Oxaprozin

Base Information

• Chemical Name: Oxaprozin
• CAS No.: 21256-18-8
• Molecular Formula: C18H15NO3
• Molecular Weight: 293.322
• Hs Code.: 29349990
• European Community (EC) Number: 244-296-1
• NSC Number: 758949,310839
• UNII: MHJ80W9LRB
• DSSTox Substance ID: DTXSID1045118
• Nikkaji Number: J10.781F
• Wikipedia: Oxaprozin
• Wikidata: Q1749609
• NCI Thesaurus Code: C29307
• RXCUI: 32613
• Pharos Ligand ID: GVRKKRTS74UJ
• Metabolomics Workbench ID: 43240
• ChEMBL ID: CHEMBL1071
• Mol file: 21256-18-8.mol

Synonyms:4,5 Diphenyl 2 oxazolepropionic Acid;4,5-diphenyl-2-oxazolepropionic acid;Apo Oxaprozin;Apo-Oxaprozin;Danoprox;Daypro;Dayrun;oxaprozin;Rhoxal oxaprozin;Rhoxal-oxaprozin;Wy 21,743;Wy-21,743

Chemical Property of Oxaprozin

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1.6E-09mmHg at 25°C
• Melting Point: 154 °C
• Refractive Index: 1.595
• Boiling Point: 467 °C at 760 mmHg
• PKA: 4.3(at 25℃)
• Flash Point: 236.2 °C
• PSA: 63.33000
• Density: 1.222 g/cm³
• LogP: 4.02580
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO
• Water Solubility.: 4mg/L(37 oC)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 293.10519334
• Heavy Atom Count: 22
• Complexity: 361

Purity/Quality:

99% ^*data from raw suppliers

Oxaprozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36/37/39-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: C1=CC=C(C=C1)C2=C(OC(=N2)CCC(=O)O)C3=CC=CC=C3
• Recent ClinicalTrials: Drug-drug Interaction Study of FYU-981 and Oxaprozin
• Description: Oxaprozin is a non-steroidal antiinflammatory agent indicated for use in various forms of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. A long T1/2 allows once/twice daily dosing. Structurally it is somewhat unique, being a 3- substituted, rather than a 2-substituted propionic acid.
• Uses: Oxaprozin is an anti-inflammatory drug. Oxaprozin was comparable to Aspirin (A687780). Anti-inflammatory antiparasitic
• Indications: Oxaprozin (Daypro) is approved for the treatment of osteoarthritis and rheumatoid arthritis. Its long halflife allows for once daily dosing.The most frequently reported adverse effects of this drug are nausea, vomiting, and dyspepsia.
• Therapeutic Function: Antiinflammatory

Technology Process of Oxaprozin

There total 18 articles about Oxaprozin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methyl 3-(4,5-diphenyloxazol-2-yl)propanoate (26820-94-0) → 3-(4,5-Diphenyl-oxazol-2-yl)-propionic acid (21256-18-8)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃;

DOI:10.1021/acs.joc.6b01280

Reference yield: 79.2%

phenyl benzyl ketone (451-40-1) → 3-(4,5-Diphenyl-oxazol-2-yl)-propionic acid (21256-18-8)

Guidance literature:

In nitromethane; at 60 - 80 ℃; for 1h;

Reference yield: 77.0%

3-(4,5-diphenyloxazol-2-yl)propanenitrile (123705-53-3) → 3-(4,5-Diphenyl-oxazol-2-yl)-propionic acid (21256-18-8)

Guidance literature:

3-(4,5-diphenyloxazol-2-yl)propanenitrile; With dihydrogen peroxide; sodium hydroxide; In 1,4-dioxane; water; at 100 ℃; for 20h; Inert atmosphere;

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1016/j.tet.2015.06.022

upstream raw materials:

phenyl benzyl ketone

succinic acid anhydride

2-hydroxy-2-phenylacetophenone

Benzoin-hemisuccinat

Downstream raw materials:

ethyl 5-(4,5-diphenyl-2-oxazolyl)pentan-3-onate

5-(4,5-diphenyl-2-oxazolyl)-3-aminopentanoic acid

ethyl 5-(4,5-diphenyl-2-oxazolyl)-3-aminopentanoate

ethyl 5-(4,5-diphenyl-2-oxazolyl)-3-amino-2-pentenoate

Refernces

• 1、 Patil, Pravin C.,Luzzio, Frederick A.. "Synthesis of Extended Oxazoles III: Reactions of 2-(Phenylsulfonyl)methyl-4,5-diaryloxazoles". . p. 10521 - 10526. Retrieved 2016/11/17.
• 2、 Kim, Yongjin,Pak, Han Kyu,Rhee, Young Ho,Park, Jaiwook. "Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones". supporting information. p. 6549 - 6552. Retrieved 2016/06/01.