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CAS 144604-03-5

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(10E)-10,11-Didehydro-11-deoxy-6-O-methylerythromycin

Description:
(10E)-10,11-Didehydro-11-deoxy-6-O-methylerythromycin 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 didehydro group at the 10 and 11 positions contributes to its increased potency against certain bacterial strains, while the 11-deoxy modification helps in reducing susceptibility to bacterial resistance mechanisms. The 6-O-methyl group further alters its solubility and bioavailability. This compound exhibits antibacterial activity primarily against Gram-positive bacteria and some Gram-negative bacteria, making it useful in treating various infections. Its mechanism of action involves inhibiting bacterial protein synthesis by binding to the 50S ribosomal subunit. Additionally, (10E)-10,11-Didehydro-11-deoxy-6-O-methylerythromycin may have a favorable pharmacokinetic profile, allowing for effective oral administration. However, like other antibiotics, it is essential to use it judiciously to minimize the risk of developing antibiotic resistance.
Formula:C38H67NO12
InChI:InChI=1S/C38H67NO12/c1-15-27-36(8,44)17-20(2)29(40)21(3)18-38(10,46-14)33(51-35-30(41)26(39(11)12)16-22(4)47-35)23(5)31(24(6)34(43)49-27)50-28-19-37(9,45-13)32(42)25(7)48-28/h17,21-28,30-33,35,41-42,44H,15-16,18-19H2,1-14H3/b20-17+/t21-,22-,23+,24-,25+,26+,27-,28+,30-,31+,32+,33-,35+,36+,37-,38-/m1/s1
InChI key:InChIKey=XBRPMQCVVSGOJB-LUHVZOSXSA-N
SMILES:O([C@H]1[C@@](OC)(C)C[C@@H](C)C(=O)\C(\C)=C\[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@](OC)(C)[C@@H](O)[C@H](C)O2)[C@@H]1C)[C@H]3[C@H](O)[C@@H](N(C)C)C[C@@H](C)O3
Synonyms:
  • Erythromycin, 10,11-didehydro-11-deoxy-6-O-methyl-, (10E)-
  • Oxacyclotetradecane, erythromycin deriv.
  • (10E)-10,11-Didehydro-11-deoxy-6-O-methylerythromycin
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