KETOPROFEN

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC M01AE03 M02AA10
UNII 90Y4QC304K
EPA CompTox DTXSID6020771

Structure

InChI Key DKYWVDODHFEZIM-UHFFFAOYSA-N
Smiles CC(C(=O)O)c1cccc(C(=O)c2ccccc2)c1
InChI
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14O3
Molecular Weight 254.29
AlogP 3.11
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 54.37
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 19.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase inhibitor INHIBITOR PubMed Wikipedia Wikipedia
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 Oxidoreductase
- 26-3800 - - 0-40
Enzyme
- 26-3800 - - 0-40
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- - - - 64
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 112
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Assay Description Organism Bioactivity Reference
In vitro inhibition of rabbit lens aldose reductase at 10e-4 M. Oryctolagus cuniculus 40.0 %
In vitro inhibition of rabbit lens aldose reductase at 10e-5 M. Oryctolagus cuniculus 15.0 %
In vitro inhibition of rabbit lens aldose reductase at 10e-6 M. Oryctolagus cuniculus 0.0 %
In vitro inhibition of cyclooxygenase-1 via inhibition of TXB2 generation in the presence of 1 uM arachidonic acid in human platelet None 2.0 nM
In vitro inhibition of PGE-2 generation by LPS-stimulated monocytes isolated from human blood. None 26.0 nM
Percent inhibition of edema was measured by adjuvant arthritis paw edema (rat) assay Rattus norvegicus 200.0 nM
Antiinflammatory efficacy is measured by the percent inhibition of paw volume during the 3 week adjuvant arthritis test at 0.002 mM/kg (0.51 mg) Rattus norvegicus 68.0 %
Antiinflammatory efficacy is measured by the percent inhibition of paw volume during the 3 week adjuvant arthritis test at 0.006 mM/kg (0.152 mg) Rattus norvegicus 31.0 %
Antiinflammatory efficacy is measured by the percent inhibition of paw volume during the 3 week adjuvant arthritis test at 0.009 mM/kg (2.29 mg) Rattus norvegicus 82.0 %
The mean increase in paw volume was compared between drug treated groups and placebo to calculate the percent inhibition in rats at 0.02 mmol/kg by carrageenan Edema Assay; 60-69 Rattus norvegicus 60.0 %
The percent inhibition was calculated from the average differences in hind paw volume between the adjuvant injected controls and the adjuvant-injected medicated rats at 0.08 mmol/kg; 0.009-82 Rattus norvegicus 0.009 %
In vitro inhibitory activity against ovine cyclooxygenase-1 (COX-1) at 200 uM; Inactive None 50.0 %
Inhibition of CXCL8-induced chemotaxis of human polymorphonuclear cells at 10e-8 M Homo sapiens 64.0 %
Inhibition of recombinant human AKR1C3 at 50 uM Homo sapiens 12.0 %
Inhibition of COX1 in human whole blood Homo sapiens 330.0 nM
Inhibition of COX2 in human whole blood Homo sapiens 690.0 nM
Antiproliferative activity against human PC3 cells at 100 uM after 72 hrs by MTT assay Homo sapiens 0.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -9.4 %
Inhibition of ovine cyclooxygenase 1 assessed as prostaglandin F2alpha level at 10 uM by enzyme immunoassay relative to control Ovis aries 16.0 %
Inhibition of human recombinant cyclooxygenase 2 assessed as prostaglandin F2alpha level at 10 uM by enzyme immunoassay relative to control Homo sapiens 41.0 %
Antioxidant activity assessed as inhibition of lipid peroxidation at 100 uM None 69.3 %
DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) Homo sapiens 14.0 nM
DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) None 785.0 nM
TP_TRANSPORTER: inhibition of MTX uptake in Xenopus laevis oocytes Xenopus laevis 500.0 nM
TP_TRANSPORTER: inhibition of PAH uptake (PAH: 2 uM, Ketoprofen: 1000 uM) in Xenopus laevis oocytes Xenopus laevis 100.0 %
Antioxidant activity assessed as inhibition of AAPH-induced lipid peroxidation at 1 X 10'-4 M None 69.3 %
Antioxidant activity assessed as DPPH radical scavenging activity at 1 X 10'-4 M after 60 min None 7.2 %
Antioxidant activity assessed as DPPH radical scavenging activity at 1 X 10'-4 M after 20 min None 8.1 %
Antioxidant activity assessed as DPPH radical scavenging activity at 5 X 10'-5 M after 60 min None 3.1 %
Antioxidant activity assessed as DPPH radical scavenging activity at 5 X 10'-5 M after 20 min None 6.4 %
Inhibition of Homo sapiens (human) recombinant cyclooxygenase-2 assessed as formation of PGF2a at 200 uM by enzyme immunoassay Homo sapiens 78.0 %
Inhibition of Ovis aries (sheep) COX1 assessed as formation of PGF2a at 200 uM by enzyme immunoassay Ovis aries 86.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 119.22 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 112.11 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of adjuvant-induced arthritis at 2 mg/kg, po administered for 14 days prior to adjuvant challenge relative to control Rattus norvegicus 84.0 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of adjuvant-induced arthritis at 1 mg/kg, po administered for 14 days followed by adjuvant challenge relative to control Rattus norvegicus 42.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, ip administered prior to carrageenan challenge measured at 1 hr by plethysmometric analysis relative to control Mus musculus 66.7 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, ip administered prior to carrageenan challenge measured at 2 hrs by plethysmometric analysis relative to control Mus musculus 70.7 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, ip administered prior to carrageenan challenge measured at 3 hrs by plethysmometric analysis relative to control Mus musculus 77.4 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 25 mg/kg, ip administered prior to carrageenan challenge measured at 1 hr by plethysmometric analysis relative to control Mus musculus 20.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 25 mg/kg, ip administered prior to carrageenan challenge measured at 2 hrs by plethysmometric analysis relative to control Mus musculus 55.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 25 mg/kg, ip administered prior to carrageenan challenge measured at 3 hrs by plethysmometric analysis relative to control Mus musculus 67.3 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg, ip administered prior to carrageenan challenge measured at 1 hr by plethysmometric analysis relative to control Mus musculus 26.7 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg, ip administered prior to carrageenan challenge measured at 2 hrs by plethysmometric analysis relative to control Mus musculus 55.1 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg, ip administered prior to carrageenan challenge measured at 3 hrs by plethysmometric analysis relative to control Mus musculus 62.7 %
Inhibition of purified ovine COX1 pre-treated for 1 hr before 10-acetyl-3,7-dihydroxyphenoxazin substrate addition in absence of porcine liver esterase by fluorescence assay Ovis aries 800.0 nM
Inhibition of purified ovine COX1 at saturation drug level pre-treated for 1 hr before 10-acetyl-3,7-dihydroxyphenoxazin substrate addition in absence of porcine liver esterase by fluorescence assay Ovis aries 100.0 %
Inhibition of human recombinant COX2 at saturation drug level pre-treated for 1 hr before 10-acetyl-3,7-dihydroxyphenoxazin substrate addition in absence of porcine liver esterase by fluorescence assay Homo sapiens 100.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, po administered prior to carrageenan challenge measured after 1 hr by plethysmometry relative to control Mus musculus 67.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, po administered prior to carrageenan challenge measured after 2 hrs by plethysmometry relative to control Mus musculus 71.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, po administered prior to carrageenan challenge measured after 3 hrs by plethysmometry relative to control Mus musculus 77.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 25 mg/kg, po administered prior to carrageenan challenge measured after 1 hr by plethysmometry relative to control Mus musculus 20.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 25 mg/kg, po administered prior to carrageenan challenge measured after 2 hrs by plethysmometry relative to control Mus musculus 54.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 25 mg/kg, po administered prior to carrageenan challenge measured after 3 hrs by plethysmometry relative to control Mus musculus 67.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg, po administered prior to carrageenan challenge measured after 1 hr by plethysmometry relative to control Mus musculus 27.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg, po administered prior to carrageenan challenge measured after 2 hrs by plethysmometry relative to control Mus musculus 55.0 %
Antiinflammatory activity in albino Swiss mouse assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg, po administered prior to carrageenan challenge measured after 3 hrs by plethysmometry relative to control Mus musculus 63.0 %
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 47.0 %
Inhibition of Ovine COX-1 preincubated for 15 mins by fluorescence analysis Ovis aries 67.0 nM
Inhibition of recombinant human COX-2 preincubated for 15 mins by fluorescence analysis Homo sapiens 61.0 nM
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 47.0 %
Antiinflammatory activity against albino rat assessed as inhibition of carrageenin induced paw edema at 100 mg/kg, po administered for 1 hr followed by carrageenin challenge measured after 4 hrs Rattus norvegicus 63.0 %
Antinociceptive activity in Swiss mouse assessed as inhibition of capsaicin induced nociception by measuring paw licking time at 100 mg/kg administered via oral gavage for 1 hr followed by capsaicin challenge measured for 5 mins post dose relative to control Mus musculus 81.0 %
Antinociceptive activity in Swiss mouse assessed as inhibition of capsaicin-induced nociception at 100 mg/kg, po administered 1 hr followed by capsaicin challenge measured for 5 mins relative to vehicle-treated control Mus musculus 80.0 %
Antinociceptive activity in Swiss mouse assessed as inhibition of CFA-induced mechanical allodynia at 100 mg/kg, po after 2 hrs relative to vehicle-treated control Mus musculus 65.0 %
Inhibition of ovine COX1 assessed as reduction in PGH2 production by enzyme immunoassay Ovis aries 110.0 nM
Inhibition of ovine COX2 assessed as reduction in PGH2 production by enzyme immunoassay Ovis aries 180.0 nM
Anti-inflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, ip measured at 1 hr post dose relative to control Rattus norvegicus 23.3 %
Anti-inflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, ip measured at 2 hrs post dose relative to control Rattus norvegicus 54.2 %
Anti-inflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 20 mg/kg, ip measured at 3 hrs post dose relative to control Rattus norvegicus 66.0 %
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 6.88 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -2.29 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 8.94 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 8.02 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 24.16 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 5.45 %
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 -5.87 %
Inhibition of COX1 in human platelet rich plasma in assessed as inhibition of ADP-induced platelet aggregation at 10 uM incubated for 5 mins by turbidimetry based Born's method relative to control Homo sapiens 25.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.21 %
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 0.0 % 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 0.0 %

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Slovakia
Slovenia
Sweden

Cross References

Resources Reference
ChEBI 6128
ChEMBL CHEMBL571
DrugBank DB01009
DrugCentral 1528
FDA SRS 90Y4QC304K
Human Metabolome Database HMDB0015144
Guide to Pharmacology 4795
KEGG C01716
PharmGKB PA450149
PubChem 3825
SureChEMBL SCHEMBL2896
ZINC ZINC00005560
CONTENTS