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Benoxaprofen

Benoxaprofen structure

CAS No:
51234-28-7
Formula:
C16H12ClNO3
Chemical Name:
Benoxaprofen
Synonyms:
5-Benzoxazoleacetic acid,2-(4-chlorophenyl)-α-methyl-;2-(4-Chlorophenyl)-α-methyl-5-benzoxazoleacetic acid;Benoxaprofen;LRCL 3794;Lilly 90459;Oraflex;Opren;(±)-Benoxaprofen;(RS)-Benoxaprofen;dl-Benoxaprofen;(±)-2-(4-Chlorophenyl)-α-methyl-5-benzoxazoleacetic acid;Coxigon;Compound 90459;Uniprofen;NSC 299582;2-[2-(4-Chlorophenyl)benzoxazol-5-yl]-propanoic acid;299582Q1;2-(2-(4-Chlorophenyl)benzo[d]oxazol-5-yl)propanoic acid;67434-14-4
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

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 It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals.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, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antipyretic, a non-narcotic analgesic, a protein kinase C agonist, a hepatotoxic agent, an antipsoriatic and a nephrotoxin. It is a member of 1,3-benzoxazoles, a monocarboxylic acid and a member of monochlorobenzenes. It derives from a propionic acid.|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.

Benoxaprofen Basic Attributes

Molecular Weight：

301.72 g/mol

Exact Mass：

301.72

EC Number：

257-069-7

NSC Number：

299582

DSSTox ID：

DTXSID4022650

ATC Code：

M - Musculo-skeletal system

Characteristics

PSA：

63.3 Å²

XLogP3：

3.23 (LogP)

Melting Point：

189-190 °C

Safety Information

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P273, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

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. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)|Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)|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. (See all compounds classified as Lipoxygenase Inhibitors.)

MeSH Entry Terms：

benoxaprofen

Benoxaprofen Use and Manufacturing

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:301.72
XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:301.0505709
Monoisotopic Mass:301.0505709
Topological Polar Surface Area:63.3
Heavy Atom Count:21
Complexity:384
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes