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| Targets |
Sparfosic acid targets viral DNA polymerases by mimicking pyrophosphate, a product of DNA polymerization. It binds to the pyrophosphate binding site on the polymerase enzyme, preventing the incorporation of nucleotides into the growing DNA chain. This inhibits viral DNA replication. The compound shows selectivity for viral DNA polymerases over host DNA polymerases, contributing to its antiviral activity.
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| ln Vitro |
In drug-resistant Br1 cells, spadrin (N-(phosphonacetyl)-L-aspartic acid, PALA) induces apoptosis [1]. At 300 µM, spafosic acid causes apoptotic pathways to be activated, which results in cell death, and a gradual buildup of S phase cells [1].
In vitro, sparfosic acid inhibits the replication of herpes simplex virus (HSV) and varicella-zoster virus (VZV) in cell culture. Its activity is assessed by measuring the reduction in viral titers or by using plaque reduction assays. The compound demonstrates dose-dependent inhibition of viral replication. Specific IC50 values for viral inhibition are not detailed in the provided search results. Sparfosic acid also inhibits the activity of purified viral DNA polymerases in cell-free assays. |
| ln Vivo |
Mice with B16 melanoma given 490 mg/kg of spafosic acid intraperitoneally on days 1, 5, and 9 demonstrated higher lifespans—between 77% and 86% longer than controls. Sparfosic acid sensitivity in Lewis lung carcinoma is high. Half of the mice who received treatment for Lewis lung carcinoma on days 1, 5, and 9 following subcutaneous implantation recovered [4].
In vivo, sparfosic acid has been studied for its antiviral efficacy in animal models of HSV infection. The compound's ability to inhibit viral replication and reduce disease severity has been evaluated. However, its clinical development has been limited due to the availability of more effective and better-tolerated antiviral agents such as acyclovir. |
| Enzyme Assay |
The in vitro activity of sparfosic acid is assessed using cell-based antiviral assays. Cells (e.g., Vero cells) are infected with HSV or VZV in the presence of varying concentrations of sparfosic acid. Viral replication is assessed by plaque reduction assay or by measuring viral DNA by qPCR. The IC50 is determined from dose-response curves. For cell-free assays, purified viral DNA polymerase is incubated with a DNA template, nucleotides, and varying concentrations of sparfosic acid, and polymerase activity is measured by incorporation of radiolabeled nucleotides.
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| Cell Assay |
Cell viability assay [1]
Cell Types: Br-1 and L-2 cell lines established by nude mouse transfer injected with the human tumor cell line MDA-MB-435 Tested Concentrations: 300 µM Incubation Duration: 12, 24 and 48 hrs (hours) Experimental Results: Two Cells in the seed cell line are mainly in S phase, but the proportion of S phase cells in L-2 is slightly higher than that in Brl-3prl cells. Western Blot Analysis[1] Cell Types: Br-1 and L-2 Cell lines Tested Concentrations: 300 µM Incubation Duration: 4, 10 and 24 hrs (hours) Experimental Results: There was a moderate difference in the levels of phosphorylated Rb protein in the two cell types. A significant increase in the amount of cyclin A protein was detected in apoptotic L-2 cells, with the highest levels detected 10 hrs (hours) after drug treatment. In contrast, cyclin A levels were not increased in Brl-3prl cells. Cyclin E protein was increased in L-2 cells and Brl-3prl cells compared with respective controls. For cellular assays, Vero cells or other susceptible cell lines are cultured in appropriate media. Cells are infected with virus at a multiplicity of infection (MOI) of 0.01-1 and treated with various concentrations of sparfosic acid (typically 0.1-1000 μM) for 24-72 hours. Viral replication is assessed by plaque assay or by measuring viral DNA by qPCR. Cell viability is assessed using standard assays to ensure that observed effects are not due to cytotoxicity. |
| Animal Protocol |
In vivo, sparfosic acid is typically administered topically or systemically to animal models of HSV infection. In topical models, the compound is applied to infected skin lesions, and lesion severity and viral shedding are assessed. In systemic models, the compound is administered orally or intraperitoneally, and survival or disease severity is assessed. Specific dosing regimens and efficacy outcomes are not detailed in the provided search results.
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| ADME/Pharmacokinetics |
Sparfosic acid has a molecular weight of 140.03 g/mol and a molecular formula of C2H5O5P. It is a small, hydrophilic compound. The compound is soluble in water and should be stored under appropriate conditions to maintain stability. Specific pharmacokinetic parameters such as bioavailability and half-life are not detailed in the provided search results.
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| Toxicity/Toxicokinetics |
Sparfosic acid can cause local irritation when applied topically. Systemic administration may be associated with toxicity, including effects on bone metabolism due to its structural similarity to pyrophosphate. The compound should be used with caution and appropriate safety precautions. Comprehensive toxicological studies are required to establish its full safety profile.
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| References |
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| Additional Infomation |
Sparfolate is a solid. This compound belongs to the N-acyl-α-amino acid class of compounds. These compounds have an acyl group at the terminal nitrogen atom of the α-amino acid. It is known to target the aspartate carbamoyltransferase catalytic chain and CAD proteins. Sparfolate is a stable transition state analog of the aspartate carbamoyltransferase-catalyzed antitumor response. Sparfolate is a stable transition state analog of the activation complex of the aspartate carbamoyltransferase-catalyzed reaction (the first step in the pyrimidine biosynthesis pathway). This drug inhibits de novo pyrimidine synthesis and increases the incorporation of fluorouracil metabolites into RNA.
Sparfosic acid (phosphonoacetic acid) is a research compound that was studied for its antiviral activity against herpes viruses. It was one of the first pyrophosphate analogs developed as antiviral agents. However, its clinical development was limited due to the availability of more effective and better-tolerated antiviral drugs such as acyclovir. Sparfosic acid is not approved for clinical use and is intended for research purposes only. It is available from chemical suppliers for research applications. |
| Molecular Formula |
C6H10NO8P
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| Molecular Weight |
255.11
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| Exact Mass |
255.014
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| CAS # |
51321-79-0
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| Related CAS # |
Sparfosic acid trisodium;70962-66-2
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| PubChem CID |
39981
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| Appearance |
Colorless to light yellow liquid
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| LogP |
-3.1
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
16
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| Complexity |
346
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C(C(C(=O)O)NC(=O)CP(=O)(O)O)C(=O)O
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| InChi Key |
ZZKNRXZVGOYGJT-VKHMYHEASA-N
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| InChi Code |
InChI=1S/C6H10NO8P/c8-4(2-16(13,14)15)7-3(6(11)12)1-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)(H2,13,14,15)/t3-/m0/s1
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| Chemical Name |
(2S)-2-[(2-phosphonoacetyl)amino]butanedioic acid
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| Synonyms |
NSC-224131; Acide sparfosique; Sparfosic Acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~125 mg/mL (~489.97 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9199 mL | 19.5994 mL | 39.1988 mL | |
| 5 mM | 0.7840 mL | 3.9199 mL | 7.8398 mL | |
| 10 mM | 0.3920 mL | 1.9599 mL | 3.9199 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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