Printed from: The Merck Index. [online] Fourteenth Edition, Whitehouse Station, NJ: Merck & Co., Inc.

10555. Fidaxomicin
Nomenclature
CAS number: 873857-62-6 (3E,5E,8S,9E,11S,12R,13E,15E,18S)-3-[[[6-Deoxy-4-O-(3,5-dichloro-2-ethyl-4,6-dihydroxybenzoyl)-2O-methyl--D-mannopyranosyl]oxy]methyl]-12-[[6-deoxy-5-C-methyl-4-O-(2-methyl-1-oxopropyl)-D-lyxo-hexopyranosyl]oxy]-11-ethyl-8-hydroxy-18-[(1R)-1-hydroxyethyl]-9,13,15trimethyloxacyclooctadeca-3,5,9,13,15-pentaen-2-one; lipiarmycin A3; tiacumicin B; clostomicin B1; OPT-80; PAR-101. C52H74Cl2O18; mol wt 1058.04. C 59.03%, H 7.05%, Cl 6.70%, O 27.22%.

Description and references

Macrolide antibiotic with activity against Clostridium difficile; inhibits bacterial RNA polymerase. Major component of the antibiotic complex originally isolated as lipiarmycin from a strain of Actinoplanes deccanensis. Isoln of complex: C. Coronelli et al., DE 2455230; eidem, US 3978211 (1975, 1976 both to Lepetit). Mechanism of action: M. Talpaert et al., Biochem. Biophys. Res. Commun. 63, 328 (1975) DOI PubMed. Isoln of lipiarmycins A3 and A4 and elucidation of structure: A. Arnone et al., J. Chem. Soc. Perkin Trans. 1 1987, 1353 DOI. Isoln as tiacumicin B from Dactylosporangium aurantiacum subsp. hamdenensis: R. J. Theriault et al., J. Antibiot. 40, 567 (1987) PubMed; J. E. Hochlowski et al., ibid., 575 PubMed. Prepn of crystalline polymorphs: Y.-H. Chiu et al., US 7378508 (2008 to Optimer). Antibacterial spectrum vs anaerobes: K. L. Credito, P. C. Appelbaum, Antimicrob. Agents Chemother. 48, 4430 (2004) DOI PubMed. Clinical pharmacokinetics: Y. K. Shue et al., ibid. 52, 1391 (2008) DOI PubMed. Clinical evaluation in C. difficile infection: T. Louie et al., ibid. 53, 223 (2009) DOI PubMed. Review of development and clinical experience: K. M. Sullivan, L. M. Spooner, Ann. Pharmacother. 44, 352-359 (2010) DOI PubMed; M. Miller, Expert Opin. Pharmacother. 11, 1569-1578 (2010) DOI PubMed.

Properties
White crystals from ethyl acetate + hexane, mp 161-165 (Arnone). Also reported as white needles from isopropanol, mp 166-169 (Chiu). []D -6.9 ( c = 2.0 in methanol). Sol in methanol, isopropanol, acetonitrile, ethyl acetate. Practically insol in water. 09/12/2011 07:25 p.m.

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Therapeutic Category
Antibacterial. Keywords Antibacterial (Antibiotics); Macrolides

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09/12/2011 07:25 p.m.