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MedKoo Cat#: 318486 | Name: Phenylbutazone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phenylbutazone is a compound of research interest as an anti-inflammatory and anti-proliferative agent. Phenylbutazone acts as a potentent anti-inflammatory agent and mediates prostaglandin synthesis. It also is useful in rheumatoid arthritis and Reiter's syndrome (investigational indication). Phenylbutazone may be of interest regarding research into anti-proliferative effects as well. Phenylbutazone is an inhibitor of Cox (cyclooxygenase) that is also a substrate for peroxidation by Cox.

Chemical Structure

Phenylbutazone
Phenylbutazone
CAS#50-33-9 (free form)

Theoretical Analysis

MedKoo Cat#: 318486

Name: Phenylbutazone

CAS#: 50-33-9 (free form)

Chemical Formula: C19H20N2O2

Exact Mass: 308.1525

Molecular Weight: 308.38

Elemental Analysis: C, 74.00; H, 6.54; N, 9.08; O, 10.38

Price and Availability

Size Price Availability Quantity
25g USD 350.00 2 weeks
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Related CAS #
70145-60-7 (calcium) 129-18-0 (sodium) 50-33-9 (free form)
Synonym
Phenylbutazone; Fenilbutazona; Diphenylbutazone; Butapyrazole; Phenylbutazonum; Butadione; Butapirazol; Butapyrazole; Butazolidin; Diphenylbutazone; Fenilbutazon; Phenylbutazone;
IUPAC/Chemical Name
4-butyl-1,2-diphenylpyrazolidine-3,5-dione
InChi Key
VYMDGNCVAMGZFE-UHFFFAOYSA-N
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
SMILES Code
CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenylbutazone is an efficient reducing cofactor for the peroxidase activity of prostaglandin H synthase (PHS).
In vitro activity:
In the caspase model, 10xIC80t-TUCB significantly decreased whereas 10xIC80 phenylbutazone significantly enhanced apoptosis. Apoptosis enhancement by phenylbutazone was significantly attenuated by concurrent 10xIC80t-TUCB. The remaining treatments and concentrations had no effect on apoptosis development. In the ER stress model, IC50 and IC80 phenylbutazone and firocoxib significantly enhanced apoptosis, which was fully prevented by concurrent 10xIC80t-TUCB. Reference: Res Vet Sci. 2022 Oct;147:44-49. https://pubmed.ncbi.nlm.nih.gov/35447388/
In vivo activity:
This study found that a nonsteroidal anti-inflammatory drug (NSAID), phenylbutazone (PBZ), upregulated the expression of MBNL1 in C2C12 myoblasts as well as in the HSA(LR) mouse model for DM1. In the DM1 mice model, PBZ ameliorated aberrant splicing of Clcn1, Nfix, and Rpn2. PBZ increased expression of skeletal muscle chloride channel, decreased abnormal central nuclei of muscle fibers, and improved wheel-running activity in HSA(LR) mice. Reference: Sci Rep. 2016 Apr 29;6:25317. https://pubmed.ncbi.nlm.nih.gov/27126921/
Solvent mg/mL mM comments
Solubility
DMF 25.0 81.07
DMSO 62.3 202.13
Ethanol 56.0 181.59
PBS (pH 7.2) 0.5 1.62
Water 0.8 2.71
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 308.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Walters B, Trumble TN, Wendt-Hornickle E, Kennedy M, Guedes A. Effects of cyclooxygenase and soluble epoxide hydrolase inhibitors on apoptosis of cultured primary equine chondrocytes. Res Vet Sci. 2022 Oct;147:44-49. doi: 10.1016/j.rvsc.2022.04.002. Epub 2022 Apr 12. PMID: 35447388. 2. Cho JY. Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses. Arch Pharm Res. 2007 Jan;30(1):64-74. doi: 10.1007/BF02977780. PMID: 17328244. 3. Chen G, Masuda A, Konishi H, Ohkawara B, Ito M, Kinoshita M, Kiyama H, Matsuura T, Ohno K. Phenylbutazone induces expression of MBNL1 and suppresses formation of MBNL1-CUG RNA foci in a mouse model of myotonic dystrophy. Sci Rep. 2016 Apr 29;6:25317. doi: 10.1038/srep25317. PMID: 27126921; PMCID: PMC4850456.
In vitro protocol:
1. Walters B, Trumble TN, Wendt-Hornickle E, Kennedy M, Guedes A. Effects of cyclooxygenase and soluble epoxide hydrolase inhibitors on apoptosis of cultured primary equine chondrocytes. Res Vet Sci. 2022 Oct;147:44-49. doi: 10.1016/j.rvsc.2022.04.002. Epub 2022 Apr 12. PMID: 35447388. 2. Cho JY. Immunomodulatory effect of nonsteroidal anti-inflammatory drugs (NSAIDs) at the clinically available doses. Arch Pharm Res. 2007 Jan;30(1):64-74. doi: 10.1007/BF02977780. PMID: 17328244.
In vivo protocol:
1. Chen G, Masuda A, Konishi H, Ohkawara B, Ito M, Kinoshita M, Kiyama H, Matsuura T, Ohno K. Phenylbutazone induces expression of MBNL1 and suppresses formation of MBNL1-CUG RNA foci in a mouse model of myotonic dystrophy. Sci Rep. 2016 Apr 29;6:25317. doi: 10.1038/srep25317. PMID: 27126921; PMCID: PMC4850456.
1: Knych HK, Stanley SD, Seminoff KN, McKemie DS, Kass PH. Pharmacokinetics of methocarbamol and phenylbutazone in exercised Thoroughbred horses. J Vet Pharmacol Ther. 2016 Feb 29. doi: 10.1111/jvp.12298. [Epub ahead of print] PubMed PMID: 26924025. 2: Zhou J, Li X, Zhu X, Sun J, Qiu Q, Huang W, Qian H. Phenylbutazone, a new long-acting agent that can improve the peptide pharmacokinetic based on serum albumin as a drug carrier. Chem Biol Drug Des. 2016 Jan 25. doi: 10.1111/cbdd.12726. [Epub ahead of print] PubMed PMID: 26808199. 3: Lima AG, Costa LC, Alvarenga MA, Martins CB. Does Clinical Treatment with Phenylbutazone and Meloxicam in the Pre-ovulatory Period Influence the Ovulation Rate in Mares? Reprod Domest Anim. 2015 Oct;50(5):771-5. doi: 10.1111/rda.12586. Epub 2015 Aug 17. PubMed PMID: 26280558. 4: Aljuhani N, Whittal RM, Khan SR, Siraki AG. Phenylbutazone Oxidation via Cu,Zn-SOD Peroxidase Activity: An EPR Study. Chem Res Toxicol. 2015 Jul 20;28(7):1476-83. doi: 10.1021/acs.chemrestox.5b00152. Epub 2015 Jul 2. PubMed PMID: 26090772. 5: Martínez Aranzales JR, Cândido de Andrade BS, Silveira Alves GE. Orally administered phenylbutazone causes oxidative stress in the equine gastric mucosa. J Vet Pharmacol Ther. 2015 Jun;38(3):257-64. doi: 10.1111/jvp.12168. Epub 2014 Oct 7. PubMed PMID: 25287371. 6: Conde Ruiz C, Cruz Benedetti IC, Guillebert I, Portier KG. Effect of Pre- and Postoperative Phenylbutazone and Morphine Administration on the Breathing Response to Skin Incision, Recovery Quality, Behavior, and Cardiorespiratory Variables in Horses Undergoing Fetlock Arthroscopy: A Pilot Study. Front Vet Sci. 2015 Nov 23;2:58. doi: 10.3389/fvets.2015.00058. eCollection 2015. PubMed PMID: 26664985; PubMed Central PMCID: PMC4672197. 7: Fourie T, Cromarty D, Duncan N, Wolter K, Naidoo V. The Safety and Pharmacokinetics of Carprofen, Flunixin and Phenylbutazone in the Cape Vulture (Gyps coprotheres) following Oral Exposure. PLoS One. 2015 Oct 29;10(10):e0141419. doi: 10.1371/journal.pone.0141419. eCollection 2015. PubMed PMID: 26512724; PubMed Central PMCID: PMC4626400. 8: Fodey TL, Smyth WG, Barnes P, Traynor IM, Kennedy DG, Crooks SR. Investigation into sources of contamination of cattle with phenylbutazone. Vet Rec. 2015 Jan 17;176(3):74. doi: 10.1136/vr.102839. Epub 2014 Nov 5. PubMed PMID: 25376503. 9: Maciążek-Jurczyk M. Phenylbutazone and ketoprofen binding to serum albumin. Fluorescence study. Pharmacol Rep. 2014 Oct;66(5):727-31. doi: 10.1016/j.pharep.2014.03.005. Epub 2014 Apr 3. PubMed PMID: 25149974. 10: Kivett L, Taintor J, Wright J. Evaluation of the safety of a combination of oral administration of phenylbutazone and firocoxib in horses. J Vet Pharmacol Ther. 2014 Aug;37(4):413-6. doi: 10.1111/jvp.12097. Epub 2013 Dec 20. PubMed PMID: 24354928. 11: Raidal SL, Hughes KJ, Charman AL, Nielsen SG, Phillips JK, Noble GK. Effects of meloxicam and phenylbutazone on renal responses to furosemide, dobutamine, and exercise in horses. Am J Vet Res. 2014 Jul;75(7):668-79. doi: 10.2460/ajvr.75.7.668. PubMed PMID: 24959734. 12: de Grauw JC, van Loon JP, van de Lest CH, Brunott A, van Weeren PR. In vivo effects of phenylbutazone on inflammation and cartilage-derived biomarkers in equine joints with acute synovitis. Vet J. 2014 Jul;201(1):51-6. doi: 10.1016/j.tvjl.2014.03.030. Epub 2014 Apr 1. PubMed PMID: 24888681. 13: Combes RD. Is phenylbutazone a genotoxic carcinogen? A weight-of-evidence assessment. Altern Lab Anim. 2013 Jul;41(3):235-48. Review. PubMed PMID: 23971704. 14: Lees P, Toutain PL. Pharmacokinetics, pharmacodynamics, metabolism, toxicology and residues of phenylbutazone in humans and horses. Vet J. 2013 Jun;196(3):294-303. doi: 10.1016/j.tvjl.2013.04.019. Epub 2013 May 27. Review. PubMed PMID: 23721873. 15: Higgins A. Shutting the stable door after the horse (on phenylbutazone) has bolted. Vet J. 2013 Jun;196(3):273-4. doi: 10.1016/j.tvjl.2013.05.001. Epub 2013 May 23. PubMed PMID: 23707576. 16: Kong CY, Watanabe K, Funazukuri T. Diffusion coefficients of phenylbutazone in supercritical CO2 and in ethanol. J Chromatogr A. 2013 Mar 1;1279:92-7. doi: 10.1016/j.chroma.2013.01.019. Epub 2013 Jan 10. PubMed PMID: 23369749. 17: EC seeks advice on risks from phenylbutazone in horsemeat. Vet Rec. 2013 Mar 23;172(12):306. doi: 10.1136/vr.f1852. PubMed PMID: 23525812. 18: D'Arcy-Moskwa E, Noble GK, Weston LA, Boston R, Raidal SL. Effects of meloxicam and phenylbutazone on equine gastric mucosal permeability. J Vet Intern Med. 2012 Nov-Dec;26(6):1494-9. doi: 10.1111/j.1939-1676.2012.01004.x. Epub 2012 Oct 20. PubMed PMID: 23083114. 19: Henneke D, King S, Day WE, Evans P. Food and Chemical Toxicology, 2010, Association of phenylbutazone usage in horses bought for slaughter: a public health risk. Food Chem Toxicol. 2012 Mar;50(3-4):603; author reply 455-6. doi: 10.1016/j.fct.2012.01.010. Epub 2012 Jan 12. PubMed PMID: 22245664. 20: Soma LR, Uboh CE, Maylin GM. The use of phenylbutazone in the horse. J Vet Pharmacol Ther. 2012 Feb;35(1):1-12. doi: 10.1111/j.1365-2885.2011.01299.x. Epub 2011 Jun 14. Review. PubMed PMID: 21668837.