Oxyphenbutazone
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MedKoo CAT#: 326868

CAS#: 129-20-4

Description: Oxyphenbutazone, also known as G-29701, a non-steroidal anti-inflammatory drug (NSAID). It is a metabolite of phenylbutazone.


Chemical Structure

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Oxyphenbutazone
CAS# 129-20-4

Theoretical Analysis

MedKoo Cat#: 326868
Name: Oxyphenbutazone
CAS#: 129-20-4
Chemical Formula: C19H20N2O3
Exact Mass: 324.1474
Molecular Weight: 324.38
Elemental Analysis: C, 70.35; H, 6.21; N, 8.64; O, 14.80

Price and Availability

Size Price Availability Quantity
10.0mg USD 250.0 2 Weeks
25.0mg USD 450.0 2 Weeks
50.0mg USD 750.0 2 Weeks
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Synonym: G-29701; G29701; G 29701. Oxyphenbutazone

IUPAC/Chemical Name: 4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione

InChi Key: HFHZKZSRXITVMK-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3

SMILES Code: O=C(C1CCCC)N(C2=CC=CC=C2)N(C3=CC=C(O)C=C3)C1=O

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 324.38 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

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1: Kapadia GJ, Azuine MA, Shigeta Y, Suzuki N, Tokuda H. Chemopreventive activities of etodolac and oxyphenbutazone against mouse skin carcinogenesis. Bioorg Med Chem Lett. 2010 Apr 15;20(8):2546-8. doi: 10.1016/j.bmcl.2010.02.093. Epub 2010 Mar 1. PubMed PMID: 20299217.

2: You Y, Uboh CE, Soma LR, Guan F, Li X, Rudy JA, Chen J. Screening, quantification, and confirmation of phenylbutazone and oxyphenbutazone in equine plasma by liquid chromatography-tandem mass spectrometry. J Anal Toxicol. 2009 Jan-Feb;33(1):41-50. PubMed PMID: 19161668.

3: Ten Brinke A, Dekkers DW, Notten SM, Karsten ML, de Groot ER, Aarden LA. 4-Hydroxy-oxyphenbutazone is a potent inhibitor of cytokine production. Eur Cytokine Netw. 2005 Jun;16(2):144-51. PubMed PMID: 15941686.

4: Singh N, Jabeen T, Somvanshi RK, Sharma S, Dey S, Singh TP. Phospholipase A2 as a target protein for nonsteroidal anti-inflammatory drugs (NSAIDS): crystal structure of the complex formed between phospholipase A2 and oxyphenbutazone at 1.6 A resolution. Biochemistry. 2004 Nov 23;43(46):14577-83. PubMed PMID: 15544328.

5: Veiga MD, Merino M. Interactions of oxyphenbutazone with different cyclodextrins in aqueous medium and in the solid state. J Pharm Biomed Anal. 2002 Jun 1;28(5):973-82. PubMed PMID: 12039640.

6: Matthews NS, Peck KE, Taylor TS, Mealey KL. Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys. Am J Vet Res. 2001 May;62(5):673-5. PubMed PMID: 11341383.

7: Grippa E, Santini L, Castellano G, Gatto MT, Leone MG, Saso L. Simultaneous determination of hydrocortisone, dexamethasone, indomethacin, phenylbutazone and oxyphenbutazone in equine serum by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 2000 Jan 28;738(1):17-25. PubMed PMID: 10778922.

8: Razdan B, Nagaraj NV. Evaluation of dosage forms. VI. Studies of commercial oxyphenbutazone tablet dosage forms. Drug Dev Ind Pharm. 1999 Sep;25(9):1051-6. Erratum in: Drug Dev Ind Pharm. 2000 Oct;26(10):1129. PubMed PMID: 10518246.

9: Cheng Z, Welsh E, Nolan A, McKellar QA. Pharmacokinetic and pharmacodynamic studies on phenylbutazone and oxyphenbutazone in goats. Vet Rec. 1997 Jan 11;140(2):40-3. PubMed PMID: 9123796.

10: Mealey KL, Matthews NS, Peck KE, Ray AC, Taylor TS. Comparative pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in clinically normal horses and donkeys. Am J Vet Res. 1997 Jan;58(1):53-5. PubMed PMID: 8989496.

11: Neto LM, Andraus MH, Salvadori MC. Determination of phenylbutazone and oxyphenbutazone in plasma and urine samples of horses by high-performance liquid chromatography and gas chromatography-mass spectrometry. J Chromatogr B Biomed Appl. 1996 Apr 12;678(2):211-8. PubMed PMID: 8738024.

12: Cheng Z, McKellar QA, Nolan A, Lees P. Pharmacokinetics and pharmacodynamics of phenylbutazone and oxyphenbutazone in the donkey. J Vet Pharmacol Ther. 1996 Apr;19(2):149-51. PubMed PMID: 8735424.

13: Simmons BR, Jagota NK, Stewart JT. A supercritical fluid chromatographic method using packed columns for phenylbutazone and oxyphenbutazone in serum, and for phenylbutazone in a dosage form. J Pharm Biomed Anal. 1995 Jan;13(1):59-64. PubMed PMID: 7718635.

14: Saeed A, Haque S, Qureshi SZ. Resin bead detection and spectrophotometric determination of oxyphenbutazone with p-dimethylaminocinnamaldehyde: Application to bulk drug and dosage forms. Talanta. 1993 Dec;40(12):1867-71. PubMed PMID: 18965864.

15: Caturla MC, Cusido E. Solid-phase extraction for the high-performance liquid chromatographic determination of indomethacin, suxibuzone, phenylbutazone and oxyphenbutazone in plasma, avoiding degradation of compounds. J Chromatogr. 1992 Oct 2;581(1):101-7. PubMed PMID: 1429991.

16: Crisman MV, Wilcke JR, Sams RA, Gerken DF. Concentrations of phenylbutazone and oxyphenbutazone in post-parturient mares and their neonatal foals. J Vet Pharmacol Ther. 1991 Sep;14(3):330-4. PubMed PMID: 1744942.

17: Stoltz M, Oliver DW, Wessels PL, Chalmers AA. High-resolution solid-state carbon-13 nuclear magnetic resonance spectra of mofebutazone, phenylbutazone, and oxyphenbutazone in relation to X-ray crystallographic data. J Pharm Sci. 1991 Apr;80(4):357-62. PubMed PMID: 1865336.

18: Cameli N, Vincenzi C, Morelli R, Bardazzi F, Tardio M. Contact allergy to oxyphenbutazone. Contact Dermatitis. 1991 Jan;24(1):75-6. PubMed PMID: 2044383.

19: D'Souza RS, Bhounsule SA, Dhume VG. Comparison of the effects of captopril and enalapril on oxyphenbutazone and ethanol-induced gastric lesions in rats. Indian J Physiol Pharmacol. 1990 Jul;34(3):206-8. PubMed PMID: 2286425.

20: Bhounsule SA, Pereira JS, Hede SS, Diniz D'Souza RS. Effect of captopril on oxyphenbutazone and ethanol-induced gastric lesions in rats. Eur J Pharmacol. 1990 Feb 20;177(1-2):87-90. PubMed PMID: 2187703.



Additional Information

Related CAS#
7081-38-1(Oxyphenbutazone Monohydrate)
129-20-4(Oxyphenbutazone)