Sodium phosphonoformate

To the resultant triethyl phosphonoformate (105 g, 0.5 mol) was added sodium hydroxide solution (250 ml, 10 M) over a period of 15 min at ambient temperature. The solution became hot, and ethanol by-product boiled off from the reaction mixture. Upon cooling, a precipitate formed, which was recrystallized from water to give colorless crystals of the pure trisodium phosphonoformate hexahydrate (27.5 g, 19%), which exhibited IR and NMR spectra and x-ray crystal analysis in accord with the proposed structure. 

R. P. Iyer, J. H. Boal, L. R. Phillips, D. R. Thakker, W. Egan, Synthesis, Hydrolytic Behavior, and Anti-HIV Activity of Selected Acyloxyalkyl Esters of Trisodium Phosphonoformate (Foscarnet Sodium) , J. Pharm. Sci. 1994, 83, 1269- 1273. 

Common Name Foscarnet sodium Foscarnetum natricum Trisodium phosphonoformate... 

The wet substance is recrystallized in 570 ml of water by heating to 423 g (4.77 mol) of sodium hydroxide liquid cone, is added to 400 ml of water. The solution is heated to about 50°C and 167 g (0.795 mol) of triethyl phosphonoformate is added at this temperature. The reaction mixture is then heated to about 90°C and ethanol formed is distilled off. After about 1 hour at 90-95°C the reaction mixture is cooled to about 20°C and the product is filtered off. The yield of trisodium phosphonoformate hexahydrate wet is 248... 

Iyer, R.P., Phillips, L.R., Biddle, J.A., Thakker, D.R., Egan, W., Aoki, S., and Mitsuya, H., Synthesis of acyloxyalkyl acylphosphonates as potential prodrugs of the antiviral, trisodium phosphonoformate (foscarnet sodium). Tetrahedron Lett., 30, 7141, 1989. 

These two compounds may possess some clinical advantage over ara-A due to their low systemic toxicity. The antiviral effects of phosphonoformic acid (PFA, foscarnet sodium), which is presently in Phase III clinical trials in Europe, 3 have been discussed in a recent review.91 The synthesis and structural requirements for antiherpes activity of a series of PFA esters have also been reported.92... 

Foscamet (phosphonoformic acid, 4,22) is an anti-viral which acts by binding to the pyrophosphate-combining site of DNA polymerase, but only on the virus-specified enzyme. It is usually applied topically to the lesions of herpes (Larsson and Oberg, 1981). Sodium phosphonoacetate acts similarly (Overby, Duff and Mao, 1977). 

TEPA. See Tetraethylenepentamine TEPA. See Triethyl phosphonoacetate TEPF. See Triethyl phosphonoformate Tephaprint RV. See Sodium polyacrylate Tephasoft CT-W. See Silicone TEP-HP. See Triethyl phosphite TEPP. See Tetraethyl pyrophosphate Tequat BC. See Cetrimonium chloride Tequat PAN. See Lauralkonium chloride Terathane 650r, Terathane 1000] Terathane ... 

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