4254. Fosfomycin

Nomenclature

CAS number: 23155-02-4
(2R-cis)-(3-Methyloxiranyl)phosphonic acid; ()-(1R,2S)-(1,2-epoxypropyl)phosphonic acid; fosfonomycin; phosphonomycin; MK-955.
C3H7O4P; mol wt 138.06.
C 26.10%, H 5.11%, O 46.35%, P 22.44%.

Description and references

Antibiotic produced by Streptomyces strains: D. Hendlin et al., Science 166, 122 (1969); B. G. Christensen et al., ibid. 123; also produced by Pseudomonas syringae: J. Shogi et al., J. Antibiot. 39, 1011 (1986). Isoln: D. Hendlin et al., BE 718507; eidem, US 3914231 (1969, 1975 both to Merck & Co.). Synthesis and resolution: B. G. Christensen et al., BE 723072; BE 723073 (both 1969 to Merck & Co.). Alternate synthesis: Girotra, Wendler, Tetrahedron Lett. 1969, 4647; Glamkowski et al., J. Org. Chem. 35, 3510 (1970). Series of articles on characterization, activity and clinical testing: Antimicrob. Agents Chemother. 1969, 284-351; H. B. Woodruff et al., Chemotherapy 23, Suppl. 1, 1-22 (1977). Mechanism of action: Kahan et al., Ann. N.Y. Acad. Sci. 235, 354 (1974). Pharmacokinetics in humans: M. Goto et al., Antimicrob. Agents Chemother. 20, 393 (1981). Pharmacology of cofosfolactamines, fixed dose combinations of fosfomycin with β-lactam antibiotics: P. Periti, Drugs Exp. Clin. Res. 6, 305 (1980); and clinical trial: T. Barreca et al., ibid. 10, 55 (1984). Electrophoretic determn in biological fluids: D. Levêque et al., J. Chromatogr. B 655, 320 (1994). Clinical trial in cystic fibrosis: A. Mirakhur et al., J. Cyst. Fibros. 2, 19 (2003).

Chemical structure

Properties

Crystals, mp ≈94°. Soluble in water.

Derivative

Benzylammonium salt.
C10H16NO4P; mol wt 245.21.
C 48.98%, H 6.58%, N 5.71%, O 26.10%, P 12.63%.

Properties

mp 170-174°. [α]405 9.1° (c = 5).

Derivative

Calcium salt monohydrate.

Nomenclature

CAS number: 26016-98-8 (anhydrous)
Afos (Salus); Biocin (Ibirn); Biofos (Leben's); Endociclina (Del Saz & Filippini); Faremicin (Lafare); Fonofos (Pulitzer); Fosfobiotic (Bergamon); Fosfocin (Crinos); Fosfocina (C.E.P.A.); Fosfogram (Firma); Fosforal (Fournier); Fosfotricina (Italfarmaco); Fosmicin (Meiji); Foximin (Caber); Francital (Francia); Gram-Micina (Lagap); Ipamicina (IPA); Lancetina (Farma Uno); Lofoxin (Locatelli); Neofocin (Medici); Palmofen (Zambon); Priomicina (San Carlo); Selemicina (Italchemi); Ultramicina (Lisapharma); Valemicina (Farmochim. Ital.).
C3H5CaO4P.H2O; mol wt 194.14.
C 18.56%, H 3.63%, Ca 20.64%, O 41.21%, P 15.95%.

Derivative

Tromethamine.

Nomenclature

CAS number: 78964-85-9
(2R-cis)-(3-Methyloxiranyl)-phosphonic acid compd with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1); fosfomycin trometamol; Monuril (Zambon); Monurol (Zambon).
C7H18NO7P; mol wt 259.19.
C 32.44%, H 7.00%, N 5.40%, O 43.21%, P 11.95%.

Description and references

Clinical trial in urinary tract infection: G. Bonfiglio et al., Chemotherapy (Basel) 51, 162 (2005).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics)