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CAS 110205-60-2

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8,9-Didehydro-N-demethyl-N-ethylerythromycin A 6,9-hemiketal

Description:
8,9-Didehydro-N-demethyl-N-ethylerythromycin A 6,9-hemiketal is a semi-synthetic derivative of erythromycin, which is a macrolide antibiotic. This compound is characterized by its unique structural modifications that enhance its pharmacological properties. The presence of the 8,9-didehydro configuration contributes to its increased stability and potency against certain bacterial strains. The N-demethyl and N-ethyl substitutions are significant as they influence the compound's solubility and bioavailability. The 6,9-hemiketal formation is crucial for its mechanism of action, allowing it to effectively inhibit bacterial protein synthesis by binding to the 50S ribosomal subunit. This compound exhibits a broad spectrum of antibacterial activity, particularly against Gram-positive bacteria and some Gram-negative organisms. Its pharmacokinetic profile, including absorption, distribution, metabolism, and excretion, is also influenced by these structural features, making it a valuable option in clinical settings for treating various infections. As with other macrolides, it may also exhibit side effects and interactions with other medications, necessitating careful consideration in therapeutic use.
Formula:C38H67NO12
InChI:InChI=1/C38H67NO12/c1-14-26-38(11,44)31(41)21(5)29-19(3)17-37(10,51-29)33(50-35-28(40)25(39(12)15-2)16-20(4)46-35)22(6)30(23(7)34(43)48-26)49-27-18-36(9,45-13)32(42)24(8)47-27/h20-28,30-33,35,40-42,44H,14-18H2,1-13H3/t20-,21-,22+,23-,24+,25+,26-,27+,28-,30-,31-,32+,33+,35+,36-,37+,38-/m1/s1
Synonyms:
  • 8,9-Didehydro-N-demethyl-9-deoxo-6-deoxy-6,9-epoxy-N-ethylerythromycin
  • EM-523
  • (2S,3R,4S,5R,8R,9R,10S,11S,12S)-5-ethyl-11-({(2S,3R,4S,6R)-4-[ethyl(methyl)amino]-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl}oxy)-3,4-dihydroxy-9-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-2,4,8,10,12,14-hexamethyl-6,15-dioxabicyclo[10.2.1]pentadec-1(14)-en-7-one (non-preferred name)
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