Flurithromycin

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]

Flurithromycin
Clinical data
ATC code
Identifiers
IUPAC name
  • (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 InfoCard100.126.548
Chemical and physical data
FormulaC37H66FNO13
Molar mass751.927 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 Y
  • Key:XOEUHCONYHZURQ-HNUBZJOYSA-N Y
 NY (what is this?)  (verify)

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: International Journal of the Mediterranean Society of Chemotherapy. 5 (3): 177–84. PMID 3487389.
  2. Kaneko, T.; Dougherty, T. J.; Magee, T. V. (2007-01-01), Taylor, John B.; Triggle, David J. (eds.), "7.18 - Macrolide Antibiotics", Comprehensive Medicinal Chemistry II, Oxford: Elsevier, pp. 519–566, doi:10.1016/b0-08-045044-x/00219-4, ISBN 978-0-08-045044-5, retrieved 2022-08-03


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