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CAS 83905-01-5

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Azithromycin

Description:
Azithromycin is a macrolide antibiotic characterized by its broad-spectrum activity against various bacterial infections. It is derived from erythromycin and is known for its unique structure, which includes a large lactone ring and several sugar moieties. Azithromycin is typically administered orally and is notable for its extended half-life, allowing for once-daily dosing and shorter treatment courses compared to other antibiotics. It works by inhibiting bacterial protein synthesis through binding to the 50S ribosomal subunit, effectively preventing the growth of bacteria. Azithromycin is effective against a range of pathogens, including those responsible for respiratory infections, skin infections, and sexually transmitted diseases. It is generally well-tolerated, with common side effects including gastrointestinal disturbances. Additionally, it has anti-inflammatory properties, which can be beneficial in treating certain conditions beyond bacterial infections. Its pharmacokinetics, including good tissue penetration and accumulation in cells, contribute to its efficacy in treating infections. Azithromycin is also included in treatment regimens for certain atypical infections and is often used in combination therapies.
Formula:C38H72N2O12
InChI:InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChI key:InChIKey=MQTOSJVFKKJCRP-BICOPXKESA-N
SMILES:O([C@@H]1[C@@H](C)[C@H](O[C@H]2C[C@](OC)(C)[C@@H](O)[C@H](C)O2)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@]1(C)O)[C@H]3[C@H](O)[C@@H](N(C)C)C[C@@H](C)O3
Synonyms:
  • (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-<smallcap>D</span>-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one
  • (2R,3S,4R,5S,6R,8R,11S,12R,13R,14S)-5-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-6,12,13-trihydroxy-3-[(2S,4R,5S,6R)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-2,4,6,8,10,11,13-heptamethyl-15-oxa-10-azacyclopentadecan-1-one
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-<smallcap>D</span>-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-<smallcap>D</span>-xylo-hexopyranosyl]oxy]-, [2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*)]-
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-
  • 1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, [2R-(2R*,3S*,4R*,5R*,8R*,10R*,11R*,12S*,13S*,14R*)]-
  • 1-Oxa-6-azacyclopentadecan-15-one,13-((2,6-dideoxy-3-C-methyl-1-3-O-methyl-alpha-L-ribo-hexopyranosyl)-oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)
  • 11-(4-Dimethylamino-3-Hydroxy-6-Methyl-Oxan-2-Yl)Oxy-2-Ethyl-3,4,10-Tr
  • 9-Deoxo-9-methyl-9a-aza-9-homoerythromycin A
  • 9-Deoxo-9a-methyl-9a-aza-9a-homoetrythromycin A
  • See more synonyms
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