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MedKoo Cat#: 326868 | Name: Oxyphenbutazone
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Description:

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

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

Chemical Structure

Oxyphenbutazone
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
10mg USD 250.00
25mg USD 450.00
50mg USD 750.00
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Related CAS #
No Data
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
More Info
Related CAS# 7081-38-1(Oxyphenbutazone Monohydrate) 129-20-4(Oxyphenbutazone)
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Oxyphenbutazone is a Phenylbutazone (HY-B0230) metabolite, with anti-inflammatory effect. Oxyphenbutazone is an orally active non-selective COX inhibitor.
In vitro activity:
In WB cultures, 4OH-OPB was less effective than in PBMC cultures, but was still the best inhibitor of lymphokine production and, furthermore, was the only inhibitor of monokine production. The increase in 4OH-OPB concentration needed to induce the same inhibition of cytokine production in WB as in PBMC culture could be mimicked by the addition of erythrocytes to the PBMC cultures. Experiments with radioactively-labeled 4OH-OPB suggest that 4OH-OPB is taken up very rapidly into erythrocytes and is secreted by the erythrocytes with much slower kinetics via a multidrug-resistance-associated protein. Reference: Eur Cytokine Netw. 2005 Jun;16(2):144-51. https://pubmed.ncbi.nlm.nih.gov/15941686/
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
Solubility
PBS (pH 7.2) 0.5 1.54
Water 1.0 3.08
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 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
Formulation protocol:
1. 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. PMID: 15941686. 2. 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. 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. PMID: 15941686.
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: 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.