Oxaprozin | CAS#21256-18-8

MedKoo Cat#: 318396 | Name: Oxaprozin

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Description:

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

Oxaprozin is a non-steroidal anti-inflammatory drug (NSAID), used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis. Chemically, it is a propionic acid derivative.

Chemical Structure

Oxaprozin

CAS#21256-18-8

Theoretical Analysis

MedKoo Cat#: 318396

Name: Oxaprozin

CAS#: 21256-18-8

Chemical Formula: C18H15NO3

Exact Mass: 293.1052

Molecular Weight: 293.32

Elemental Analysis: C, 73.71; H, 5.15; N, 4.78; O, 16.36

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
5g	USD 750.00	2 Weeks
10g	USD 1,250.00	2 Weeks

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Synonym

Oxaprozin, Oxaprozinum, DL-8280, DR-3355, Hoe-280, ORF-28489, Ru-43280, Tarivid

IUPAC/Chemical Name

4,5-Diphenyl-2-oxazolepropanoic acid

InChi Key

OFPXSFXSNFPTHF-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)

SMILES Code

O=C(O)CCC1=NC(C2=CC=CC=C2)=C(C3=CC=CC=C3)O1

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxaprozin is an orally active and potent COX inhibitor, with IC50 values of 2.2 μM for human platelet COX-1 and and 36 μM for IL-1-stimulated human synovial cell COX-2.

In vitro activity:

Oxaprozin reversed in a dose-dependent manner immune complex-induced survival of monocytes, without affecting the apoptosis of resting cells. Other NSAIDs are ineffective. The activity of oxaprozin was related to inhibition of Akt activation that, in turn, prevented p38 MAPK, IKK and NF-kappaB activation. Reference: Br J Pharmacol. 2009 May;157(2):294-306. https://pubmed.ncbi.nlm.nih.gov/19338579/

In vivo activity:

The effect of oxaprozin (OXP) on an experimental model of seizures in rats was investigated in this study. Intraperitoneal injection of OXP increased the mean latency of myoclonic jerks and generalized tonic-clonic seizure (GTCS) and decreased the number of myoclonic jerks and GTCS duration compared with the PTZ group. Biochemical tests showed that pretreatment with OXP was able to restore GSH serum levels and reverse the augmented NO serum levels caused by PTZ induction to the normal level. The quantitative polymerase chain reaction results also revealed that OXP counteracts the negative effects of PTZ by affecting the expression of the Sirt1 and Pgc1α genes. Reference: Can J Physiol Pharmacol. 2022 Jun 1;100(6):534-541. https://pubmed.ncbi.nlm.nih.gov/35395161/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	102.28
	DMSO	62.7	213.64
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.70
	Ethanol	36.5	124.44

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 293.32 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. Montecucco F, Bertolotto M, Ottonello L, Quercioli A, Mach F, Dallegri F. Oxaprozin-induced apoptosis on CD40 ligand-treated human primary monocytes is associated with the modulation of defined intracellular pathways. J Biomed Biotechnol. 2009;2009:478785. doi: 10.1155/2009/478785. Epub 2009 Aug 10. PMID: 19672323; PMCID: PMC2723963. 2. Ottonello L, Bertolotto M, Montecucco F, Bianchi G, Dallegri F. Delayed apoptosis of human monocytes exposed to immune complexes is reversed by oxaprozin: role of the Akt/IkappaB kinase/nuclear factor kappaB pathway. Br J Pharmacol. 2009 May;157(2):294-306. doi: 10.1111/j.1476-5381.2009.00162.x. Epub 2009 Mar 26. PMID: 19338579; PMCID: PMC2697812. 3. Khatami P, Mirazi N, Khosravi M, Bananej M. Anticonvulsant activity of oxaprozin in a rat model of pentylenetetrazole-induced seizure by targeting oxidative stress and SIRT1/PGC1α signaling. Can J Physiol Pharmacol. 2022 Jun 1;100(6):534-541. doi: 10.1139/cjpp-2021-0757. Epub 2022 Apr 8. PMID: 35395161. 4. Goto J, Muramatsu M, Hosoda K, Otomo S, Aihara H. [The inhibitory effect of oxaprozin, a new non-steroidal anti-inflammatory drug, on platelet aggregation]. Nihon Yakurigaku Zasshi. 1984 May;83(5):395-400. Japanese. PMID: 6432657.

In vitro protocol:

In vivo protocol:

1. Khatami P, Mirazi N, Khosravi M, Bananej M. Anticonvulsant activity of oxaprozin in a rat model of pentylenetetrazole-induced seizure by targeting oxidative stress and SIRT1/PGC1α signaling. Can J Physiol Pharmacol. 2022 Jun 1;100(6):534-541. doi: 10.1139/cjpp-2021-0757. Epub 2022 Apr 8. PMID: 35395161. 2. Goto J, Muramatsu M, Hosoda K, Otomo S, Aihara H. [The inhibitory effect of oxaprozin, a new non-steroidal anti-inflammatory drug, on platelet aggregation]. Nihon Yakurigaku Zasshi. 1984 May;83(5):395-400. Japanese. PMID: 6432657.

1: Mura P, Maestrelli F, Aguzzi C, Viseras C. Hybrid systems based on "drug - in cyclodextrin - in nanoclays" for improving oxaprozin dissolution properties. Int J Pharm. 2016 May 14;509(1-2):8-15. doi: 10.1016/j.ijpharm.2016.05.028. [Epub ahead of print] PubMed PMID: 27188644. 2: Lopes-de-Araújo J, Neves AR, Gouveia VM, Moura CC, Nunes C, Reis S. Oxaprozin-Loaded Lipid Nanoparticles towards Overcoming NSAIDs Side-Effects. Pharm Res. 2016 Feb;33(2):301-14. doi: 10.1007/s11095-015-1788-x. Epub 2015 Sep 9. PubMed PMID: 26350105. 3: Mao M, Wang L, Jiang X, Yang L. [Determination of oxaprozin in human plasma with high performance liquid chromatography (HPLC) and its application]. Sheng Wu Yi Xue Gong Cheng Xue Za Zhi. 2013 Jun;30(3):646-50. Chinese. PubMed PMID: 23865335. 4: Božić BD, Rogan JR, Poleti DD, Trišović NP, Božić BD, Ušćumlić GS. Synthesis, characterization and antiproliferative activity of transition metal complexes with 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid (oxaprozin). Chem Pharm Bull (Tokyo). 2012;60(7):865-9. PubMed PMID: 22790819. 5: Maestrelli F, Cirri M, Mennini N, Zerrouk N, Mura P. Improvement of oxaprozin solubility and permeability by the combined use of cyclodextrin, chitosan, and bile components. Eur J Pharm Biopharm. 2011 Aug;78(3):385-93. doi: 10.1016/j.ejpb.2011.03.012. Epub 2011 Mar 23. PubMed PMID: 21439375. 6: Kara IM, Polat S, Inci MF, Gümüş C. Analgesic and anti-inflammatory effects of oxaprozin and naproxen sodium after removal of impacted lower third molars: a randomized, double-blind, placebo-controlled crossover study. J Oral Maxillofac Surg. 2010 May;68(5):1018-24. doi: 10.1016/j.joms.2009.09.094. Epub 2010 Mar 5. Erratum in: J Oral Maxillofac Surg. 2010 Aug;68(8):2036. J Oral Maxillofac Surg. 2011 Dec;69(12):3051. Ince, Fatih [corrected to Inci, M Fatih]. PubMed PMID: 20206429. 7: Sagdinc SG, Esme A. Theoretical and vibrational studies of 4,5-diphenyl-2-2 oxazole propionic acid (oxaprozin). Spectrochim Acta A Mol Biomol Spectrosc. 2010 Apr;75(4):1370-6. doi: 10.1016/j.saa.2010.01.004. Epub 2010 Feb 1. PubMed PMID: 20167532. 8: Montecucco F, Bertolotto M, Ottonello L, Quercioli A, Mach F, Dallegri F. Oxaprozin-induced apoptosis on CD40 ligand-treated human primary monocytes is associated with the modulation of defined intracellular pathways. J Biomed Biotechnol. 2009;2009:478785. doi: 10.1155/2009/478785. Epub 2009 Aug 10. PubMed PMID: 19672323; PubMed Central PMCID: PMC2723963. 9: Ottonello L, Bertolotto M, Montecucco F, Bianchi G, Dallegri F. Delayed apoptosis of human monocytes exposed to immune complexes is reversed by oxaprozin: role of the Akt/IkappaB kinase/nuclear factor kappaB pathway. Br J Pharmacol. 2009 May;157(2):294-306. doi: 10.1111/j.1476-5381.2009.00162.x. Epub 2009 Mar 26. PubMed PMID: 19338579; PubMed Central PMCID: PMC2697812. 10: Sun SF, Zhou B, Hou HN, Liu Y, Xiang GY. Studies on the interaction between Oxaprozin-E and bovine serum albumin by spectroscopic methods. Int J Biol Macromol. 2006 Nov 15;39(4-5):197-200. Epub 2006 Mar 28. PubMed PMID: 16828154. 11: Dallegri F, Bertolotto M, Ottonello L. A review of the emerging profile of the anti-inflammatory drug oxaprozin. Expert Opin Pharmacother. 2005 May;6(5):777-85. Review. PubMed PMID: 15934904. 12: Brinker A, Nourjah P. Patient characteristics associated with outpatient prescriptions for nabumetone and oxaprozin versus celecoxib and rofecoxib. Am J Health Syst Pharm. 2005 Apr 1;62(7):739-43. PubMed PMID: 15790802. 13: Heller B, Tarricone R. Oxaprozin versus diclofenac in NSAID-refractory periarthritis pain of the shoulder. Curr Med Res Opin. 2004 Aug;20(8):1279-90. PubMed PMID: 15324531. 14: Kean WF. Oxaprozin: kinetic and dynamic profile in the treatment of pain. Curr Med Res Opin. 2004 Aug;20(8):1275-7. PubMed PMID: 15324530. 15: Brinker A, Goldkind L, Bonnel R, Beitz J. Spontaneous reports of hypertension leading to hospitalisation in association with rofecoxib, celecoxib, nabumetone and oxaprozin. Drugs Aging. 2004;21(7):479-84. PubMed PMID: 15132714. 16: Bucolo C, Maltese A. Pharmacological profile of oxaprozin eye drops. J Ocul Pharmacol Ther. 2002 Feb;18(1):75-81. PubMed PMID: 11858617. 17: Reddy KV, Rao DS, Vyas K, Reddy GO. LC method for the quantitative determination of oxaprozin and its impurities in the bulk drug. J Pharm Biomed Anal. 2000 May;22(4):651-9. PubMed PMID: 10768354. 18: Kethu SR, Rukkannagari S, Lansford CL. Oxaprozin-induced symptomatic hepatotoxicity. Ann Pharmacother. 1999 Sep;33(9):942-4. PubMed PMID: 10492496. 19: Marland A, Sarkar P, Leavitt R, Lee-Ruff E, Ramnauth J. The elimination profiles of oxaprozin in equine urine and serum after a 4.8-g dose. J Anal Toxicol. 1999 Jul-Aug;23(4):242-6. PubMed PMID: 10445486. 20: Carucci JA, Cohen DE. Toxic epidermal necrolysis following treatment with oxaprozin. Int J Dermatol. 1999 Mar;38(3):233-4. PubMed PMID: 10208628.