4251. Foscarnet Sodium

Nomenclature

CAS number: 63585-09-1
1,1-Dihydroxyphosphinecarboxylic acid 1-oxide sodium salt (1:3); dihydroxyphosphinecarboxylic acid oxide trisodium salt; trisodium phosphonoformate; trisodium carboxyphosphate; A-29622.
CNa3O5P; mol wt 191.95.
C 6.26%, Na 35.93%, O 41.68%, P 16.14%.

Description and references

Pyrophosphate analog; inhibits viral DNA polymerase and reverse transcriptase. Prepn: P. Nylén, Ber. 57B, 1023 (1924). Crystal structure: R. R. Naqvi et al., J. Chem. Soc. A 1971, 2751; S. C. Abrahams, Acta Crystallogr. B28, 2886 (1972). Activity against herpes simplex virus: E. Helgstrand et al., Science 201, 819 (1978). Effect on HIV-1 reverse transcriptase: P. S. Sarin et al., Biochem. Pharmacol. 34, 4075 (1985). HPLC determn in plasma: B. B. Ba et al., J. Chromatogr. B 724, 127 (1999); in pharmaceutical formulations: J. Garcia et al., Biomed. Chromatogr. 20, 1024 (2006). Series of articles on pharmacology and clinical experience in cytomegalovirus retinitis: Am. J. Med. 92, Suppl. 1, S1-S35 (1992). Clinical trial in multi-drug resistant HIV infection: A. Canestri et al., Antivir. Ther. 11, 561 (2006).

Chemical structure

Derivative

Hexahydrate.

Nomenclature

CAS number: 34156-56-4
Foscavir (AstraZeneca).
CNa3O5P.6H2O; mol wt 300.04.
C 4.00%, Na 22.99%, O 58.66%, P 10.32%, H 4.03%.

Properties

White or almost white, crystalline powder. mp >250°. Sol in water. Practically insol in ethanol.

Therapeutic Category

Antiviral.

Keywords

Antiviral; Reverse Transcriptase Inhibitor