Phenylbutazone-d9 | CAS#1189479-75-1 | Phenylbutazone internal standard

Phenylbutazone-d9
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 464698

CAS#: 1189479-75-1

Description: 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

CAS# 1189479-75-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464698
Name: Phenylbutazone-d9
CAS#: 1189479-75-1
Chemical Formula: C19H11D9N2O2
Exact Mass: 317.21
Molecular Weight: 317.436
Elemental Analysis: C, 71.89; H, 9.20; N, 8.83; O, 10.08

Price and Availability

Size	Price	Availability
10mg	USD -2	2 Weeks
25mg	USD -2	2 Weeks
50mg	USD -2	2 Weeks
100mg	USD -2	2 Weeks
200mg	USD -2	2 Weeks
500mg	USD -2	2 Weeks
2g	USD -2	2 Weeks
1mg	USD 340	2 Weeks
5mg	USD 840	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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.

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.

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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.

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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.

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