For research use only. Not for therapeutic Use.
Benoxaprofen, also known as Benoxaphen, is a non-steroidal anti-inflammatory drug developed by Eli Lilly and Company. Lilly suspended sales of Oraflex in 1982 after reports from the British government and the U.S. Food and Drug Administration (FDA) of adverse effects and deaths linked to the drug.
| Catalog Number | R049354 |
| CAS Number | 51234-28-7 |
| Synonyms | 2-(4-Chlorophenyl)-α-methyl-5-benzoxazoleacetic Acid; (RS)-Benoxaprofen; (+/-)-Benoxaprofen; 2-[2-(4-Chlorophenyl)benzoxazol-5-yl]-propanoic Acid; Compound 90459; Coxigon; LRCL 3794; Lilly 90459; NSC 299582; Opren; Oraflex; Uniprofen; dl-Benoxaprof |
| Molecular Formula | C16H12ClNO3 |
| Purity | ≥95% |
| Target | COX |
| Storage | -20°C |
| IUPAC Name | 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid |
| InChI | InChI=1S/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20) |
| InChIKey | MITFXPHMIHQXPI-UHFFFAOYSA-N |
| SMILES | CC(C1=CC2=C(C=C1)OC(=N2)C3=CC=C(C=C3)Cl)C(=O)O |
| Reference | </br>1:Melanoma diagnosed 27 years after a benoxaprofen-induced photosensitivity reaction. Chin KY, El-Kayat B, Milne A, Hart A.J Dermatol Case Rep. 2012 Mar 27;6(1):5-7. doi: 10.3315/jdcr.2012.1087. PMID: 22514582 Free PMC Article</br>2:Effects of clofibric acid on the biliary excretion of benoxaprofen glucuronide and taurine conjugate in rats. Okada K, Kanoh H, Mohri K.Pharmazie. 2011 Oct;66(10):777-83. PMID: 22026160 </br>3:Glucuronidation and covalent protein binding of benoxaprofen and flunoxaprofen in sandwich-cultured rat and human hepatocytes. Dong JQ, Smith PC.Drug Metab Dispos. 2009 Dec;37(12):2314-22. doi: 10.1124/dmd.109.028944. Epub 2009 Sep 22. PMID: 19773537 Free PMC Article</br>4:Role of benoxaprofen and flunoxaprofen acyl glucuronides in covalent binding to rat plasma and liver proteins in vivo. Dong JQ, Liu J, Smith PC.Biochem Pharmacol. 2005 Sep 15;70(6):937-48. PMID: 16046212 </br>5:Stereoselective taurine conjugation of (R)-benoxaprofen enantiomer in rats: in vivo and in vitro studies using rat hepatic mitochondria and microsomes. Mohri K, Okada K, Benet LZ.Pharm Res. 2005 Jan;22(1):79-85. PMID: 15771233 </br>6:Effect of selective phase II enzyme inducers on glucuronidation of benoxaprofen in rats. Dong JQ, Etheridge AS, Smith PC.Drug Metab Dispos. 1999 Dec;27(12):1423-8. PMID: 10570023 Free Article</br>7:Stereoselective metabolism of benoxaprofen in rats. Biliary excretion of benoxaprofen taurine conjugate and glucuronide. Mohri K, Okada K, Benet LZ.Drug Metab Dispos. 1998 Apr;26(4):332-7. PMID: 9531520 Free Article</br>8:Mechanisms for covalent binding of benoxaprofen glucuronide to human serum albumin. Studies By tandem mass spectrometry. Qiu Y, Burlingame AL, Benet LZ.Drug Metab Dispos. 1998 Mar;26(3):246-56. PMID: 9492388 Free Article</br>9:Covalent binding of acidic drugs via reactive intermediates: detection of benoxaprofen and flunoxaprofen protein adducts in biological material. Dahms M, Spahn-Langguth H.Pharmazie. 1996 Nov;51(11):874-81. PMID: 8985978 </br>10:Comparison of the pro-oxidative interactions of flunoxaprofen and benoxaprofen with human polymorphonuclear leucocytes in vitro. Van Rensburg AJ, Theron AJ, Anderson R.Agents Actions. 1991 Jul;33(3-4):292-9. PMID: 1950816 |
