CHEBI:75915 - amfenac

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ChEBI Name amfenac
ChEBI ID CHEBI:75915
Definition An oxo monocarboxylic acid that is benzophenone in which one of the phenyl groups is substituted by an amino group and a carboxymethyl group at position 2 and 3, respectively. The corresponding carboxamide, nepafenac, is a prodrug of amfenac and is used for the treatment of pain and inflammation following cataract surgery.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H13NO3
Net Charge 0
Average Mass 255.26860
Monoisotopic Mass 255.090
InChI InChI=1S/C15H13NO3/c16-14-11(9-13(17)18)7-4-8-12(14)15(19)10-5-2-1-3-6-10/h1-8H,9,16H2,(H,17,18)
InChIKey SOYCMDCMZDHQFP-UHFFFAOYSA-N
SMILES Nc1c(CC(O)=O)cccc1C(=O)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): cyclooxygenase 2 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Application(s): 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.
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.
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ChEBI Ontology
Outgoing amfenac (CHEBI:75915) has role antipyretic (CHEBI:35493)
amfenac (CHEBI:75915) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
amfenac (CHEBI:75915) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
amfenac (CHEBI:75915) has role non-narcotic analgesic (CHEBI:35481)
amfenac (CHEBI:75915) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
amfenac (CHEBI:75915) is a amino acid (CHEBI:33709)
amfenac (CHEBI:75915) is a benzophenones (CHEBI:22726)
amfenac (CHEBI:75915) is a oxo monocarboxylic acid (CHEBI:35871)
amfenac (CHEBI:75915) is a primary amino compound (CHEBI:50994)
amfenac (CHEBI:75915) is a substituted aniline (CHEBI:48975)
amfenac (CHEBI:75915) is conjugate acid of amfenac(1−) (CHEBI:75917)
Incoming bromfenac (CHEBI:240107) has functional parent amfenac (CHEBI:75915)
amfenac(1−) (CHEBI:75917) is conjugate base of amfenac (CHEBI:75915)
IUPAC Name
(2-amino-3-benzoylphenyl)acetic acid
INNs Sources
amfenac ChemIDplus
amfénac WHO MedNet
amfenaco ChemIDplus
amfenacum ChemIDplus
Synonyms Sources
(2-Amino-3-benzoylphenyl)essigsaeure ChemIDplus
2-amino-3-benzoylbenzeneacetic acid ChEBI
Manual Xrefs Databases
154 DrugCentral
Amfenac Wikipedia
D07443 KEGG DRUG
DE2324768 Patent
US4045576 Patent
View more database links
Registry Numbers Types Sources
2381781 Reaxys Registry Number Reaxys
51579-82-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10850857 PubMed citation Europe PMC
19897019 PubMed citation Europe PMC
3540874 PubMed citation Europe PMC
8320556 PubMed citation Europe PMC
Last Modified
22 February 2017