| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Prostaglandin H synthase (PHS) / Cyclooxygenase (COX). Phenylbutazone is an efficient reducing cofactor for the peroxidase activity of prostaglandin H synthase (PHS). It also acts as a nonsteroidal anti-inflammatory agent (NSAID) by inhibiting cyclooxygenase (COX) enzymes, with an IC50 of approximately 100 uM for the peroxidase activity in the presence of hydrogen peroxide. It also inhibits prostaglandin I synthase with an IC50 of ~25 uM.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
In vitro, Phenylbutazone(diphenyl-d10) is used primarily as an internal standard for the quantitation of its parent compound. Its non-labeled parent, phenylbutazone, is an efficient reducing cofactor for the peroxidase activity of prostaglandin H synthase (PHS). It also inhibits prostaglandin I synthase (PGI synthase) with an IC50 of ~25 uM. Phenylbutazone induces muscle blind-like protein 1 (MBNL1) expression. |
| ln Vivo |
No detailed in vivo studies are reported for the labeled form. The non-deuterated phenylbutazone is an NSAID used historically for its anti-inflammatory, analgesic, and antipyretic effects. It is used in veterinary medicine for the treatment of musculoskeletal disorders, particularly in horses. It reduces inflammation and pain by inhibiting COX enzymes and blocking prostaglandin synthesis.
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| Enzyme Assay |
A COX inhibition assay is performed using purified ovine COX-1 and COX-2 enzymes. The enzymes are pre-incubated with serially diluted phenylbutazone (0.1-1000 uM) for 10 minutes in the presence or absence of hydrogen peroxide (which supports the peroxidase reaction). Arachidonic acid (100 uM) is added, and the reaction proceeds for 2 minutes. The reaction is stopped, and PGE2 is measured by ELISA. The IC50 for the peroxidase activity of PHS is calculated (~100 uM in the presence of hydrogen peroxide). PGI synthase inhibition is assessed using purified enzyme.
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| Cell Assay |
For in vitro cellular assays, immortalized human hepatocyte cell lines (e.g., HepG2) are treated with phenylbutazone (0.1-1000 uM) for 24-72 hours to assess hepatotoxicity and MBNL1 expression. Cell viability is measured by MTT or CellTiter-Glo assay. MBNL1 mRNA and protein levels are quantified by qRT-PCR and Western blot. LDH release is measured as a marker of cytotoxicity. For internal standard use, phenylbutazone(diphenyl-d10) is added to samples (e.g., plasma, urine, liver homogenates) before LC-MS/MS analysis.
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| Animal Protocol |
No in vivo animal studies are performed for the labeled form alone. For pharmacokinetic studies, animals (e.g., rats or dogs) are administered phenylbutazone orally (10-100 mg/kg) or intravenously. Blood and tissue samples are collected at multiple time points. Phenylbutazone(diphenyl-d10) is added to each sample as an internal standard before LC-MS/MS analysis to quantify phenylbutazone and its metabolites (e.g., oxyphenbutazone). Pharmacokinetic parameters (Cmax, Tmax, half-life, AUC) are calculated.
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| ADME/Pharmacokinetics |
Phenylbutazone(diphenyl-d10) has a molecular weight of 318.44 g/mol and a formula of C19H10D10N2O2. It is the deuterated analog of phenylbutazone. The non-deuterated phenylbutazone is orally bioavailable, highly plasma protein-bound (>99%), and has a long half-life (50-100 hours in humans, 3-6 hours in rodents). It is metabolized by CYP enzymes to oxyphenbutazone (active metabolite) and conjugates, excreted in urine and bile.
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| Toxicity/Toxicokinetics |
Phenylbutazone is a known hepatotoxin and can cause bone marrow suppression (agranulocytosis, aplastic anemia) in humans. It has been withdrawn from human use in many countries due to these severe toxicities. The compound can also cause gastrointestinal ulceration, fluid retention, and renal impairment. Phenylbutazone(diphenyl-d10) should be handled as a potential carcinogen and hepatotoxin. Due to its toxicity, it is no longer used as a human therapeutic but remains in veterinary medicine.
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| References |
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| Additional Infomation |
Phenylbutazone(diphenyl-d10) is a research-grade stable isotope-labeled compound not approved for clinical use in humans. It is intended for use as an internal standard in LC-MS/MS quantification of phenylbutazone and its metabolites in biological matrices for drug metabolism, pharmacokinetic, and forensic toxicology studies. Phenylbutazone is a prototypical NSAID used primarily in veterinary medicine. This product is for laboratory research only.
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| Molecular Formula |
C19H20N2O2
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|---|---|
| Molecular Weight |
308.374304771423
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| Exact Mass |
318.215
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| CAS # |
1219794-69-0
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| Related CAS # |
Phenylbutazone;50-33-9
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| PubChem CID |
154735120
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| Appearance |
White to off-white solid powder
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| LogP |
3.2
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
23
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| Complexity |
389
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C(C(N(C2C=CC=CC=2)N1C1C=CC=CC=1)=O)CCCC
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| InChi Key |
VYMDGNCVAMGZFE-MIPJZDBJSA-N
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| InChi Code |
InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3/i4D,5D,6D,7D,8D,9D,10D,11D,12D,13D
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| Chemical Name |
4-butyl-1,2-bis(2,3,4,5,6-pentadeuteriophenyl)pyrazolidine-3,5-dione
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 3.2429 mL | 16.2143 mL | 32.4286 mL | |
| 5 mM | 0.6486 mL | 3.2429 mL | 6.4857 mL | |
| 10 mM | 0.3243 mL | 1.6214 mL | 3.2429 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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