2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid

• ChemBase ID: 4356
• Molecular Formular: C16H12ClNO3
• Molecular Mass: 301.72438
• Monoisotopic Mass: 301.05057093
• SMILES: Clc1ccc(c2oc3c(n2)cc(C(C)C(=O)O)cc3)cc1
• Canonical SMILES: OC(=O)C(c1ccc2c(c1)nc(o2)c1ccc(cc1)Cl)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
• IUPAC Traditional name: benoxaprofen
• Brand Name: Coxigon; Inflamid; Opren; Oraflex; Uniprofen
• 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; (1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acid; 2-(2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl)propanoic acid; 2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid; 2-[2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid; Benoxaprofene [inn-french]; Benoxaprofeno [inn-spanish]; Benoxaprofenum [inn-latin]; DL-benoxaprofen; Benoxaprofen

Database IDs

• CAS Number: 51234-28-7; 67434-14-4
• PubChem SID: 46508496; 160967788
• PubChem CID: 39941
• ATC CODE: M01AE06
• CHEMBL: 340978
• Chemspider ID: 36518
• DrugBank ID: DB04812
• Unique Ingredient Identifier: 17SZX404IM
• Wikipedia Title: Benoxaprofen

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.656784
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.2288494
• LogD (pH = 7.4): 1.451201
• Log P: 4.129415
• Molar Refractivity: 88.5116 cm^3
• Polarizability: 31.996813 Å^3
• Polar Surface Area: 63.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.22
• LOG S: -3.98
• Solubility (Water): 3.17e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.23 [JACK,DB ET AL. (1988)]

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB04812

• Drug Groups: withdrawn
• Description: The use of benoxaprofen, formerly marketed as Oraflex tablets, was associated with fatal cholestatic jaundice among other serious adverse reactions. The holder of the approved application voluntarily withdrew Oraflex tablets from the market on August 5, 1982.
• Affected Organisms: Humans and other mammals

Toronto Research Chemicals - B165300

A non-steroidal anti-inflammatory ophthalmic agent.

REFERENCES

• Mathur, K., et al.: Bioorg. Med. Chem., 11, 1915 (2003)
• Zhao, M., et al.: Bioorg. Med. Chem., 15, 2815 (2003)
• Roy, K., et al.: Eur. J. Med. Chem., 44, 2913 (2003)