Flurithromycin

Last updated
Flurithromycin
Flurithromycin.svg
Clinical data
ATC code
Identifiers
  • (3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6-
    [(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-
    6-methyloxan-2-yl]oxy-14-ethyl-9-fluoro-7,12,
    13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-
    4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,
    11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.126.548 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C37H66FNO13
Molar mass 751.927 g·mol−1
3D model (JSmol)
  • O=C3O[C@H](CC)[C@](O)(C)[C@H](O)[C@H](C(=O)[C@](F)(C)C[C@](O)(C)[C@H](O[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O)[C@H]([C@H](O[C@@H]2O[C@H]([C@H](O)[C@](OC)(C2)C)C)[C@H]3C)C)C
  • InChI=1S/C37H66FNO13/c1-14-24-37(10,46)29(42)21(5)28(41)34(7,38)17-35(8,45)31(52-33-26(40)23(39(11)12)15-18(2)48-33)19(3)27(20(4)32(44)50-24)51-25-16-36(9,47-13)30(43)22(6)49-25/h18-27,29-31,33,40,42-43,45-46H,14-17H2,1-13H3/t18-,19+,20-,21+,22+,23+,24-,25+,26-,27+,29-,30+,31-,33+,34+,35-,36-,37-/m1/s1 Yes check.svgY
  • Key:XOEUHCONYHZURQ-HNUBZJOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Flurithromycin is a second generation macrolide antibiotic. It is a fluorinated derivative of erythromycin A. [1] It is a broad spectrum antibiotic with similar bactericidal action to erythromycin. Unlike erythromycin, flurithromycin is more tolerant of acidic environments, meaning more survives the digestion process, resulting in higher serum levels, and more efficacious elimination of susceptible bacteria, including staphylococcus aureus and streptococcus pyogenes. [2]

References

  1. ↑ Gialdroni Grassi G, Alesina R, Bersani C, Ferrara A, Fietta A, Peona V (June 1986). "In vitro activity of flurithromycin, a novel macrolide antibiotic". Chemioterapia. 5 (3): 177–184. PMID   3487389.
  2. ↑ Kaneko T, Dougherty TJ, Magee TV (January 2007). "7.18 - Macrolide Antibiotics". In Taylor JB, Triggle DJ (eds.). Comprehensive Medicinal Chemistry II. Oxford: Elsevier. pp. 519–566. doi:10.1016/b0-08-045044-x/00219-4. ISBN   978-0-08-045044-5.
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