CHEBI:76114 - benoxaprofen

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ChEBI Name benoxaprofen
ChEBI ID CHEBI:76114
Definition 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 It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H12ClNO3
Net Charge 0
Average Mass 301.72400
Monoisotopic Mass 301.05057
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(C(O)=O)c1ccc2oc(nc2c1)-c1ccc(Cl)cc1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): hepatotoxic agent
A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor
A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34).
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
protein kinase C agonist
An agonist that selectively binds to and activates a protein kinase C receptor
nephrotoxin
A poison that interferes with the function of the kidneys.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs 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.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antipsoriatic
A drug used to treat psoriasis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing benoxaprofen (CHEBI:76114) has functional parent propionic acid (CHEBI:30768)
benoxaprofen (CHEBI:76114) has role antipsoriatic (CHEBI:50748)
benoxaprofen (CHEBI:76114) has role antipyretic (CHEBI:35493)
benoxaprofen (CHEBI:76114) has role EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor (CHEBI:64964)
benoxaprofen (CHEBI:76114) has role hepatotoxic agent (CHEBI:50908)
benoxaprofen (CHEBI:76114) has role nephrotoxin (CHEBI:61015)
benoxaprofen (CHEBI:76114) has role non-narcotic analgesic (CHEBI:35481)
benoxaprofen (CHEBI:76114) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
benoxaprofen (CHEBI:76114) has role protein kinase C agonist (CHEBI:64018)
benoxaprofen (CHEBI:76114) is a 1,3-benzoxazoles (CHEBI:51548)
benoxaprofen (CHEBI:76114) is a monocarboxylic acid (CHEBI:25384)
benoxaprofen (CHEBI:76114) is a monochlorobenzenes (CHEBI:83403)
IUPAC Name
2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
INNs Sources
benoxaprofen KEGG DRUG
benoxaprofene DrugBank
benoxaprofeno DrugBank
benoxaprofenum DrugBank
Synonyms Sources
(±)-benoxaprofen ChemIDplus
(1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acid ChemIDplus
2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid ChemIDplus
2-(4-chlorophenyl)-α-methyl-5-benzoxazoleacetic acid NIST Chemistry WebBook
2-(p-chlorophenyl)-α-methyl-5-benzoxazoleacetic acid NIST Chemistry WebBook
DL-benoxaprofen DrugBank
Lilly 90459 ChemIDplus
Manual Xrefs Databases
311 DrugCentral
Benoxaprofen Wikipedia
D03080 KEGG DRUG
DB04812 DrugBank
DE2324443 Patent
US3912748 Patent
US4391814 Patent
US6338855 Patent
WO2008020270 Patent
View more database links
Registry Numbers Types Sources
1085080 Reaxys Registry Number Reaxys
51234-28-7 CAS Registry Number NIST Chemistry WebBook
51234-28-7 CAS Registry Number KEGG DRUG
51234-28-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017