MEFENAMIC ACID

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC M01AG01
UNII 367589PJ2C
EPA CompTox DTXSID5023243

Structure

InChI Key HYYBABOKPJLUIN-UHFFFAOYSA-N
Smiles Cc1cccc(Nc2ccccc2C(=O)O)c1C
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H15NO2
Molecular Weight 241.29
AlogP 3.75
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 49.33
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 18.0

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase inhibitor INHIBITOR PubMed PubMed
Protein: Cyclooxygenase
Description: Prostaglandin G/H synthase 1
Organism : Homo sapiens
P23219 ENSG00000095303
Protein: Cyclooxygenase
Description: Prostaglandin G/H synthase 2
Organism : Homo sapiens
P35354 ENSG00000073756
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 6120 - - -
Enzyme Oxidoreductase
- 980-2210 - 220 -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- - - - 39
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- - - - 36
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- - - - 41
Enzyme
- 980-2210 - 220 36
Ion channel Voltage-gated ion channel Transient receptor potential channel
16000-61000 - - - -
Secreted protein
- - - - 93
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 63
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 57000 - - -
Unclassified protein
- 25000 - - -
Assay Description Organism Bioactivity Reference
Fold decrease in IC50 vs beta-lactamase on pre-incubation Escherichia coli 3.0
Fold increase in IC50 vs chymotrypsinogen with 0.1 mg/ml saponin None 2.0
Fold decrease in IC50 vs chymotrypsinogen on pre-incubation None 2.0
Compound was tested for the inhibition of Chymotrypsinogen at 400 uM None 41.0 %
Compound is evaluated for the inhibition of [125I]T3 uptake by H4 rat hepatoma cells at 0.1 mM Rattus norvegicus 60.9 %
Fold decrease in IC50 vs malate dehydrogenase (MDH) on pre-incubation None 3.0
Compound was tested for antiinflammatory activity and the % inhibition was reported 3 h after carrageenan injection in the hind paw edema test in rats: dose=40 mg/kg, p.o. Rattus norvegicus 33.1 %
Fold increase in IC50 vs beta-lactamaase with 1 mg/mL saponin Escherichia coli 3.0
Fold increase in IC50 vs beta-lactamase with 10x increased enzyme None 50.0
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, po administered 30 mins before carrageenan challenge measured after 0.5 hrs Rattus norvegicus 16.7 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, po administered 30 mins before carrageenan challenge measured after 1 hr Rattus norvegicus 18.3 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, po administered 30 mins before carrageenan challenge measured after 2 hrs Rattus norvegicus 33.3 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, po administered 30 mins before carrageenan challenge measured after 3 hrs Rattus norvegicus 41.7 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, po administered 30 mins before carrageenan challenge measured after 4 hrs Rattus norvegicus 45.8 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, po administered 30 mins before carrageenan challenge measured after 5 hrs Rattus norvegicus 33.3 %
DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) Homo sapiens 116.0 nM
DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) None 602.0 nM
Inhibition of human recombinant AKR1C3 assessed as 1-acenaphthenol oxidation by spectrophotometry Homo sapiens 300.0 nM
Inhibition of human recombinant AKR1C2 assessed as 1-acenaphthenol oxidation by spectrophotometry Homo sapiens 220.0 nM
Inhibition of human recombinant AKR1C1 assessed as 1-acenaphthenol oxidation by spectrophotometry Homo sapiens 810.0 nM
Analgesic activity in Mus musculus NMRI (mouse) assessed as inhibition of late phase of formalin-induced nociception at 30 umol/kg, ip administered 30 min before formalin injection relative to control Mus musculus 74.92 %
Analgesic activity in Mus musculus NMRI (mouse) assessed as inhibition of early phase of formalin-induced nociception at 30 umol/kg, ip administered 30 min before formalin injection relative to control Mus musculus 24.08 %
Analgesic activity in po dosed Mus musculus Swiss albino (mouse) assessed as inhibition of acetic acid-induced writhing administered 1 hr prior to acetic acid challenge measured for 20 min relative to control Mus musculus 63.32 %
Anti-inflammatory activity in Rattus norvegicus Wistar albino (rat) assessed as inhibition of carrageenan-induced paw edema at 80 mg/kg, po measured at 24 hr relative to control Rattus norvegicus 69.06 %
Anti-inflammatory activity in Rattus norvegicus Wistar albino (rat) assessed as inhibition of carrageenan-induced paw edema at 80 mg/kg, po measured at 6 hr relative to control Rattus norvegicus 64.07 %
Anti-inflammatory activity in Rattus norvegicus Wistar albino (rat) assessed as inhibition of carrageenan-induced paw edema at 80 mg/kg, po measured at 4 hr relative to control Rattus norvegicus 50.59 %
Anti-inflammatory activity in Rattus norvegicus Wistar albino (rat) assessed as inhibition of carrageenan-induced paw edema at 80 mg/kg, po measured at 3 hr relative to control Rattus norvegicus 48.84 %
Inhibition of superoxide dismutase level in Rattus norvegicus (rat) stomach at 800 mg/kg, po after 12 hr (Rvb = 37.096 +/- 7.335%) Rattus norvegicus 24.21 %
Analgesic activity in Swiss Mus musculus (mouse) assessed as inhibition of acetic acid-induced abdominal writhing at 13 mg/kg, po administered 1 hr prior to acetic acid injection measured for 10 min Mus musculus 61.1 %
Anti-inflammatory activity in Wistar albino Rattus norvegicus (rat) assessed as inhibition of carrageenan-induced paw edema at 13 mg/kg, po administered 1 hr prior to carrageenan injection measured after 8 hr by mercury plethysmometer (Rvb = 0%) Rattus norvegicus 20.0 %
Anti-inflammatory activity in Wistar albino Rattus norvegicus (rat) assessed as inhibition of carrageenan-induced paw edema at 13 mg/kg, po administered 1 hr prior to carrageenan injection measured after 6 hr by mercury plethysmometer (Rvb = 0%) Rattus norvegicus 24.29 %
Anti-inflammatory activity in Wistar albino Rattus norvegicus (rat) assessed as inhibition of carrageenan-induced paw edema at 13 mg/kg, po administered 1 hr prior to carrageenan injection measured after 4 hr by mercury plethysmometer (Rvb = 0%) Rattus norvegicus 35.58 %
Anti-inflammatory activity in Wistar albino Rattus norvegicus (rat) assessed as inhibition of carrageenan-induced paw edema at 13 mg/kg, po administered 1 hr prior to carrageenan injection measured after 3 hr by mercury plethysmometer (Rvb = 0%) Rattus norvegicus 53.14 %
Anti-inflammatory activity in Wistar albino Rattus norvegicus (rat) assessed as inhibition of carrageenan-induced paw edema at 13 mg/kg, po administered 1 hr prior to carrageenan injection measured after 2 hr by mercury plethysmometer (Rvb = 0%) Rattus norvegicus 52.22 %
Anti-inflammatory activity in Wistar albino Rattus norvegicus (rat) assessed as inhibition of carrageenan-induced paw edema at 13 mg/kg, po administered 1 hr prior to carrageenan injection measured after 1 hr by mercury plethysmometer (Rvb = 0%) Rattus norvegicus 38.41 %
Inhibition of AKR1C3 (unknown origin) Homo sapiens 560.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 63.23 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 72.63 %
Antiinflammatory activity in rat assessed as reduction of carrageenan-induced paw oedema at 0.15 mmol/kg, ip administered 5 mins before carrageenan challenge measured after 3.5 hrs Rattus norvegicus 44.0 %
Anti-inflammatory activity in rat assessed as reduction of carrageenan-induced paw edema at 150 umol/kg, ip after 3.5 hrs relative to control Rattus norvegicus 44.0 %
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 100.0 nM
Inhibition of recombinant MPO (unknown origin) assessed as reduction in taurine chloramine production preincubated with enzyme and taurine followed by H2O2 addition measured after 5 mins Homo sapiens 980.0 nM
Inhibition of acid-induced wild type transthyretin (unknown origin) aggregation expressed in Escherichia coli pre-incubated for 30 mins before acid addition and further incubated for 72 hrs at 37 degC under dark conditions by UV-Vis spectrophotometry Homo sapiens 93.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 15.6 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 6.03 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 12.13 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 13.19 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 30.29 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 7.85 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 2.83 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 8.85 %
Inhibition of NAPRT (unknown origin) Homo sapiens 0.05 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 8.34 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 33.32 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.21 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.16 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.16 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.21 %
Inhibition of recombinant human PDE4B expressed in baculovirus infected Sf9 cells at 10 uM using [3H] cAMP as substrate after 30 min by scintillation proximity assay relative to control Homo sapiens 38.91 %
Inhibition of PDE4D2 (unknown origin) at 30 uM relative to control Homo sapiens 35.54 %
Inhibition of COX-1 (unknown origin) Homo sapiens 186.34 ug.mL-1
Inhibition of COX-2 (unknown origin) Homo sapiens 25.21 ug.mL-1

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Serbia
Slovenia

Cross References

Resources Reference
ChEBI 6717
ChEMBL CHEMBL686
DrugBank DB00784
DrugCentral 1663
FDA SRS 367589PJ2C
Human Metabolome Database HMDB0014922
Guide to Pharmacology 2593
KEGG C02168
PDB ID8
PharmGKB PA450347
PubChem 4044
SureChEMBL SCHEMBL3544
ZINC ZINC000000020241
CONTENTS