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CAS 55224-05-0

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Erythromycin, cyclic 11,12-carbonate

Description:
Erythromycin, cyclic 11,12-carbonate, is a macrolide antibiotic derived from the bacterium Saccharopolyspora erythraea. It exhibits a broad spectrum of antibacterial activity, primarily targeting Gram-positive bacteria and some Gram-negative organisms. The cyclic carbonate structure enhances its stability and bioavailability, making it effective in treating various bacterial infections, particularly respiratory tract infections, skin infections, and certain sexually transmitted diseases. Erythromycin functions by inhibiting bacterial protein synthesis through binding to the 50S ribosomal subunit, thereby preventing the growth and reproduction of bacteria. This compound is often used as an alternative for patients allergic to penicillin. In terms of physical properties, erythromycin is typically a white to off-white crystalline powder, soluble in water and organic solvents. Its pharmacokinetics involve oral absorption, with metabolism primarily occurring in the liver, and it is excreted mainly through bile. While generally well-tolerated, erythromycin can cause gastrointestinal side effects and may interact with various medications due to its effects on liver enzymes.
Formula:C38H65NO14
InChI:InChI=1S/C38H65NO14/c1-14-25-38(10)32(52-35(44)53-38)20(4)27(40)18(2)16-36(8,45)31(51-34-28(41)24(39(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-37(9,46-13)30(42)23(7)48-26/h18-26,28-32,34,41-42,45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30+,31-,32-,34+,36-,37-,38-/m1/s1
InChI key:InChIKey=NKLGIWNNVDPGCA-ZDYKNUMJSA-N
SMILES:C[C@@]12[C@](OC(=O)O1)([C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]3[C@H](O)[C@@H](N(C)C)C[C@@H](C)O3)[C@@H](C)[C@H](O[C@H]4C[C@](OC)(C)[C@@H](O)[C@H](C)O4)[C@@H](C)C(=O)O[C@@H]2CC)[H]
Synonyms:
  • (1R,2R,5R,6S,7S,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-hydroxy-6-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-1,5,7,9,11,13-hexamethyl-3,15,17-trioxabicyclo[12.3.0]heptadecane-4,12,16-trione
  • (3aR,4R,7R,8S,9S,11R,13R,15R,15aR)-10-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-ethyl-11-hydroxy-8-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3a,7,9,11,13,15-hexamethyloctahydro-4H-[1,3]dioxolo[4,5-c]oxacyclotetradecine-2,6,14(3aH,7H)-trione (non-preferred name)
  • 4H-1,3-Dioxolo[4,5-c]oxacyclotetradecin, erythromycin deriv.
  • Erythromycin A 11,12-carbonate
  • Erythromycin A cyclic 11,12-carbonate
  • Erythromycin cyclic carbonate
  • Erythromycin, cyclic 11,12-carbonate
  • Davercin
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Purity (%)
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