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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:36 UTC
HMDB IDHMDB0014922
Secondary Accession Numbers
  • HMDB14922
Metabolite Identification
Common NameMefenamic acid
DescriptionMefenamic acid, also known as ponstel or acide mefenamique, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Mefenamic acid undergoes metabolism by CYP2C9 to 3-hydroxymethyl mefenamic acid, and further oxidation to a 3-carboxymefenamic acid may occur. Mefenamic acid, an anthranilic acid derivative, is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). The activity of these metabolites has not been studied. Mefenamic acid is a drug which is used for the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever. Mefenamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, mefenamic acid is involved in mefenamic acid action pathway. Mefenamic acid binds the prostaglandin synthetase receptors COX-1 and COX-2, inhibiting the action of prostaglandin synthetase. It is an inhibitor of cyclooxygenase. Mefenamic acid is only found in individuals that have used or taken this drug.
Structure
Data?1582753236
Synonyms
ValueSource
Acide mefenamiqueChEBI
Acido mefenamicoChEBI
Acidum mefenamicumChEBI
CI-473ChEBI
CN 35355ChEBI
CN-35355ChEBI
INF 3355ChEBI
INF-3355ChEBI
MefenaminsaeureChEBI
N-(2,3-Xylyl)-2-aminobenzoic acidChEBI
N-2,3-Xylylanthranilic acidChEBI
PonstelChEBI
N-(2,3-Xylyl)-2-aminobenzoateGenerator
N-2,3-XylylanthranilateGenerator
MefenamateGenerator
Mefanamic acidHMDB
MefenacidHMDB
Mephenamic acidHMDB
Mephenaminic acidHMDB
Methenamic acidHMDB
Acid, mefenaminicHMDB
Antigen brand OF mefenamic acidHMDB
Apo-mefenamicHMDB
Ashbourne brand OF mefenamic acidHMDB
CoslanHMDB
Forte, ponstanHMDB
MefacitHMDB
MeficHMDB
Nu-mefenamicHMDB
PMS-Mefenamic acidHMDB
Pfizer brand OF mefenamic acidHMDB
Pinewood brand OF mefenamic acidHMDB
PonalarHMDB
APS brand OF mefenamic acidHMDB
Apo mefenamicHMDB
Apotex brand OF mefenamic acidHMDB
DysmanHMDB
First horizon brand OF mefenamic acidHMDB
Gödecke brand OF mefenamic acidHMDB
Mefenaminic acidHMDB
NuMefenamicHMDB
PMS Mefenamic acidHMDB
PonalgicHMDB
Warner-lambert brand OF mefenamic acidHMDB
Chemidex brand OF mefenamic acidHMDB
ContraflamHMDB
Elan brand OF mefenamic acidHMDB
Farmasierra brand OF mefenamic acidHMDB
Nu-pharm brand OF mefenamic acidHMDB
Parke davis brand OF mefenamic acidHMDB
ParkemedHMDB
PinalgesicHMDB
PonmelHMDB
PontalHMDB
Rowa brand OF mefenamic acidHMDB
Acid, mefenamicHMDB
ApoMefenamicHMDB
Clonmel brand OF mefenamic acidHMDB
MefacHMDB
Nu mefenamicHMDB
Nu pharm brand OF mefenamic acidHMDB
Pharmascience brand OF mefenamic acidHMDB
PonstanHMDB
Ponstan forteHMDB
PonsylHMDB
Warner lambert brand OF mefenamic acidHMDB
Chemical FormulaC15H15NO2
Average Molecular Weight241.2851
Monoisotopic Molecular Weight241.110278729
IUPAC Name2-[(2,3-dimethylphenyl)amino]benzoic acid
Traditional Namemefenamic acid
CAS Registry Number61-68-7
SMILES
CC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C1
InChI Identifier
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)
InChI KeyHYYBABOKPJLUIN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Xylene
  • O-xylene
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point230 - 231 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.58ALOGPS
logP5.4ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.88 m³·mol⁻¹ChemAxon
Polarizability26.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fv-0970000000-ac788fb2c3de77e0c447Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fdn-1190000000-766d0be9c0eb20d0bbe3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-02t9-0900000000-97aeacf66e8410c23139Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-e81bfb47482e34427f9dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0090000000-c35efe26003cb812152aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0005-0960000000-902cd19e4e1d6d83389bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-36a2c798555c3d7096f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-0aaa97d98cb6e792e5daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0005-0900000000-8550ea073cfe0222a6ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-2900000000-fc439b80f6648ed94d76Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0090000000-be477416d623ed244bdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0005-0960000000-414fb8a03460842ef79aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-0acd19e33bc790381da7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-c2637ad61718ba056356Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0005-0900000000-cf0ec9e01efae551956cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-1900000000-e53da7b0c2cd925ff45fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-6d3e988a836ba090f290Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0090000000-9e70a08d5d730c15aa69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-0950000000-a6ebc54abcd1d821d31eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-58bf82bda5da2fed93ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0005-0900000000-f699cc613c8f7da1d256Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0390000000-126e782feabd9bc49b1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0595-0950000000-3c37ad79df77f9854764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4910000000-e4322857bc9bd2c48dddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-0970000000-a26d55ca757d99074377Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0910000000-f3ff4dc6f1dc1c7a0573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000y-4900000000-26ffaf3603b933b04606Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00784 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00784 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00784
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3904
KEGG Compound IDC02168
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMefenamic_acid
METLIN IDNot Available
PubChem Compound4044
PDB IDID8
ChEBI ID6717
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Gierse JK, Hauser SD, Creely DP, Koboldt C, Rangwala SH, Isakson PC, Seibert K: Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem J. 1995 Jan 15;305 ( Pt 2):479-84. [PubMed:7832763 ]
  2. Bhat AS, Tandan SK, Kumar D, Krishna V, Prakash VR: Interaction between inhibitors of inducible nitric oxide synthase and cyclooxygenase in adjuvant-induced arthritis in female albino rats: an isobolographic study. Eur J Pharmacol. 2007 Feb 5;556(1-3):190-9. Epub 2006 Oct 27. [PubMed:17150210 ]
  3. Bhat AS, Tandan SK, Kumar D, Krishna V, Prakash VR: Interaction between inhibitors of inducible nitric oxide synthase and cyclooxygenase in Brewer's yeast induced pyrexia in mice: an isobolographic study. Eur J Pharmacol. 2005 Mar 28;511(2-3):137-42. [PubMed:15792781 ]
  4. Cryer B, Feldman M: Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs. Am J Med. 1998 May;104(5):413-21. [PubMed:9626023 ]
  5. Walton LJ, Franklin IJ, Bayston T, Brown LC, Greenhalgh RM, Taylor GW, Powell JT: Inhibition of prostaglandin E2 synthesis in abdominal aortic aneurysms: implications for smooth muscle cell viability, inflammatory processes, and the expansion of abdominal aortic aneurysms. Circulation. 1999 Jul 6;100(1):48-54. [PubMed:10393680 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Sinniah R, Lye WC: Acute renal failure from hemoglobinuric and interstitial nephritis secondary to iodine and mefenamic acid. Clin Nephrol. 2001 Mar;55(3):254-8. [PubMed:11316248 ]
  2. Joo Y, Kim HS, Woo RS, Park CH, Shin KY, Lee JP, Chang KA, Kim S, Suh YH: Mefenamic acid shows neuroprotective effects and improves cognitive impairment in in vitro and in vivo Alzheimer's disease models. Mol Pharmacol. 2006 Jan;69(1):76-84. Epub 2005 Oct 13. [PubMed:16223958 ]
  3. Cryer B, Feldman M: Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs. Am J Med. 1998 May;104(5):413-21. [PubMed:9626023 ]
  4. Gierse JK, Hauser SD, Creely DP, Koboldt C, Rangwala SH, Isakson PC, Seibert K: Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem J. 1995 Jan 15;305 ( Pt 2):479-84. [PubMed:7832763 ]
  5. Laudanno OM, Cesolari JA, Esnarriaga J, Flaherty P, Vada J, Guastalli G, San Miguel P, Bedini OA: [In vivo selectivity of nonsteroidal anti-inflammatory drugs on COX-1-COX-2 and gastrointestinal ulcers, in rats]. Acta Gastroenterol Latinoam. 1998;28(3):249-55. [PubMed:9773153 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]