| Identification | Back Directory | [Name]
JOSAMYCIN | [CAS]
16846-24-5 | [Synonyms]
C12662
EN 141
Jomybel
Josacine
Josamina
Iosalide
YL-704A3
Vilprafen
Wilprafen
JOSAMYCIN
lucamycin
turimycina5
kitasamycina3
LEUCOMYCIN A3
Josamycin CRS
Pre-validation
Josamycin Standard
antibioticyl-704a3
Josamycin solution
Leucomycin A3 (8CI)
JOSAMYCIN USP/EP/BP
Leucomycin A3 (>90%)
JOSAMYCIN(16846-24-5)
Sparsentan Impurity 65
Josamycin Solution, 100ppm
Josamycin for peak identification
Josamycin solution solution,1000ppm
3-acetate4(supb)-(3-methylbutanoate)
Josamycin for peak identification CRS
LEUCOMYCIN V,3-ACETA 4β-(3-METHYL BUTANOATE)
3-Acetate 4B-(3-Methylbutanoate)leucoMycin V
LEUCOMYCIN V,3-AC-ETA 4B-(3-METHYLBUTANOATE)
LeucoMycin V, 3-acetate4B-(3-Methylbutanoate)
Leucomycin V 3-acetate 4''-(3-methylbutanoate)
LEUCOMYCIN V,3-ACETA 4BETA-(3-METHYL BUTANOATE)
leucomycinv,3-acetate4(supb)-(3-methylbutanoate)
Leucomycin V, 3-acetate 4B-(3-methylbutanoate) (9CI)
(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
(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) | [EINECS(EC#)]
240-871-6 | [Molecular Formula]
C42H69NO15 | [MDL Number]
MFCD00211043 | [MOL File]
16846-24-5.mol | [Molecular Weight]
827.99 |
| Chemical Properties | Back Directory | [Appearance]
White or slightly yellowish powder, slightly hygroscopic. | [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. ]
2-8°C
| [solubility ]
Soluble in ethanol | [form ]
powder | [pka]
7.1 (40% aq methanol) | [color ]
white to slightly yellow | [Merck ]
13,5286 | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Chemical Properties]
White or slightly yellowish powder, slightly hygroscopic. | [Uses]
A 16-membered ring macrolide antibiotic with antimicrobial activity against a wide range of pathogens. Particularly used in the treatment of Mycoplasma infection. | [Definition]
ChEBI: A macrolide antibiotic produced by certain strains of Streptomyces narbonensis var. josamyceticus. | [Originator]
Josalid,Biochemie | [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. |
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