Foscarnet sodium

Base Information

• Chemical Name: Foscarnet sodium
• CAS No.: 63585-09-1
• Molecular Formula: CO₅P*3Na
• Molecular Weight: 191.951
• Hs Code.: 2942000000
• Mol file: 63585-09-1.mol

Synonyms:Phosphinecarboxylicacid, dihydroxy-, oxide, trisodium salt (9CI);A 29622;EHB 776;Foscavir;Gefin;Phosphonoformic acid trisodium salt;Triapten;Trisodium phosphonoformate;Foscarnet Sodium;

Chemical Property of Foscarnet sodium

Chemical Property:

• Appearance/Colour: White or almost white crystalline powder
• Vapor Pressure: 5.7E-11mmHg at 25°C
• Melting Point: 62-65°C(lit.)
• Boiling Point: 490.7 °C at 760 mmHg
• Flash Point: 250.6 °C
• PSA: 113.13000
• LogP: -0.61620
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99%min ^*data from raw suppliers

Foscarnet Sodium ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Description: Foscamet sodium is a new, injectable antiviral agent useful in the treatment of severe cytomegalovirus retinitis in immunodepressed patients. Foscarnet sodium acts by inhibiting viral-specific DNA polymerases; its side-effects include decreased hemoglobin levels and acute tubular necrosis.
• Uses: Inhibits viral DNA polymerase and reverse transcriptase. Foscarnet is the only antiviral approved by the FDA for the treatment of acyclovir-resistant HSV infections, a growing problem in the AIDS population. Foscarnet does not require HSV-encoded thymidine kinase. Foscarnet therapy reduces the healing time, pain, and viral shedding. It is administered intravenously, 40 mg/kg every 8 to 12 hours within 7 to 10 days in patients suspected of having acyclovir-resistant herpes simplex infection. Foscarnet is administered for 10 days. Associated side effects include azotemia secondary to nephrotoxicity, hyperphosphatemia, hypocalcemia, anemia, nausea, vomiting, and genital ulceration. Patients may eventually develop resistant strains. Preliminary trials indicate that topical 1%foscarnet cream may have some benefit for the treatment of acyclovir-resistant mucocutaneous HSV infection in patients with AIDS.
• Therapeutic Function: Antiviral
• Clinical Use: Foscarnet sodium was approved by the U.S. FDA for the treatment of CMV retinitis in patients with AIDS. In combination with ganciclovir, the results have been promising, even in progressive disease with ganciclovir-resistant strains. Foscarnet sodium also is effective in the treatment of mucocutaneous diseases caused by acyclovir-resistant strains of HSV and VZV in patients with AIDS. Foscarnet sodium is administered IV at 60 mg/kg three times a day for initial therapy and at 90 to 120 mg/kg daily for maintenance therapy. The plasma-half life is 3 to 6 hours. Foscarnet sodium penetrates into the CSF and the eye. The drug is neurotoxic, and common adverse effects include phlebitis, anemia, nausea, vomiting, and seizures. Foscarnet sodium carries the risk of severe hypocalcemia, especially with concurrent use of IV pentamidine. Foscarnet sodium used with zidovudine (ZDV) has an additive effect against CMV and acts synergistically against HIV.
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: may cause acute renal failure in combination. Pentamidine: increased risk of hypocalcaemia with parenteral pentamidine

Technology Process of Foscarnet sodium

There total 7 articles about Foscarnet sodium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

Ethyl, p-methoxyphenyl phenoxycarbonylphosphonate (72304-84-8) → foscarnet (63585-09-1,66706-14-7,111964-97-7) + p-Methoxyphenyl disodium oxycarbonylphosphonate (74270-25-0)

Guidance literature:

With sodium hydroxide; trimethylsilyl bromide; for 5h;

DOI:10.1021/jm00356a028

Reference yield:

sodium 4-n-butanoyloxybenzyl phenoxycarbonylphosphonate → (4-hydroxyphenyl)methanol (623-05-2) + foscarnet (63585-09-1,66706-14-7,111964-97-7) + disodium phenoxycarbonylphosphonate (74270-30-7)

Guidance literature:

With porcine liver carboxyesterase; at 37 ℃; Product distribution; other triesters and diesters; also in tissue (rat liver and rat intestine) homogenates; var. solvents;

DOI:10.1016/0040-4020(96)00906-4

Reference yield:

4-Ethyl-4-methyl-3-oxo-1-aminohexan-1,1-diphosphonsaeure (119099-01-3) → foscarnet (63585-09-1,66706-14-7,111964-97-7) + (4-Ethyl-4-methyl-3-oxo-1-phosphono-hex-1-enyl)-phosphonic acid

Guidance literature:

With sodium hydroxide; at 120 ℃; for 48h;

upstream raw materials:

Ethyl, p-methoxyphenyl phenoxycarbonylphosphonate

4-Ethyl-4-methyl-3-oxo-1-aminohexan-1,1-diphosphonsaeure

1-amino-4,4-dimethyl-3-oxo-heptane-1,1-diphosphonic acid

mono-trimethylsilylphosphite

Downstream raw materials:

(α-hydroxybenzyl)phosphonic acid

Sodium 5-indanyl methoxycarbonylphosphonate

tris(trimethylsilyl) phosphite

Refernces

• 1、 Balszuweit, A.,Issleib, K.,Moeglein, W.,Stiebitz, B.. "A NEW APPROACH TO P-C BOND FORMATION BY USING TRIMETHYLSILYL PHOSPHITES". . p. 778. Retrieved 2007/10/02.
• 2、 -. "Method for combating virus infection". . . Retrieved 2008/06/13.