63585-09-1

Basic information

• Product Name: Foscarnet sodium
• Synonyms: Foscarnet sodium Trisodium phosphonoformate;a29622;dihydroxyphosphinecarboxylicacidoxidetrisodiumsalt;phosphinecarboxylicacid,dihydroxy-,oxide,trisodiumsalt;phosphonoformic acid trisodium salt;SODIUM FOSCARNET;trisodium carboxyphosphate;trisodium phosphonoformate
• CAS NO: 63585-09-1
• Molecular Formula: CO₅P*3Na
• Molecular Weight: 191.95
• EINECS: 1312995-182-4
• Product Categories: Miscellaneous Natural Products;API;Foscarnet;Antiviral;Aliphatics;Phosphorylating and Phosphitylating Agents
• Mol File: 63585-09-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: >250°
• Boiling Point: 490.7 °C at 760 mmHg
• Flash Point: 250.6 °C
• Appearance: /
• Vapor Pressure: 5.7E-11mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: Foscarnet sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Foscarnet sodium(63585-09-1)
• EPA Substance Registry System: Foscarnet sodium(63585-09-1)

Safety Data

• Hazardous Substances Data: 63585-09-1(Hazardous Substances Data)

Usage

Description

Foscarnet sodium, also known as phosphonoformic acid trisodium salt, is an antiviral medication used to treat various viral infections, particularly in immunocompromised patients. It is a pyrophosphate analog that inhibits the replication of herpesviruses (CMV, HSV, and VSV) and retroviruses (HIV) by targeting the viral DNA polymerase and reverse transcriptase. Foscarnet sodium does not require bioactivation by viral or cellular enzymes, making it effective against resistant viral strains.

Uses

Used in Antiviral Treatment:
Foscarnet sodium is used as an antiviral agent for the treatment of cytomegalovirus retinitis (CMV retinitis), an inflammation of the retina that can lead to blindness, particularly in immunocompromised patients such as those with AIDS. It is also used as an alternative to ganciclovir for patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to hematological toxicity.
Used in the Treatment of Acyclovir-Resistant HSV Infections:
Foscarnet sodium is the only antiviral approved by the FDA for the treatment of acyclovir-resistant herpes simplex virus (HSV) infections, a growing problem in the AIDS population. It is administered intravenously, reducing the healing time, pain, and viral shedding in patients suspected of having acyclovir-resistant herpes simplex infection.
Used in the Treatment of Retinitis Caused by CMV in AIDS Patients:
Foscarnet sodium is a second-line drug for the treatment of retinitis caused by CMV in patients with AIDS. It helps in managing the condition and reducing the risk of blindness.
Side Effects and Precautions:
Foscarnet sodium therapy is associated with side effects such as azotemia secondary to nephrotoxicity, hyperphosphatemia, hypocalcemia, anemia, nausea, vomiting, and genital ulceration. Patients may eventually develop resistant strains. Metabolic abnormalities, including increases or decreases in blood calcium levels, are common, and nephrotoxicity is a significant concern. Electrolyte imbalances, such as hypocalcemia, hypomagnesemia, hypokalemia, and hypophosphatemia, as well as hyperphosphatemia, are observed in patients treated with foscarnet sodium. Side effects like paresthesias, tetani, seizures, and cardiac arrhythmias may also result.
Brand Name:
Foscarnet sodium is marketed under the brand name Foscavir by AstraZeneca.

Originator

Astra (Sweden)

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

Metabolism

There is no metabolic conversion of foscarnet and it is eliminated by the kidneys as unchanged drug mainly through glomerular filtration, with some active tubular secretion.

InChI:InChI=1/CH3O5P.3Na/c2-1(3)7(4,5)6;;;/h(H,2,3)(H2,4,5,6);;;/q;3*+1/p-3

Upstream product

• 72304-84-8 Ethyl, p-methoxyphenyl phenoxycarbonylphosphonate 
• 119099-01-3 4-Ethyl-4-methyl-3-oxo-1-aminohexan-1,1-diphosphonsaeure 
• 112191-62-5 1-amino-4,4-dimethyl-3-oxo-heptane-1,1-diphosphonic acid 
• 91076-68-5 mono-trimethylsilylphosphite 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 1795-31-9 tris(trimethylsilyl) phosphite 
• 1127-41-9 (α-hydroxybenzyl)phosphonic acid 
• 72304-97-3 Sodium 5-indanyl methoxycarbonylphosphonate 

Relevant articles and documents

Acyloxymethyl and 4-acyloxybenzyl diester prodrugs of phosphonoformate

Sodium pivaloyloxymethyl (pivaloyloxymethoxycarbonyl)phosphonate 4, sodium 4-acyloxybenzyl phenoxycarbonylphosphonates 14a-c and sodium 4-acyloxybenzyl benzyloxycarbonylphosphonates 15a,b have been prepared as bioreversible prodrugs of the antiviral phosphonoformate 1. Their hydrolyses, in vivo systemic bioavailability and antiviral activity are reported. Of the compounds evaluated 4 was the best prodrug.

Synthesis, Properties and Structure of New 1,1-Diphosphonic Acids

The synthesis of 3-tert-alkyl-3-oxo-1-aminopropane-1,1-diphosphonic acids and of 3-tert-alkyl-3-oxo-prop-1-ene-1,1-diphosphonic acids as two new groups of metal complexing agents and their chemical properties are described.Evidence is given for their suggested structures.In addition, the first known example of a diphosphonic acid with a cyano group attached to the geminal carbon atom was prepared from 3-oxo-1-aminoalkane-1,1-diphosphonic acids and 3-tert-alkyl-3-oxo-1-hydroxypropane-1,1-diphosphonic acids from 3-oxo-1-aminopropane-1,1-diphosphonic acids. - Keywords: 3-tert-Alkyl-3-oxo-1-aminopropane-1,1-diphosphonic Acids, 3-tert-Alkyl-3-oxo-1-hydroxypropane-1,1-diphosphonic Acids, 3-tert-Alkyl-3-oxo-prop-1-ene-1,1-diphosphonic Acids, Diphosphonocyanohydrin, Preparation

Synthesis of esters of phosphonoformic acid and their antiherpes activity

Aliphatic and aromatic mono-, di-, and triesters of phosphonoformic (foscarnet) were synthesized. The triesters were prepared by the Michaelis-Arbuzov reaction and were hydrolyzed to di- and monoesters. The compounds were tested for antiviral activity on isolated herpes simplex virus type 1 (HSV-1) DNA polymerase, in a HSV-1 plaque reduction assay, and on a cutaneous HSV-1 infection in guinea pigs. None of the esters inhibited the activity of isolated HSV-1 polymerases. Monoesters with a free carboxylic group and diesters with an aromatic carboxylic ester function were active against the cutaneous herpesa infection. Mono- and diesters with an aromatic phosphonic ester group also showed activity in the plaque-reduction assay. However, mono- and diesters with aliphatic carboxylic ester groups were inactive in all test systems. The results show that all three acidic groups of phosphonoformic acid must be free in order to get antiviral activity at the enzyme level. However, certain esters of this acid may be biotransformed to the acid itself to give antiherpes activity.