Basic information
- CAS
51234-28-7- Standard SMILES
CC(C(=O)O)c1ccc2oc(-c3ccc(Cl)cc3)nc2c1- InChIKey
MITFXPHMIHQXPI-UHFFFAOYSA-N- Molecular formula
- C16H12ClNO3
- Average molar mass
- 301.72 g/mol
- Monoisotopic mass
- 301.0505709
Overview
Benoxaprofen is a monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group. It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an antipsoriatic, a hepatotoxic agent, a nephrotoxic agent, a protein kinase C agonist and an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor. It is a monocarboxylic acid, a member of 1,3-benzoxazoles and a member of monochlorobenzenes. It is functionally related to a propionic acid.
Names & identifiers
- Preferred name
- Benoxaprofen
- IUPAC
- 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
- English name
- Uniprofen
- Molecular formula
- C16H12ClNO3
- Molecular weight
- 301.73
Names & synonyms
Benoxaprofen51234-28-7OraflexCoxigonOprendl-BenoxaprofenBenoxaprofeneCompound 90459BenoxaprofenumBenoxaprofeno2-[2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acidLilly 90459
Show more names
InflamidLY-90459UniprofenLRCL-3794NSC 299582Aids128826Lilly-90459
(+-)-benoxaprofen2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acidCOMPOUND-90459(1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acidCOMPD 90459NSC-29958217SZX404IMCHEBI:76114
Database identifiers
- CAS
51234-28-7、67434-14-4- PubChem CID
- 39941
- DTXSID
DTXSID4022650- ChEMBL
CHEMBL340978- ChEBI
CHEBI:76114- UNII
- 17SZX404IM
- EC Number
- 257-069-7、266-692-3
- Nikkaji
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 384
Experimental & physicochemical properties
Human DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 189.5 °C · 189.5°C
- Boiling point
- 446.2 · 446.2±30.0 °C(Predicted)
- Density
- 1.2411 · 1.2411 (rough estimate)
- refractive index
- 1.647 · 1.6470 (estimate)
- storage temp.
- Refrigerator
- solubility
- DMSO: slightly; Methanol: slightly, sonicated
- form
- A solid
- pka
- 4.36 · 4.36±0.30(Predicted)
- color
- Cream solid from EtOH
- FDA UNII
- 17 SZX404IM · 17SZX404IM
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302;H315;H319;H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Benoxaprofen
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Safety data
- Toxicity
- LD50 oral in rat: 118mg/kg
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302;H315;H319;H335
- Precautionary statements
- P261;P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Drugs used to treat or prevent skin disorders or for the routine care of skin.
Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES.
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesA non-steroidal anti-inflammatory ophthalmic agent.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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