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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014922
Secondary Accession Numbers
  • HMDB14922
Metabolite Identification
Common NameMefenamic acid
DescriptionMefenamic acid is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase. [PubChem]Mefenamic acid binds the prostaglandin synthetase receptors COX-1 and COX-2, inhibiting the action of prostaglandin synthetase. As these receptors have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity, the symptoms of pain are temporarily reduced.
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point230 - 231 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 g/LNot Available
LogP4.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available153.308http://allccs.zhulab.cn/database/detail?ID=AllCCS00000769
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.31331661259
DarkChem[M-H]-153.94131661259
DeepCCS[M+H]+153.48530932474
DeepCCS[M-H]-151.12730932474
DeepCCS[M-2H]-184.12230932474
DeepCCS[M+Na]+159.57830932474
AllCCS[M+H]+153.732859911
AllCCS[M+H-H2O]+149.732859911
AllCCS[M+NH4]+157.332859911
AllCCS[M+Na]+158.432859911
AllCCS[M-H]-157.332859911
AllCCS[M+Na-2H]-156.832859911
AllCCS[M+HCOO]-156.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Mefenamic acidCC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C13376.3Standard polar33892256
Mefenamic acidCC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C12219.3Standard non polar33892256
Mefenamic acidCC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C12183.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mefenamic acid,1TMS,isomer #1CC1=CC=CC(NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=C1C2194.9Semi standard non polar33892256
Mefenamic acid,1TMS,isomer #2CC1=CC=CC(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=C1C2126.8Semi standard non polar33892256
Mefenamic acid,2TMS,isomer #1CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1C2127.8Semi standard non polar33892256
Mefenamic acid,2TMS,isomer #1CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1C2233.1Standard non polar33892256
Mefenamic acid,2TMS,isomer #1CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1C2474.1Standard polar33892256
Mefenamic acid,1TBDMS,isomer #1CC1=CC=CC(NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=C1C2448.6Semi standard non polar33892256
Mefenamic acid,1TBDMS,isomer #2CC1=CC=CC(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=C1C2383.0Semi standard non polar33892256
Mefenamic acid,2TBDMS,isomer #1CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C2607.3Semi standard non polar33892256
Mefenamic acid,2TBDMS,isomer #1CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C2586.6Standard non polar33892256
Mefenamic acid,2TBDMS,isomer #1CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C2736.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mefenamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fv-0970000000-ac788fb2c3de77e0c4472017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mefenamic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fdn-1190000000-766d0be9c0eb20d0bbe32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mefenamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-qTof , Positive-QTOFsplash10-02t9-0900000000-97aeacf66e8410c231392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-e81bfb47482e34427f9d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0006-0090000000-c35efe26003cb812152a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0005-0960000000-902cd19e4e1d6d83389b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-36a2c798555c3d7096f22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-0aaa97d98cb6e792e5da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0005-0900000000-8550ea073cfe0222a6cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0006-2900000000-fc439b80f6648ed94d762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0006-0090000000-be477416d623ed244bdb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0005-0960000000-414fb8a03460842ef79a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-0acd19e33bc790381da72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-c2637ad61718ba0563562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0005-0900000000-cf0ec9e01efae551956c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0006-1900000000-e53da7b0c2cd925ff45f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-ITFT , negative-QTOFsplash10-0002-0900000000-6d3e988a836ba090f2902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-QQ , negative-QTOFsplash10-0006-0090000000-9e70a08d5d730c15aa692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-QQ , negative-QTOFsplash10-0005-0950000000-a6ebc54abcd1d821d31e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-QQ , negative-QTOFsplash10-0002-0900000000-58bf82bda5da2fed93cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mefenamic acid LC-ESI-QQ , negative-QTOFsplash10-0005-0900000000-f699cc613c8f7da1d2562017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mefenamic acid 10V, Positive-QTOFsplash10-0006-0390000000-126e782feabd9bc49b1c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mefenamic acid 20V, Positive-QTOFsplash10-0595-0950000000-3c37ad79df77f98547642016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mefenamic acid 40V, Positive-QTOFsplash10-0a4i-4910000000-e4322857bc9bd2c48ddd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mefenamic acid 10V, Negative-QTOFsplash10-0005-0970000000-a26d55ca757d990743772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mefenamic acid 20V, Negative-QTOFsplash10-0002-0910000000-f3ff4dc6f1dc1c7a05732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mefenamic acid 40V, Negative-QTOFsplash10-000y-4900000000-26ffaf3603b933b046062016-08-03Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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 ]