mefenamic acid Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory, anthranilic acid derivatives 1663 61-68-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mefenamic acid
  • mefenacid
  • mephenamic acid
  • mefenamate
A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.
  • Molecular weight: 241.29
  • Formula: C15H15NO2
  • CLOGP: 5.14
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 2
  • TPSA: 49.33
  • ALOGS: -4.25
  • ROTB: 3

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.08 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 74.01 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 28, 1967 FDA SHIONOGI INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Tubulointerstitial nephritis 85.39 44.26 16 191 2422 2355456
Drug reaction with eosinophilia and systemic symptoms 77.95 44.26 17 190 5501 2352377
Acute kidney injury 75.53 44.26 23 184 28099 2329779
Urinoma 62.67 44.26 7 200 21 2357857
Synovitis 59.14 44.26 12 195 2714 2355164
Swelling 55.10 44.26 16 191 16334 2341544
Dactylitis 53.55 44.26 7 200 96 2357782
Vomiting 51.14 44.26 22 185 71580 2286298
Urine osmolarity increased 50.49 44.26 6 201 35 2357843
Enthesopathy 50.17 44.26 7 200 160 2357718
Nephrogenic diabetes insipidus 49.16 44.26 7 200 186 2357692
Menopausal symptoms 44.47 44.26 7 200 370 2357508

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Heat stroke 63.56 50.01 9 121 225 1746426
Acute kidney injury 62.38 50.01 21 109 34923 1711728

Pharmacologic Action:

SourceCodeDescription
ATC M01AG01 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Fenamates
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35842 antirheumatic drug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35493 antipyretic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Dysmenorrhea indication 266599000
Vascular headache off-label use 128187005
Peptic ulcer contraindication 13200003 DOID:750
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Blood coagulation disorder contraindication 64779008 DOID:1247
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.43 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 6.83 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 4.78 WOMBAT-PK CHEMBL
Aldo-keto reductase family 1 member C1 Enzyme Ki 6.09 CHEMBL
Cytochrome P450 2C9 Enzyme EC50 5.30 WOMBAT-PK
Aldo-keto reductase family 1 member B10 Enzyme IC50 5.80 CHEMBL
Aldo-keto reductase family 1 member C3 Enzyme Ki 6.52 CHEMBL
Aldose reductase Enzyme IC50 4.11 CHEMBL
Aldo-keto reductase family 1 member C2 Enzyme Ki 6.66 CHEMBL
Acetylcholinesterase Enzyme IC50 5.21 CHEMBL

External reference:

IDSource
4019082 VUID
N0000147343 NUI
C0025152 UMLSCUI
D00151 KEGG_DRUG
367589PJ2C UNII
1494 INN_ID
34364009 SNOMEDCT_US
4019082 VANDF
6693 RXNORM
387185008 SNOMEDCT_US
5034 MMSL
d00285 MMSL
91405 MMSL
001578 NDDF
4044 PUBCHEM_CID
CHEBI:6717 CHEBI
CHEMBL686 ChEMBL_ID
DB00784 DRUGBANK_ID
ID8 PDB_CHEM_ID
D008528 MESH_DESCRIPTOR_UI
2593 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mefenamic acid HUMAN PRESCRIPTION DRUG LABEL 1 42571-258 CAPSULE 250 mg ORAL ANDA 13 sections
Mefenamic Acid HUMAN PRESCRIPTION DRUG LABEL 1 51991-839 CAPSULE 250 mg ORAL ANDA 14 sections
Mefenamic Acid HUMAN PRESCRIPTION DRUG LABEL 1 62250-677 CAPSULE 250 mg ORAL ANDA 15 sections
Mefenamic Acid HUMAN PRESCRIPTION DRUG LABEL 1 68180-185 CAPSULE 250 mg ORAL ANDA 13 sections