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
Infusion site coldness 110.60 18.32 20 6612 186 46679244
Gamma-glutamyltransferase decreased 103.71 18.32 20 6612 271 46679159
Infusion site induration 83.50 18.32 20 6612 782 46678648
Mean cell haemoglobin decreased 78.00 18.32 25 6607 2887 46676543
Post-traumatic neck syndrome 72.72 18.32 20 6612 1361 46678069
Infusion site haemorrhage 63.75 18.32 20 6612 2154 46677276
Vasodilatation 61.93 18.32 20 6612 2365 46677065
Spinal pain 60.25 18.32 29 6603 9863 46669567
Inflammatory marker increased 52.34 18.32 22 6610 5453 46673977
Vein disorder 52.24 18.32 20 6612 3893 46675537
Retinal detachment 47.11 18.32 20 6612 5080 46674350
Peripheral coldness 45.64 18.32 24 6608 9831 46669599
Incontinence 42.80 18.32 23 6609 9839 46669591
Urinoma 41.13 18.32 7 6625 44 46679386
Poor venous access 37.81 18.32 20 6612 8288 46671142
Feeling cold 35.92 18.32 26 6606 18745 46660685
Blood creatinine decreased 35.50 18.32 16 6616 4688 46674742
Irritable bowel syndrome 34.19 18.32 24 6608 16491 46662939
Enthesopathy 32.39 18.32 15 6617 4675 46674755
Immunodeficiency 31.77 18.32 21 6611 13085 46666345
Body temperature decreased 31.34 18.32 21 6611 13388 46666042
Dactylitis 30.95 18.32 10 6622 1183 46678247
Skin sensitisation 30.32 18.32 9 6623 804 46678626
Urticaria 29.69 18.32 57 6575 117835 46561595
Toothache 29.53 18.32 22 6610 16570 46662860
Urine osmolarity increased 29.10 18.32 6 6626 116 46679314
Musculoskeletal disorder 26.30 18.32 20 6612 15525 46663905
Peripheral swelling 25.62 18.32 64 6568 158007 46521423
Tendon disorder 25.53 18.32 13 6619 4982 46674448
Blood potassium increased 24.75 18.32 20 6612 16947 46662483
Metastases to bone 24.24 18.32 20 6612 17456 46661974
Death 23.78 18.32 9 6623 335539 46343891
Chills 23.63 18.32 46 6586 95986 46583444
Arteriospasm coronary 23.21 18.32 11 6621 3610 46675820
Angioedema 22.75 18.32 28 6604 39314 46640116
Road traffic accident 22.70 18.32 22 6610 23669 46655761
Stress 22.56 18.32 32 6600 51519 46627911
Nephrogenic diabetes insipidus 22.29 18.32 7 6625 756 46678674
Cerebellar haemangioma 21.95 18.32 4 6628 39 46679391
Injection site bruising 21.64 18.32 26 6606 35610 46643820
Gastrointestinal inflammation 21.42 18.32 11 6621 4290 46675140
Mononeuropathy multiplex 21.01 18.32 5 6627 190 46679240
Abdominal pain upper 20.63 18.32 56 6576 145249 46534181
Haemangioma 20.35 18.32 9 6623 2520 46676910
Pain in jaw 20.10 18.32 26 6606 38346 46641084
Tension headache 19.87 18.32 9 6623 2665 46676765
Hepatic function abnormal 19.10 18.32 24 6608 34397 46645033
Sensory loss 19.05 18.32 12 6620 6890 46672540
Impaired driving ability 18.74 18.32 10 6622 4214 46675216
Tubulointerstitial nephritis 18.60 18.32 16 6616 14772 46664658
Rabbit syndrome 18.50 18.32 5 6627 318 46679112
Photosensitivity reaction 18.49 18.32 15 6617 12777 46666653
Flushing 18.45 18.32 33 6599 64581 46614849
Injection site mass 18.37 18.32 16 6616 15024 46664406
Musculoskeletal stiffness 18.36 18.32 42 6590 97951 46581479

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 68.94 27.40 14 1285 856 29950323
Ankylosing spondylitis 50.30 27.40 15 1284 4519 29946660
Anhidrosis 37.18 27.40 6 1293 98 29951081
Exposure to communicable disease 35.61 27.40 6 1293 129 29951050
Mydriasis 30.24 27.40 11 1288 6132 29945047

Pharmacologic Action:

SourceCodeDescription
ATC M01AG01 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Fenamates
FDA CS M0001335 Anti-Inflammatory Agents, Non-Steroidal
FDA MoA N0000000160 Cyclooxygenase Inhibitors
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
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
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drugs
CHEBI has role CHEBI:35493 anti-pyretic
CHEBI has role CHEBI:35544 cyclooxygenase inhibitors
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:35842 antirheumatic agent
CHEBI has role CHEBI:78298 environmental contaminants

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
D00151 KEGG_DRUG
4019082 VANDF
C0806919 UMLSCUI
CHEBI:6717 CHEBI
ID8 PDB_CHEM_ID
CHEMBL686 ChEMBL_ID
D008528 MESH_DESCRIPTOR_UI
DB00784 DRUGBANK_ID
2593 IUPHAR_LIGAND_ID
1494 INN_ID
367589PJ2C UNII
4044 PUBCHEM_CID
257844 RXNORM
5034 MMSL
91405 MMSL
d00285 MMSL
001578 NDDF
116727007 SNOMEDCT_US
34364009 SNOMEDCT_US
387185008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Mefenamic acid HUMAN PRESCRIPTION DRUG LABEL 1 42571-258 CAPSULE 250 mg ORAL ANDA 24 sections
Mefenamic Acid HUMAN PRESCRIPTION DRUG LABEL 1 62250-677 CAPSULE 250 mg ORAL ANDA 27 sections
Mefenamic Acid HUMAN PRESCRIPTION DRUG LABEL 1 64380-790 CAPSULE 250 mg ORAL ANDA 25 sections
Mefenamic Acid HUMAN PRESCRIPTION DRUG LABEL 1 68180-185 CAPSULE 250 mg ORAL ANDA 23 sections