Oxaprozin - CAS 21256-18-8
Catalog number: 21256-18-8
Category: Inhibitor
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Molecular Formula:
C18H15NO3
Molecular Weight:
293.32
COA:
Inquire
Targets:
Cox-2
Description:
A inhibitor of both COX-1 and COX-2
Brife Description:
A inhibitor of both COX-1 and COX-2
Appearance:
White Solid
Synonyms:
4,5-diphenyl-2-oxazolepropionic acid; Apo-Oxaprozin; Danoprox; Daypro; Dayrun; Rhoxal-oxaprozin ; Wy-21,743
Solubility:
DMSO 59 mg/mL (201.14 mM); Ethanol 27 mg/mL (92.04 mM)
Storage:
3 years -20°C powder;6 months-80°C in solvent
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Grams-Kilos
Boiling Point:
467°C at 760 mmHg
Melting Point:
158-159°C
InChIKey:
OFPXSFXSNFPTHF-UHFFFAOYSA-N
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)
Canonical SMILES:
C1=CC=C(C=C1)C2=C(OC(=N2)CCC(=O)O)C3=CC=CC=C3
1.Oxaprozin-Loaded Lipid Nanoparticles towards Overcoming NSAIDs Side-Effects.
Lopes-de-Araújo J1, Neves AR1, Gouveia VM1, Moura CC1, Nunes C2, Reis S1. Pharm Res. 2016 Feb;33(2):301-14. doi: 10.1007/s11095-015-1788-x. Epub 2015 Sep 9.
PURPOSE: Nanostructured Lipid Carriers (NLCs) loading oxaprozin were developed to address an effective drug packaging and targeted delivery, improving the drug pharmacokinetics and pharmacodynamics properties and avoiding the local gastric side-effects. Macrophages actively phagocyte particles with sizes larger than 200 nm and, when activated, over-express folate beta receptors - features that in the case of this work constitute the basis for passive and active targeting strategies.
2.Synthesis of extended oxazoles II: Reaction manifold of 2-(halomethyl)-4,5-diaryloxazoles.
Patil PC1, Luzzio FA1. Tetrahedron Lett. 2016 Feb 17;57(7):757-759.
2-(Halomethyl)-4,5-diphenyloxazoles are effective, reactive scaffolds which can be utilized for synthetic elaboration at the 2-position. Through substitution reactions, the chloromethyl analogue is used to prepare a number of 2-alkylamino-, 2-alkylthio- and 2-alkoxy-(methyl) oxazoles. The 2-bromomethyl analogue offers a more reactive alternative to the chloromethyl compounds and is useful in the C-alkylation of a stabilized (malonate) carbanion as exemplified by a concise synthesis of Oxaprozin.
3.Drug/drug interaction of common NSAIDs with antiplatelet effect of aspirin in human platelets.
Saxena A1, Balaramnavar VM, Hohlfeld T, Saxena AK. Eur J Pharmacol. 2013 Dec 5;721(1-3):215-24. doi: 10.1016/j.ejphar.2013.09.032. Epub 2013 Sep 25.
Nonsteroidal anti-inflammatory drugs (NSAIDs) may interfere with the anti-platelet activity of aspirin at the level of the platelet cyclooxygenase-1 (COX-1) enzyme. In order to examine the interference of common NSAIDs with the anti-platelet activity of aspirin the human platelet rich plasma from voluntary donors was used for arachidonic acid-induced aggregation and determination of thromboxane synthesis. Further, docking studies were used to explain the molecular basis of the NSAID/aspirin interaction. The experimental results showed that celecoxib, dipyrone (active metabolite), ibuprofen, flufenamic acid, naproxen, nimesulide, oxaprozin, and piroxicam significantly interfere with the anti-platelet activity of aspirin, while diclofenac, ketorolac and acetaminophen do not. Docking studies suggested that NSAIDs forming hydrogen bonds with Ser530, Arg120, Tyr385 and other amino acids of the COX-1 hydrophobic channel interfere with antiplatelet activity of aspirin while non interfering NSAIDs do not form relevant hydrogen bond interactions within the aspirin binding site.
4.Theoretical and vibrational studies of 4,5-diphenyl-2-2 oxazole propionic acid (oxaprozin).
Sagdinc SG1, Esme A. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Apr;75(4):1370-6. doi: 10.1016/j.saa.2010.01.004. Epub 2010 Feb 1.
The molecular structure, linear and nonlinear optical properties, and electronic properties of 4,5-diphenyl-2-2 oxazole propionic acid (oxaprozin) as a monomer were investigated by using Hartree-Fock (HF) and density functional theory (DFT) calculations that used 6-31G(d,p) basis set. The first-order hyperpolarizability of oxaprozin (OXA) was found to be 1.117 x 10(-30) esu. The structure of oxaprozin dimer with HF/6-31G(d) level caused by the shifts of O-H and CO bands in the vibrational spectra of oxaprozin were also studied. Moreover, these calculated frequencies of oxaprozin dimer were compared with the solid FT-IR and FT-Raman spectra. The theoretical frequencies and infrared intensities were showed a good agreement with experimental data.
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CAS 21256-18-8 Oxaprozin

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