CHEBI:6717 - mefenamic acid

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ChEBI Name mefenamic acid
ChEBI ID CHEBI:6717
Definition An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H15NO2
Net Charge 0
Average Mass 241.28510
Monoisotopic Mass 241.110
InChI InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)
InChIKey HYYBABOKPJLUIN-UHFFFAOYSA-N
SMILES Cc1cccc(Nc2ccccc2C(O)=O)c1C
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
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.
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ChEBI Ontology
Outgoing mefenamic acid (CHEBI:6717) has role analgesic (CHEBI:35480)
mefenamic acid (CHEBI:6717) has role antipyretic (CHEBI:35493)
mefenamic acid (CHEBI:6717) has role antirheumatic drug (CHEBI:35842)
mefenamic acid (CHEBI:6717) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
mefenamic acid (CHEBI:6717) has role environmental contaminant (CHEBI:78298)
mefenamic acid (CHEBI:6717) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
mefenamic acid (CHEBI:6717) has role xenobiotic (CHEBI:35703)
mefenamic acid (CHEBI:6717) is a aminobenzoic acid (CHEBI:22495)
mefenamic acid (CHEBI:6717) is a secondary amino compound (CHEBI:50995)
IUPAC Name
2-[(2,3-dimethylphenyl)amino]benzoic acid
INNs Sources
acide méfénamique WHO MedNet
ácido mefenámico WHO MedNet
acidum mefenamicum ChemIDplus
mefenamic acid ChemIDplus
Synonyms Sources
CI-473 ChemIDplus
CN 35355 ChemIDplus
CN-35355 ChemIDplus
INF 3355 ChemIDplus
INF-3355 ChemIDplus
Mefenaminsaeure ChemIDplus
N-(2,3-xylyl)-2-aminobenzoic acid ChemIDplus
N-2,3-xylylanthranilic acid ChemIDplus
Brand Name Source
Ponstel KEGG DRUG
Manual Xrefs Databases
1663 DrugCentral
BE605302 Patent
C02168 KEGG COMPOUND
D00151 KEGG DRUG
DB00784 DrugBank
HMDB0014922 HMDB
ID8 PDBeChem
LSM-4085 LINCS
Mefenamic_acid Wikipedia
US3138636 Patent
View more database links
Registry Numbers Types Sources
2216243 Reaxys Registry Number Reaxys
61-68-7 CAS Registry Number KEGG COMPOUND
61-68-7 CAS Registry Number ChemIDplus
61-68-7 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
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6155061 PubMed citation Europe PMC
Last Modified
19 June 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag