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CAS 16846-24-5

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Josamycin

Description:
Josamycin is a macrolide antibiotic that is primarily derived from the fermentation of the bacterium Streptomyces narbonensis. It is characterized by its ability to inhibit bacterial protein synthesis by binding to the 50S ribosomal subunit, thereby preventing the growth of susceptible bacteria. Josamycin exhibits a broad spectrum of activity against various Gram-positive bacteria and some Gram-negative organisms, making it effective in treating respiratory tract infections, skin infections, and certain sexually transmitted diseases. The compound is typically administered orally and is known for its favorable pharmacokinetic properties, including good tissue penetration and a relatively long half-life. Josamycin is also notable for its low toxicity profile, which contributes to its therapeutic use. However, like other antibiotics, it can lead to the development of antibiotic resistance if misused. Its chemical structure includes a large lactone ring, which is a common feature of macrolide antibiotics, contributing to its biological activity and stability.
Formula:C42H69NO15
InChI:InChI=1/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
InChI key:InChIKey=XJSFLOJWULLJQS-NGVXBBESSA-N
SMILES:O([C@@H]1[C@@H](OC)[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@@H]1CC=O)[C@H]2[C@H](O)[C@@H](N(C)C)[C@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(CC(C)C)=O)[C@H](C)O3)[C@@H](C)O2
Synonyms:
  • (2S,3R,4R,6S)-6-{[(2R,3S,4R,5R,6S)-6-{[(4R,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-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-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate (non-preferred name)
  • (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)oxacyclohexadeca-11,13-dien-6-yl]oxy}-4-(dimethylamino)-5-hydroxy-2-methyltetrahydro-2H-pyran-3-yl]oxy}-4-hydroxy-2,4-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate (non-preferred name)
  • 6-{[6-{[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-(acetyloxy)-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-dimethyltetrahydro-2H-pyran-3-yl 3-methylbutanoate (non-preferred name)
  • Antibiotic YL 704A3
  • Antibiotic YL 704A<sub>3</sub>
  • En 141
  • Iosalide
  • Jomybel
  • Josacine
  • Josamicina
  • See more synonyms
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Purity (%)
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50
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90
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95
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100
Found 16 products.