Phenylbutazone

For research use only. Not for therapeutic Use.

  • CAT Number: A000932
  • CAS Number: 50-33-9
  • Molecular Formula: C19H20N2O2
  • Molecular Weight: 308.4
  • Purity: ≥95%
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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.


Catalog Number A000932
CAS Number 50-33-9
Synonyms

50-33-9; Fenilbutazona; Butazolidin; Diphenylbutazone; 4-Butyl-1,2-diphenylpyrazolidine-3,5-dione

Molecular Formula C19H20N2O2
Purity ≥95%
Target COX
Storage -20°C
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
InChIKey VYMDGNCVAMGZFE-UHFFFAOYSA-N
SMILES CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
Reference

1: Singh A, Hakk H, Lupton SJ. Facile synthesis of high specific activity
4-[1-(14) C]butyl-1,2-diphenylpyrazolidine-3,5-dione (phenylbutazone) using
nucleophilic substitution. J Labelled Comp Radiopharm. 2017 Dec 23. doi:
10.1002/jlcr.3597. [Epub ahead of print] PubMed PMID: 29274290.

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2: Pedersen SK, Cribb AE, Read EK, French D, Banse HE. Phenylbutazone induces
equine glandular gastric disease without decreasing prostaglandin E(2)
concentrations. J Vet Pharmacol Ther. 2017 Nov 16. doi: 10.1111/jvp.12464. [Epub
ahead of print] PubMed PMID: 29148168.
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3: UCVM Class of 2016, Banse H, Cribb AE. Comparative efficacy of oral meloxicam
and phenylbutazone in 2 experimental pain models in the horse. Can Vet J. 2017
Feb;58(2):157-167. PubMed PMID: 28216685; PubMed Central PMCID: PMC5234315.
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4: Boison JO, Dowling P, Matus JL, Kinar J, Johnson R. The Analysis of
Phenylbutazone and Its Active Metabolite, Oxyphenbutazone, in Equine Tissues
(Muscle, Kidney, and Liver), Urine, and Serum by LC-MS/MS. J AOAC Int. 2017 Jul
1;100(4):1110-1122. doi: 10.5740/jaoacint.16-0127. Epub 2017 Feb 1. PubMed PMID:
28145218.
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5: Barnes P, Fodey TL, Smyth WG, Crooks SR. Investigation of the role of
environmental contamination in the occurrence of residues of the veterinary drug
phenylbutazone in cattle. Food Addit Contam Part A Chem Anal Control Expo Risk
Assess. 2017 Apr;34(4):520-524. doi: 10.1080/19440049.2016.1271143. Epub 2017 Jan
31. PubMed PMID: 28140763.
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6: Haddad C, Chosidow O, Valeyrie-Allanore L, Ghaleh B, Legrand T, Mockenhaupt M,
Barau C, Khoudour N, Sekula P, Wolkenstein P, Hulin A. Are Idiopathic
Stevens-Johnson Syndrome/Toxic Epidermal Necrolysis Related to Drugs in Food? The
Example of Phenylbutazone. J Invest Dermatol. 2017 May;137(5):1179-1181. doi:
10.1016/j.jid.2016.11.041. Epub 2017 Jan 17. PubMed PMID: 28108296.
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7: Burkett BN, Thomason JM, Hurdle HM, Wills RW, Fontenot RL. Effects of
Firocoxib, Flunixin Meglumine, and Phenylbutazone on Platelet Function and
Thromboxane Synthesis in Healthy Horses. Vet Surg. 2016 Nov;45(8):1087-1094. doi:
10.1111/vsu.12567. Epub 2016 Oct 12. PubMed PMID: 27731498.
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8: McRae G, Leek DM, Pagliano E. Solution to phenylbutazone purity challenge.
Anal Bioanal Chem. 2016 Sep;408(22):5957-8. doi: 10.1007/s00216-016-9706-6.
PubMed PMID: 27515929.

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9: Boison JO, Dowling T, Johnson R, Kinar J. Analysis of phenylbutazone residues
in horse tissues with and without enzyme-hydrolysis by LC-MS/MS. Drug Test Anal.
2016 May;8(5-6):535-8. doi: 10.1002/dta.2020. PubMed PMID: 27443208.
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10: 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. PubMed PMID: 27126921; PubMed
Central PMCID: PMC4850456.

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