FOSCARNET TRISODIUM SALT
Foscarnet
CAS: 63585-09-1
Molecular Formula: CNa3O5P
FOSCARNET TRISODIUM SALT - Names and Identifiers
| Name | Foscarnet |
| Synonyms | a29622 Foscavir Foscarnet Foscarnet sodium FOSCARNET SODIUM Foscarnet sodium Sodiumphosphonatoformate FOSCARNET TRISODIUM SALT Trisodium phosphonoformate Trisodium carboxyphosphate trisodium phosphonato carbonate Phosphonoformic acid, trisodium salt trisodium dioxidophosphanecarboxylate oxide trisodium dioxidophosphinecarboxylate oxide Foscarnet sodium Trisodium phosphonoformate Phosphinecarboxylic acid, dihydroxy-, oxide, trisodium salt |
| CAS | 63585-09-1 |
| EINECS | 695-653-7 |
| 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 |
FOSCARNET TRISODIUM SALT - Physico-chemical Properties
| Molecular Formula | CNa3O5P |
| Molar Mass | 191.95 |
| Melting Point | >250° |
| Boling Point | 490.7°C at 760 mmHg |
| Flash Point | 250.6°C |
| Vapor Presure | 5.7E-11mmHg at 25°C |
| Storage Condition | Inert atmosphere,Room Temperature |
| Physical and Chemical Properties | Hexahydrate: crystalline, melting point> 250 °c. |
| Use | Used as an antiviral drug |
| In vitro study | Foscarnet Sodium is able to penetrate into cells and inhibit viral replication by inhibiting viral DNA synthesis. Foscarnet Sodium (300 μm) acted on H9 cells infected with HTLV-Ⅲ and inhibited more than 95% of HTLV-Ⅲ reverse transcriptase activity. Foscarnet Sodium has low cytotoxicity and inhibits cell proliferation at high concentrations. 0.5-1 mM Foscarnet Sodium inhibited DNA synthesis and/or cell proliferation by 50% when incubated with HeLa cells or primary human lung fibroblasts for 24-48 H. Foscarnet Sodium can bind to the heparin binding domain of FGF2 and inhibit the cell proliferation induced by fgf2. Foscarnet Sodium (25 μm) treatment of HUVEC cells for 48 hours reduced fgf2-induced cell proliferation by 20%. Treatment of CAL-62 cells with Foscarnet Sodium (0.5-1 mM) for 24 h CAL-62 cells, a human thyroid undifferentiated cancer cell line expressing FGF2, reduced cell proliferation by nearly 80%. |
| In vivo study | Foscarnet Sodium is effective in treating animals infected with viral diseases such as skin infections, herpetic keratitis, genital infections, or systemic and intracerebral infections. For example, starting 48 hours after virus inoculation, 30 μl of Foscarnet Sodium (100 mM) was locally dripped for 4 days. After inoculation with HSV-1 strain C42, the cumulative score was reduced by more than 70%. Foscarnet Sodium (20 mg/kg) administered as an aerosol to mice infected with murine cytomegalovirus (CMV) caused a 60% decrease in lung titers. |
FOSCARNET TRISODIUM SALT - Risk and Safety
| Toxicity | LD50 i.p. in mice: 2000-4000 mmol/kg (Eriksson) |
FOSCARNET TRISODIUM SALT - Nature
Open Data Verified Data
The content of cos PNa3 shall not be less than 98 based on the dry product. 5% and not more than 101.0%; PH value should be 9.0~11.0(2.O% aqueous solution); Containing heavy metals shall not be greater than 0.002%; Phosphate content shall not be greater than 0.45%; Phosphite content shall not be greater than 0. 38%; The content of esters shall not be more than 0.5%; The content of triethyl phosphonate shall not be more than 0.1%; The loss on drying shall not be less than 35.0% and shall not be more than 37.0%.
Last Update：2024-01-02 23:10:35
FOSCARNET TRISODIUM SALT - Preparation Method
Open Data Verified Data
The reaction of phosphorus trichloride and ethanol gave triethyl phosphite. Triethyl phosphite is reacted with ethyl chloroformate to obtain triethyl phosphonate. Triethyl phosphonate was dissolved in an aqueous solution of sodium hydroxide, refluxed, cooled and filtered to obtain the hexahydrate of sodium phosphonate. Alternatively, the finely divided sodium cyanide is placed in carbon tetrachloride, diethyl phosphite is added dropwise, the reaction is completed, filtered, concentrated, and distilled under reduced pressure to obtain dihexyl cyanophosphate. This was refluxed with sodium hydroxide, filtered, and recrystallized from water to give foscarnet sodium hexahydrate.
Last Update：2022-01-01 09:08:16
FOSCARNET TRISODIUM SALT - Use
Open Data Verified Data
The German Astra company developed, launched in Virus, a broad-spectrum anti-Virus drug that inhibits the replication of herpes Virus by inhibiting DNA polymerase. Compared with other antiviral drugs, no side effects such as bone marrow cumulative toxicity. For cytomegalovirus retinitis. It is also used in the treatment of osteoporosis.
Last Update：2022-01-01 09:08:16
FOSCARNET TRISODIUM SALT - Safety
Open Data Verified Data
mice were intraperitoneally injected with LD50:2000-4000umol/kg.
Last Update：2022-01-01 09:08:16
FOSCARNET TRISODIUM SALT - Reference Information
| biological activity | Foscarnet Sodium (phoshonoformate) inhibits Virus of RNA polymerase, reverse transcriptase, DNA polymerase by non-competitive inhibition of dNTPs. |
| Target | Value |
| Use | The pyrophosphate analog inhibits the replication of herpes Virus by inhibiting Virus DNA polymerase. Compared with other antiviral drugs, no side effects such as bone marrow cumulative toxicity. For cytomegalovirus retinitis. It is also used in the treatment of osteoporosis. use as antiviral agent |
| production method | Method 1: In the absence of an organic base, phosphorus trichloride and ethanol form diethyl phosphite; triethyl phosphite is obtained in the presence of an organic base. After the reaction of triethyl phosphite and ethyl chloroformate at 160 ° C., a fraction of 148-150 ° C./2.40KPA was collected to obtain triethyl phosphonate in a yield of 71%. Diethyl phosphite in anhydrous diethyl ether, in the presence of sodium metal, and ethyl chloroformate at room temperature, also can get triethyl phosphonate, yield 80%. 21 parts of triethyl phosphonate were dissolved in 60 parts of water containing 24 parts of 50% sodium hydroxide and refluxed for 2H. Cool overnight and filter to give 4.7 parts of the hexahydrate of sodium foscarnet, melting point> 250 °c. Method 2: Freshly ground sodium cyanide was placed in carbon tetrachloride, and equimolar diethyl phosphite was added dropwise at about 10 °c, followed by reaction at 35 °c for 3 hours. Diethyl cyanophosphate was obtained by filtration, concentration and distillation under reduced pressure, yield 72%, boiling point 88-91 ℃/1.46kPa. This was refluxed with 40% sodium hydroxide for 2H, filtered, and recrystallized from water to give foscarnet sodium hexahydrate in 52% yield with a melting point> 250 °c. |
Last Update：2024-04-10 22:29:15
