Fosfomycin

Title: Fosfomycin
CAS Registry Number: 23155-02-4
CAS Name: (2R-cis)-(3-Methyloxiranyl)phosphonic acid
Additional Names: (-)-(1R,2S)-(1,2-epoxypropyl)phosphonic acid; fosfonomycin; phosphonomycin
Manufacturers' Codes: MK-955
Molecular Formula: C3H7O4P
Molecular Weight: 138.06
Percent Composition: C 26.10%, H 5.11%, O 46.35%, P 22.44%
Literature 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 b-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. Fibr. 2, 19 (2003).
Properties: Crystals, mp ~94°. Soluble in water.
Melting point: mp ~94°
Derivative Type: Benzylammonium salt
Molecular Formula: C10H16NO4P
Molecular Weight: 245.21
Percent Composition: C 48.98%, H 6.58%, N 5.71%, O 26.10%, P 12.63%
Properties: mp 170-174°. [a]405 -9.1° (c = 5).
Melting point: mp 170-174°
Optical Rotation: [a]405 -9.1° (c = 5)
Derivative Type: Calcium salt monohydrate
CAS Registry Number: 26016-98-8 (anhydrous)
Trademarks: 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.)
Molecular Formula: C3H5CaO4P.H2O
Molecular Weight: 194.14
Percent Composition: C 18.56%, H 3.63%, Ca 20.64%, O 41.21%, P 15.95%
Derivative Type: Tromethamine
CAS Registry Number: 78964-85-9
CAS Name: (2R-cis)-(3-Methyloxiranyl)-phosphonic acid compd with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)
Additional Names: fosfomycin trometamol
Trademarks: Monuril (Zambon); Monurol (Zambon)
Molecular Formula: C7H18NO7P
Molecular Weight: 259.19
Percent Composition: C 32.44%, H 7.00%, N 5.40%, O 43.21%, P 11.95%
Literature References: Clinical trial in urinary tract infection: G. Bonfiglio et al., Chemotherapy (Basel) 51, 162 (2005).
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics).
Fosfosal Fosinopril Fosmidomycin Fosphenytoin Fospirate

Fosfomycin
FosfomycinImage.svg
Systematic (IUPAC) name
[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Clinical data
Trade names Monurol
AHFS/Drugs.com monograph
MedlinePlus a697008
Pregnancy cat. B (US)
Legal status -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 30–37% (oral, fosfomycin tromethamine); varies with food intake
Protein binding Nil
Metabolism Nil
Half-life 5.7 hours (mean)
Excretion Renal and fecal, unchanged
Identifiers
CAS number 23155-02-4 YesY 78964-85-9
ATC code J01XX01
PubChem CID 446987
DrugBank DB00828
ChemSpider 394204 YesY
UNII 2N81MY12TE YesY
KEGG D04253 YesY
ChEBI CHEBI:28915 YesY
ChEMBL CHEMBL1757 YesY
Chemical data
Formula C3H7O4P 
Mol. mass 138.059 g/mol
 YesY (what is this?)  (verify)

Fosfomycin (also known as phosphomycin, phosphonomycin and the trade name Monurol) is a broad-spectrum antibiotic[1] produced by certain Streptomyces species. It can now be made by chemical synthesis.