Basic information
- CAS
63585-09-1- Standard SMILES
O=C([O-])P(=O)([O-])[O-].[Na+].[Na+].[Na+]- InChIKey
DFHAXXVZCFXGOQ-UHFFFAOYSA-K- Molecular formula
- CNa3O5P
- Average molar mass
- 191.95 g/mol
- Monoisotopic mass
- 191.91764294
Overview
Trisodium phosphonoformate is the trisodium salt of phosphonoformic acid. 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 patients who require concurrent antiretroviral therapy but are unable to tolerate ganciclovir due to haematological toxicity. It has a role as an antiviral drug. It is an organic sodium salt and a one-carbon compound. It contains a phosphonatoformate.
Names & identifiers
- Preferred name
- Foscarnet Sodium
- IUPAC
- trisodium;phosphonatoformate
- English name
- Foscarnet sodium
- Molecular formula
- CNa3O5P
- Molecular weight
- 191.95
Names & synonyms
FOSCARNET SODIUM63585-09-1FoscavirFoscarnet sodicoEHB 776Phosphonoformic acid, trisodium saltPhosphinecarboxylic acid, dihydroxy-, oxide, trisodium saltEHB-776Foscarnet sodium anhydrousfoscarnet de sodio8C5OQ81LWTA-29622
Show more names
FOSCARNETTriaptena29622Foscanet sodiumfoscarnet sodimSODIUM FOSCARNETPhenytion SodiumFOSCARNET SODIUM USP
NSC-313410NSC-758148CHEBI:141644NSC313410RefChem:55233Phosphonoformate Trisodium964YS0OOG1Foscarnet Sodium Hexahydrate
Database identifiers
- CAS
63585-09-1- PubChem CID
- 44561
- DTXSID
DTXSID6023078- ChEMBL
CHEMBL754- ChEBI
CHEBI:141644- UNII
- 8C5OQ81LWT
Properties
Computed structural properties
- Topological polar surface area
- 103 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 103
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 250 ° · >250°
- storage temp.
- Inert atmosphere,Room Temperature
- form
- Solid
- color
- White to off-white
- Water Solubility
- 24.9 mg/mL · ≥ 24.9mg/mL in water
- InChI
- InChI=1S/CH3O5P.3Na/c2-1(3)7(4,5)6;;;/h(H,2,3)(H2,4,5,6);;;/q;3*+1/p-3
- InChIKey
- DFHAXXVZCFXGOQ-UHFFFAOYSA-K
- SMILES
- [Na+].[Na+].[Na+].C(P([O-])([O-])=O)([O-])=O
- CAS DataBase Reference
- 63585 · 63585-09-1(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- foscarnet sodium; Foscavir
- FDA UNII
- 8 C5OQ81LWT · 8C5OQ81LWT
- ATC code
- 5 AD01 · J05AD01
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
P203, P260, P280, P318, P319, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 9 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesMuta. 2 (100%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Foscarnet sodium
Ambiguous-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- Toxicity
- LD50 i.p. in mice: 2000-4000 mmol/kg (Eriksson)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H319
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
FOSCARNET SODIUM
DNA Polymerase Inhibitors [MoA]; Pyrophosphate Analog DNA Polymerase Inhibitor [EPC]; Chelating Activity [MoA]; Pyrophosphate Analog [EXT]
MeSH Pharmacological Classification
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >100
Applications
DescriptionFoscamet 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.
UsesInhibits 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.
Related reactions
0 records
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Compound notes
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