Phosphonoformic acid trisodium salt hexahydrate CAS 34156-56-4

Introduction：Basic information about Phosphonoformic acid trisodium salt hexahydrate CAS 34156-56-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Phosphonoformic acid trisodium salt hexahydrate Basic information

• Product Name: Phosphonoformic acid trisodium salt hexahydrate
• Synonyms: Foscarnet, Phosphonoformic acid hexahydrate trisodium salt;Sodium phosphonoformate hexahydrate tribasic;trisodium phosphonatoformate hexahydrate;trisodium phosphonatomethanoate hexahydrate;Foscarnet Sodium (50 mg);1,1-Dihydroxyphosphinecarboxylic Acid 1-Oxide SodiuM Salt Hydrate;A 29622 Hydrate;EHB 776 Hydrate
• CAS: 34156-56-4
• MF: CH6NaO6P
• MW: 168.02
• Product Categories: Phosphonic/Phosphinic Acid Salts;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Organic Building Blocks;Phosphorus Compounds;S;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 34156-56-4.mol

Phosphonoformic acid trisodium salt hexahydrate Chemical Properties

• storage temp.: 2-8°C
• solubility: H₂O: 0.1 g/mL hot, clear, colorless
• form: Solid
• color: White to off-white
• Water Solubility: Soluble in water.
• Major Application: pharmaceutical (small molecule)
• InChI: InChI=1S/CH3O5P.Na.H2O.H/c2-1(3)7(4,5)6;;;/h(H,2,3)(H2,4,5,6);;1H2;
• InChIKey: ILRVASBWNRYBFD-UHFFFAOYSA-K
• SMILES: P(O)(O)(=O)C(=O)O.[NaH].O
• CAS DataBase Reference: 34156-56-4(CAS DataBase Reference)

Safety Information

• Hazard Codes: Xi
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: SY8300000
• HS Code: 29319090
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Muta. 2 STOT RE 2

Phosphonoformic acid trisodium salt hexahydrate Usage And Synthesis

Chemical Properties

Phosphonoformic acid trisodium salt hexahydrate is white or almost white, crystalline powder.

Uses

Foscarnet inhibits viral DNA polymerase and reverse transcriptase. Foscarnet is used as an antiviral.

Uses

Sodium phosphonoformate hexahydrate acts as an antiviral agent and reverse transcriptase inhibitor. It is also used to inhibit viral DNA polymerase. Further, it is used as a type II Pi transporter inhibitor.

Definition

ChEBI: The hexahydrate form of trisodium phosphonoformate. It is used as an antiviral agent in the treatment of cytomegalovirus retinitis (CMV retinitis, an inflamation of the retina that can lead to blindness) and as an alternative to ganciclovir for AIDS patiens who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity.

Acquired resistance

Phosphonoformic acid trisodium salt hexahydrate can be generated in vitro, and CMV strains resistant to both ganciclovir and foscarnet have occasionally been recovered from humans.

Pharmaceutical Applications

Phosphonoformic acid trisodium salt hexahydrate is a synthetic non-nucleoside pyrophosphate analog formulated as the trisodium hexahydrate for intravenous use. The solubility in water at pH 7 is only about 5% (w/w).

Pharmacokinetics

Oral absorption: c. 17%
C_max 60 mg/kg intravenous 8-hourly: 557 μmol/L
Plasma half-life: 3.3–6.8 h
Volume of distribution: 0.52–0.74 L/kg
Plasma protein binding: 14–17%
Absorption and distribution
Oral bioavailability is poor. A wide range of plasma concentrations was noted (75–500 μmol/L) during 3–21 days of continuous intravenous infusion of 0.14–0.19 mg/kg per min. During continuous intravenous therapy the concentrations reached a plateau on day 3. Considerable differences in steady-state plasma concentrations exist between individuals. Drug penetrates the CSF; the mean concentration is about 40–60% of the mean plasma concentration, depending upon dose.
Metabolism and excretion
Elimination appears to be triphasic, with two initially short half-lives of 0.5–1.4 h and 3.3–6.8 h, followed by a long terminal phase of 88 h. About 88% of the cumulative intravenous dose is recovered unchanged in the urine within a week of stopping an infusion, indicating that the drug is not significantly metabolized. Non-renal clearance accounts for 14–18% of total clearance and may relate to uptake into bone. Plasma clearance decreases markedly with decreased renal function and the elimination half-life may be increased by up to 10-fold. Conventional dialysis eliminates about 25% of a dose while high-flux dialysis can remove nearly 60%.

Clinical Use

Treatment of CMV retinitis in patients for whom ganciclovir iscontraindicated, inappropriate or ineffective
It is also potentially of value in the treatment of aciclovir-resistantHSV infection.

Side effects

Treatment is more frequently limited by toxicity than with ganciclovir.Renal toxicity is most common. A two- to three-foldincrease in serum creatinine levels occurs in 20–60% (mean45%) of patients given 130–230 mg/kg per day as a continuousintravenous infusion. Renal impairment usually developswithin the first few weeks of treatment and is generally reversiblewithin several weeks of discontinuing therapy. Foscarnetchelates metal ions, and serum electrolyte abnormalities –predominantly hypocalcemia, hypomagnesemia, hypokalemiaand hypophosphatemia – occur in about 30, 15, 16 and 8%of patients, respectively. Convulsions occur in 10–15%. Otherside effects include anemia (25–50%), penile or vulval ulceration(3–9%), nausea and vomiting (20–30%), local irritationand thrombophlebitis at the infusion site, abdominal pain andoccasional pancreatitis, headache (c. 25%), dizziness, involuntarymuscle contractions, tremor, hypoesthesia, ataxia, neuropathy,anxiety, nervousness, depression and confusion, andskin rash. Nephrogenic diabetes insipidus has been reported.
Foscarnet is contraindicated in pregnancy. Topical applicationdoes not result in dermal toxicity similar to that producedby phosphonacetic acid.

Phosphonoformic acid trisodium salt hexahydrate Preparation Products And Raw materials

• Preparation Products: Foscarnet sodium