WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H318486
CAS#: 50-33-9 (free form)
Description: 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.
Hodoodo Cat#: H318486
Name: Phenylbutazone
CAS#: 50-33-9 (free form)
Chemical Formula: C19H20N2O2
Exact Mass: 308.15
Molecular Weight: 308.381
Elemental Analysis: C, 74.00; H, 6.54; N, 9.08; O, 10.38
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
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.
| 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Knych HK, Stanley SD, Seminoff KN, McKemie DS, Kass PH. Pharmacokinetics of
methocarbamol and phenylbutazone in exercised Thoroughbred horses. J Vet
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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.
