MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 464698 | Name: Phenylbutazone-d9
Featured

Description:

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

Phenylbutazone-d9 is intended for use as an internal standard for the quantification of phenylbutazone by GC- or LC-MS. Phenylbutazone is a non-steroidal anti-inflammatory drug and an inhibitor of the peroxidase activity of COX (IC50 = ~100 µM in the presence of hydrogen peroxide). It also inhibits prostaglandin I synthase (IC50 = ~25 µM in the presence of hydrogen peroxide). Phenylbutazone (2 mg/kg) reduces increases in type II collagen levels in the inflamed joints of an equine model of LPS-induced acute synovitis. Formulations containing phenylbutazone have been used in the treatment of lameness in horses.

Chemical Structure

Phenylbutazone-d9
Phenylbutazone-d9
CAS#1189479-75-1

Theoretical Analysis

MedKoo Cat#: 464698

Name: Phenylbutazone-d9

CAS#: 1189479-75-1

Chemical Formula: C19H11D9N2O2

Exact Mass: 317.2090

Molecular Weight: 317.44

Elemental Analysis: C, 71.89; H, 9.20; N, 8.83; O, 10.08

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
5mg USD 950.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Phenylbutazone-d9; Phenylbutazone d9;
IUPAC/Chemical Name
4-(butyl-d9)-1,2-diphenylpyrazolidine-3,5-dione
InChi Key
VYMDGNCVAMGZFE-ABVHXWLASA-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/i1D3,2D2,3D2,14D2
SMILES Code
O=C1C(C(N(N1C2=CC=CC=C2)C3=CC=CC=C3)=O)C([2H])(C([2H])(C([2H])(C([2H])([2H])[2H])[2H])[2H])[2H]
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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-d9 is the deuterium labeled Phenylbutazone. Phenylbutazone is an efficient reducing cofactor for the peroxidase activity of prostaglandin H synthase (PHS). Phenylbutazone, a hepatotoxin, is a nonsteroidal anti-inflammatory agent (NSAID).
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 317.44 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: Banerjee S, Butcher R. Pharmacological Interventions for Chronic Pain in Pediatric Patients: A Review of Guidelines [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2020 May 5. PMID: 33119240. 2: Faria JV, Vegi PF, Miguita AGC, Dos Santos MS, Boechat N, Bernardino AMR. Recently reported biological activities of pyrazole compounds. Bioorg Med Chem. 2017 Nov 1;25(21):5891-5903. doi: 10.1016/j.bmc.2017.09.035. Epub 2017 Sep 23. PMID: 28988624. 3: Baynes RE, Dedonder K, Kissell L, Mzyk D, Marmulak T, Smith G, Tell L, Gehring R, Davis J, Riviere JE. Health concerns and management of select veterinary drug residues. Food Chem Toxicol. 2016 Feb;88:112-22. doi: 10.1016/j.fct.2015.12.020. Epub 2016 Jan 2. PMID: 26751035. 4: Sanchez LC, Robertson SA. Pain control in horses: what do we really know? Equine Vet J. 2014 Jul;46(4):517-23. doi: 10.1111/evj.12265. Epub 2014 May 15. PMID: 24645799. 5: Combes RD. Is phenylbutazone a genotoxic carcinogen? A weight-of-evidence assessment. Altern Lab Anim. 2013 Jul;41(3):235-48. doi: 10.1177/026119291304100307. PMID: 23971704. 6: 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. PMID: 23721873. 7: Brooks KG, Thompson DF. A review and assessment of drug-induced parotitis. Ann Pharmacother. 2012 Dec;46(12):1688-99. doi: 10.1345/aph.1R228. Epub 2012 Dec 18. PMID: 23249870. 8: Weiss DJ. Drug-associated blood cell dyscrasias. Compend Contin Educ Vet. 2012 Jun;34(6):E2. PMID: 22692675. 9: Gigante A, Tagarro I. Non-steroidal anti-inflammatory drugs and gastroprotection with proton pump inhibitors: a focus on ketoprofen/omeprazole. Clin Drug Investig. 2012 Apr 1;32(4):221-33. doi: 10.2165/11596670-000000000-00000. PMID: 22350497. 10: Ramiro S, Radner H, van der Heijde D, van Tubergen A, Buchbinder R, Aletaha D, Landewé RB. Combination therapy for pain management in inflammatory arthritis (rheumatoid arthritis, ankylosing spondylitis, psoriatic arthritis, other spondyloarthritis). Cochrane Database Syst Rev. 2011 Oct 5;(10):CD008886. doi: 10.1002/14651858.CD008886.pub2. PMID: 21975788. 11: 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. PMID: 21668837. 12: Benet LZ. Clearance (née Rowland) concepts: a downdate and an update. J Pharmacokinet Pharmacodyn. 2010 Dec;37(6):529-39. doi: 10.1007/s10928-010-9187-8. Epub 2010 Nov 27. PMID: 21113650; PMCID: PMC3005114. 13: Maciazek-Jurczyk M, Sułkowska A, Bojko B, Równicka-Zubik J, Sułkowski WW. Interaction of phenylbutazone and colchicine in binding to serum albumin in rheumatoid therapy: 1H NMR study. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Sep 15;74(1):1-9. doi: 10.1016/j.saa.2009.06.043. Epub 2009 Jun 25. Erratum in: Spectrochim Acta A Mol Biomol Spectrosc. 2010 Apr;75(4):1380. PMID: 19615934. 14: Papich MG. An update on nonsteroidal anti-inflammatory drugs (NSAIDs) in small animals. Vet Clin North Am Small Anim Pract. 2008 Nov;38(6):1243-66, vi. doi: 10.1016/j.cvsm.2008.09.002. PMID: 18954683. 15: Rainsford KD. Anti-inflammatory drugs in the 21st century. Subcell Biochem. 2007;42:3-27. doi: 10.1007/1-4020-5688-5_1. PMID: 17612044. 16: Muraoka S, Miura T. [Metabolism of non-steroidal anti-inflammatory drugs by peroxidase: implication for gastrointestinal mucosal lesions]. Yakugaku Zasshi. 2007 Apr;127(4):749-56. Japanese. doi: 10.1248/yakushi.127.749. PMID: 17409707. 17: Hawrot-Kawecka AM, Kawecki GP, Duława J. Hiperamonemia typu ii jako przykład choroby cyklu mocznikowego [Hyperammonemia type II as an example of urea cycle disorder]. Wiad Lek. 2006;59(7-8):512-5. Polish. PMID: 17209350. 18: Goodrich LR, Nixon AJ. Medical treatment of osteoarthritis in the horse - a review. Vet J. 2006 Jan;171(1):51-69. doi: 10.1016/j.tvjl.2004.07.008. PMID: 16427582. 19: Lees P, Giraudel J, Landoni MF, Toutain PL. PK-PD integration and PK-PD modelling of nonsteroidal anti-inflammatory drugs: principles and applications in veterinary pharmacology. J Vet Pharmacol Ther. 2004 Dec;27(6):491-502. doi: 10.1111/j.1365-2885.2004.00618.x. PMID: 15601443. 20: Niki I. [Contribution of diabetic research to versatile strategies for the treatment of diabetes mellitus]. Nihon Yakurigaku Zasshi. 2003 Sep;122(3):228-35. Japanese. doi: 10.1254/fpj.122.228. PMID: 12939540.