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CAS No 23155-02-4 , [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid

  • Name: [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
  • Synonyms: Fosfonomycin; Fosfomicina; Fosfomycin sodium; Phosphonomycin; Veramina;phosphomycin; Fosfomycine;[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid; Fosfocina;
  • CAS Registry Number:
  • Melting Point: 94 ºC
  • Flash Point: 161.03°C
  • Boiling Point: 342.651°C at 760 mmHg
  • Density: 1.561g/cm3
  • Refractive index: 1.486
  • Safety Statements: Moderately toxic by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of POx.
  • Flash Point: 161.03°C
  • EINECS: 245-463-1
  • Molecular Weight: 138.059042
  • InchiKey: YMDXZJFXQJVXBF-STHAYSLISA-N
  • InChI: InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
  • Molecular Formula: C3H7O4P
  • Molecular Structure:CAS No:23155-02-4 [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid

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23155-02-4 Phosphonicacid, P-[(2R,3S)-3-methyl-2-oxiranyl]-

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23155-02-4 FOSFORMYCIN

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23155-02-4 Phosphonicacid, P-[(2R,3S)-3-methyl-2-oxiranyl]-

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23155-02-4 Fosfomycin

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23155-02-4 Phosphonicacid, P-[(2R,3S)-3-methyl-2-oxiranyl]-

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References of [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Title: Fosfomycin
CAS Registry Number: 23155-02-4
CAS Name: (2R-cis)-(3-Methyloxiranyl)phosphonic acid
Synonyms: (-)-(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)
Synonyms: 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).