Oxaprozin-d5 | CAS#unknown | Oxaprozin quantification internal standard

MedKoo Cat#: 464685 | Name: Oxaprozin-d5

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Description:

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

Oxaprozin-d5 is intended for use as an internal standard for the quantification of oxaprozin by GC- or LC-MS. Oxaprozin is a non-steroidal anti-inflammatory drug (NSAID) and COX inhibitor (IC50s = 2.2 and 36 μM for human COX-1 and COX-2, respectively). It decreases acetic acid-induced writhing times and carrageenan-induced paw edema in mice when administered at doses of 100 and 70 mg/kg, respectively. Formulations containing oxaprozin have been used in the treatment of pain associated with osteoarthritis and rheumatoid arthritis.

Chemical Structure

Oxaprozin-d5

CAS#unknown

Theoretical Analysis

MedKoo Cat#: 464685

Name: Oxaprozin-d5

CAS#: unknown

Chemical Formula: C18H10D5NO3

Exact Mass: 298.1366

Molecular Weight: 298.35

Elemental Analysis: C, 72.46; H, 6.75; N, 4.69; O, 16.09

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Oxaprozin-d5; Oxaprozin d5;

IUPAC/Chemical Name

3-(4-phenyl-5-(phenyl-d5)oxazol-2-yl)propanoic acid

InChi Key

OFPXSFXSNFPTHF-OUHXUHDZSA-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)/i2D,5D,6D,9D,10D

SMILES Code

OC(CCC1=NC(C2=CC=CC=C2)=C(O1)C3=C(C([2H])=C(C([2H])=C3[2H])[2H])[2H])=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

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:

Oxaprozin-d5 is deuterium labeled Oxaprozin. Oxaprozin is an inhibitor of both COX-1 and COX-2 with IC50s of 2.2 μM and 36 μM for human platelet COX-1 and 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/

Preparing Stock Solutions

The following data is based on the product molecular weight 298.35 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: Schierle S, Chaikuad A, Lillich FF, Ni X, Woltersdorf S, Schallmayer E, Renelt B, Ronchetti R, Knapp S, Proschak E, Merk D. Oxaprozin Analogues as Selective RXR Agonists with Superior Properties and Pharmacokinetics. J Med Chem. 2021 Apr 22;64(8):5123-5136. doi: 10.1021/acs.jmedchem.1c00235. Epub 2021 Apr 1. PMID: 33793232. 2: Park KC, Dharmasivam M, Richardson DR. The Role of Extracellular Proteases in Tumor Progression and the Development of Innovative Metal Ion Chelators that Inhibit their Activity. Int J Mol Sci. 2020 Sep 16;21(18):6805. doi: 10.3390/ijms21186805. PMID: 32948029; PMCID: PMC7555822. 3: Forgács V, Németh E, Gyuricza B, Kis A, Szabó JP, Mikecz P, Mátyus P, Helyes Z, Horváth ÁI, Kálai T, Trencsényi G, Fekete A, Szikra D. Radiosynthesis and Preclinical Investigation of 11 C-Labelled 3-(4,5-Diphenyl-1,3-oxazol-2-yl)propanal Oxime ([11 C]SZV 1287). ChemMedChem. 2020 Dec 15;15(24):2470-2476. doi: 10.1002/cmdc.202000389. Epub 2020 Oct 22. PMID: 32935925. 4: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Oxaprozin. 2020 Mar 20. PMID: 31643656. 5: Furihata K, Nagasawa K, Hagino A, Kumagai Y. A drug-drug interaction study of a novel, selective urate reabsorption inhibitor dotinurad and the non-steroidal anti-inflammatory drug oxaprozin in healthy adult males. Clin Exp Nephrol. 2020 Mar;24(Suppl 1):36-43. doi: 10.1007/s10157-020-01855-2. Epub 2020 Feb 19. PMID: 32076889; PMCID: PMC7066271. 6: Dimiza F, Lazou M, Papadopoulos AN, Hatzidimitriou AG, Psomas G. Manganese(II) coordination compounds of carboxylate non-steroidal anti- inflammatory drugs. J Inorg Biochem. 2020 Feb;203:110906. doi: 10.1016/j.jinorgbio.2019.110906. Epub 2019 Oct 25. PMID: 31707332. 7: Epstein NE. When to stop anticoagulation, anti-platelet aggregates, and non- steroidal anti-inflammatories (NSAIDs) prior to spine surgery. Surg Neurol Int. 2019 Mar 26;10:45. doi: 10.25259/SNI-54-2019. PMID: 31528383; PMCID: PMC6743676. 8: Mishra R, Rana S. A rational search for discovering potential neutraligands of human complement fragment 5a (hC5a). Bioorg Med Chem. 2019 Oct 1;27(19):115052. doi: 10.1016/j.bmc.2019.115052. Epub 2019 Aug 19. PMID: 31447248. 9: Liu S, Bao X, Zhang S, Zhang H, Lu X, Li T, Chen Z, Chen N. The study of ultrasound and iontophoresis on oxaprozin transdermal penetration using surface- enhanced Raman spectroscopy. Drug Deliv Transl Res. 2020 Feb;10(1):83-92. doi: 10.1007/s13346-019-00664-9. PMID: 31407271. 10: Sharma V, Bhatia P, Alam O, Javed Naim M, Nawaz F, Ahmad Sheikh A, Jha M. Recent advancement in the discovery and development of COX-2 inhibitors: Insight into biological activities and SAR studies (2008-2019). Bioorg Chem. 2019 Aug;89:103007. doi: 10.1016/j.bioorg.2019.103007. Epub 2019 May 21. PMID: 31132600. 11: Lazou M, Hatzidimitriou AG, Papadopoulos AN, Psomas G. Zinc-oxaprozin compounds: Synthesis, structure and biological activity. J Inorg Biochem. 2019 Jun;195:101-110. doi: 10.1016/j.jinorgbio.2019.03.016. Epub 2019 Mar 21. PMID: 30939377. 12: Ianni A, Celenza G, Franceschini N. Oxaprozin: A new hope in the modulation of matrix metalloproteinase 9 activity. Chem Biol Drug Des. 2019 May;93(5):811-817. doi: 10.1111/cbdd.13468. Epub 2019 Jan 11. PMID: 30582279. 13: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Oxaprozin. 2018 Oct 31. PMID: 30000217. 14: Li CW, Chen BS. Investigating HIV-Human Interaction Networks to Unravel Pathogenic Mechanism for Drug Discovery: A Systems Biology Approach. Curr HIV Res. 2018;16(1):77-95. doi: 10.2174/1570162X16666180219155324. PMID: 29468972. 15: Peesa JP, Atmakuri LR, Yalavarthi PR, Mandava Venkata BR, Rasheed A, Pachava V. Oxaprozin prodrug as safer nonsteroidal anti-inflammatory drug: Synthesis and pharmacological evaluation. Arch Pharm (Weinheim). 2018 Feb;351(2). doi: 10.1002/ardp.201700256. Epub 2017 Dec 28. PMID: 29283449. 16: Maestrelli F, Mura P, Cirri M, Mennini N, Ghelardini C, Di Cesare Mannelli L. Development and characterization of fast dissolving tablets of oxaprozin based on hybrid systems of the drug with cyclodextrins and nanoclays. Int J Pharm. 2017 Oct 15;531(2):640-649. doi: 10.1016/j.ijpharm.2017.05.033. Epub 2017 May 15. PMID: 28522425. 17: Mennini N, Cirri M, Maestrelli F, Mura P. Comparison of liposomal and NLC (nanostructured lipid carrier) formulations for improving the transdermal delivery of oxaprozin: Effect of cyclodextrin complexation. Int J Pharm. 2016 Dec 30;515(1-2):684-691. doi: 10.1016/j.ijpharm.2016.11.013. Epub 2016 Nov 5. PMID: 27825863. 18: Patil PC, Luzzio FA. Synthesis of Extended Oxazoles III: Reactions of 2-(Phenylsulfonyl)methyl-4,5-diaryloxazoles. J Org Chem. 2016 Nov 4;81(21):10521-10526. doi: 10.1021/acs.joc.6b01280. Epub 2016 Aug 4. PMID: 27441569. 19: Mennini N, Maestrelli F, Cirri M, Mura P. Analysis of physicochemical properties of ternary systems of oxaprozin with randomly methylated-ß- cyclodextrin and l-arginine aimed to improve the drug solubility. J Pharm Biomed Anal. 2016 Sep 10;129:350-358. doi: 10.1016/j.jpba.2016.07.024. Epub 2016 Jul 18. PMID: 27454086. 20: 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 Jul 25;509(1-2):8-15. doi: 10.1016/j.ijpharm.2016.05.028. Epub 2016 May 14. PMID: 27188644.