3-yl)oxy)-4-hydroxy-2,4-
  • [(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-dimethyloxa
  • Pre-validation
  • JOSAMYCIN(16846-24-5)
  • (4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-6-[[3,6-dideoxy-4-O-[2,6-dideoxy-3-C-methyl-4-O-(3-methylbutanoyl)-α-L-ribo-hexopyranosyl]-3-(dimethylamino)-β-D-glucopyranosyl]oxy]-10-hydroxy-5-methoxy-9,16-dimethyl-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-2-one (josamycin)
  • Leucomycin A3 (>90%)
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  • LA14495000ALJosamycin 10μg/mLin Acetonitrile.
  • Josamycin in Acetonitrile
  • Sparsentan Impurity 65
  • 16846-24-5
  • C42H69NO15
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