NIMESULIDE

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Synonyms
Status
Molecule Category Free-form
ATC M01AX17 M02AA26
UNII V4TKW1454M
EPA CompTox DTXSID3037250

Structure

InChI Key HYWYRSMBCFDLJT-UHFFFAOYSA-N
Smiles CS(=O)(=O)Nc1ccc([N+](=O)[O-])cc1Oc1ccccc1
InChI
InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H12N2O5S
Molecular Weight 308.31
AlogP 2.76
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 98.54
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Inhibitory activity was evaluated against human Prostaglandin G/H synthase 2 was determined None 15.0 nM
Percent inhibition of edema in carrageenan-induced rat paw edema was determined by comparing with vehicle control group when tested on 5 rats at peroral dose of 100 umol/Kg Rattus norvegicus 61.7 %
Percent inhibition of pleural inflammation in carrageenan-induced rat model was determined by comparing with vehicle control group when tested on 8 rats at peroral dose of 100 umol/Kg Rattus norvegicus 29.9 %
In vitro inhibition activity against cyclooxygenase 2 with the compound dissolved in DMSO Homo sapiens 600.0 nM
Inhibition of COX2 in human whole blood assessed as inhibition of LPS-stimulated PGE2 production Homo sapiens 700.0 nM
Antiinflammatory activity against carrageenan-induced oedema in Wistar rat paw at 3 mg/kg, ip after 3 hrs relative to control Rattus norvegicus 23.71 %
Antiinflammatory activity against carrageenan-induced oedema in Wistar rat paw at 10 mg/kg, ip after 3 hrs relative to control Rattus norvegicus 40.2 %
Antiinflammatory activity against carrageenan-induced oedema in Wistar rat paw at 30 mg/kg, ip after 3 hrs relative to control Rattus norvegicus 44.32 %
Antiinflammatory activity against carrageenan-induced paw edema in Wistar rat at 300 umol/kg, po after 3 hrs Rattus norvegicus 57.5 %
Antiinflammatory activity against TPA-induced ear edema in Swiss mouse at 300 umol/kg, po after 6 hrs Mus musculus -10.6 %
Antiinflammatory activity against AA-induced ear edema in Swiss mouse at 300 umol/kg, po after 1 hr Mus musculus 100.0 %
Antihyperalgesic effect against formalin-induced pain in mouse at 100 umol/kg, po assessed as licking activity in neurogenic phase Mus musculus 9.3 %
Antihyperalgesic effect against formalin-induced pain in mouse at 100 umol/kg, po assessed as licking activity in inflammatory phase Mus musculus 70.3 %
Inhibition of sheep COX2 at 50 uM Ovis aries 50.0 %
Inhibition of COX2 at 0.1 mM None 7.0 %
Inhibition of COX1 at 0.01 mM None 76.0 %
Inhibition of COX2 in LPS-stimulated human whole blood assessed as PGE2 production by enzyme immunoassay Homo sapiens 700.0 nM
Antiinflammatory activity against gamma carrageenan-induced pleurisy in Wistar rat assessed as inhibition of exudate production in pleural cavity at 5 mg/kg, ip administered 30 mins before gamma carrageenan challenge measured after 4 hrs Rattus norvegicus 31.05 %
Antiinflammatory activity against gamma carrageenan-induced pleurisy in Wistar rat assessed as inhibition of exudate production in pleural cavity at 10 mg/kg, ip administered 30 mins before gamma carrageenan challenge measured after 4 hrs Rattus norvegicus 48.44 %
Antiinflammatory activity against gamma carrageenan-induced pleurisy in Wistar rat assessed as inhibition of exudate production in pleural cavity at 20 mg/kg, ip administered 30 mins before gamma carrageenan challenge measured after 4 hrs Rattus norvegicus 61.53 %
Antiinflammatory activity in albino rat assessed as inhibition of carrageenan-induced paw oedema at 50 mg/kg, po measured after 30 mins of carrageenan challenge relative to control Rattus norvegicus 15.3 %
Antiinflammatory activity in albino rat assessed as inhibition of carrageenan-induced paw oedema at 50 mg/kg, po measured after 60 mins of carrageenan challenge relative to control Rattus norvegicus 26.6 %
Antiinflammatory activity in albino rat assessed as inhibition of carrageenan-induced paw oedema at 50 mg/kg, po measured after 120 mins of carrageenan challenge relative to control Rattus norvegicus 41.1 %
Antiinflammatory activity in albino rat assessed as inhibition of carrageenan-induced paw oedema at 50 mg/kg, po measured after 180 mins of carrageenan challenge relative to control Rattus norvegicus 44.4 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of carrageenan-induced paw edema at 4 mg/kg, po administered 30 mins before carrageenan challenge measured after 30 mins relative to control Rattus norvegicus 37.0 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of carrageenan-induced paw edema at 4 mg/kg, po administered 30 mins before carrageenan challenge measured after 60 mins relative to control Rattus norvegicus 43.0 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of carrageenan-induced paw edema at 4 mg/kg, po administered 30 mins before carrageenan challenge measured after 90 mins relative to control Rattus norvegicus 45.0 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of carrageenan-induced paw edema at 4 mg/kg, po administered 30 mins before carrageenan challenge measured after 120 mins relative to control Rattus norvegicus 36.0 %
Inhibition of ovine COX2 assessed as PGF2alpha level by EIA Ovis aries 400.0 nM
Inhibition of purified COX2 assessed as formation of oxidized TMPD during reduction og PGG2 to PGH2 preincubated for 15 mins by chromogenic assay None 23.0 nM
Antiinflammatory activity in rat assessed as inhibition of paw edema at 10 mg/kg Rattus norvegicus 58.0 %
Inhibition of COX2 None 700.0 nM
Anti-inflammatory activity in Rattus norvegicus Wistar albino (rat) assessed as inhibition of carrageenan-induced paw edema after 180 min (Rvb = 22.3%) Rattus norvegicus 2.54 %
Anti-inflammatory activity in Rattus norvegicus Wistar albino (rat) assessed as inhibition of carrageenan-induced paw edema after 60 min (Rvb = 38.7%) Rattus norvegicus 7.9 %
Anti-inflammatory activity in Rattus norvegicus Wistar albino (rat) assessed as inhibition of carrageenan-induced paw edema after 30 min (Rvb = 30.1%) Rattus norvegicus 10.8 %
Inhibition of COX-2 (unknown origin)-mediated TMPD oxidation using PGG2 as substrate at 100 uM incubated 15 mins prior to substrate addition measured after 36 secs by spectrophotometric analysis Homo sapiens 89.8 %
Inhibition of COX-1 (unknown origin)-mediated TMPD oxidation using PGG2 as substrate at 100 uM incubated 15 mins prior to substrate addition measured after 36 secs by spectrophotometric analysis Homo sapiens 60.2 %
Inhibition of bovine brain tubulin polymerization at 100 uM after 20 mins by spectrophotometric analysis relative to control in presence of GTP Bos taurus 14.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 82.48 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 58.26 %
Antiinflammatory activity in Wistar rat lambda carrageenan-induced pleurisy model assessed as decrease in exudate volume at 20 mg/kg, ip pretreated for 30 mins followed by lambda carrageenan-challenge measured after 4 hrs relative to control Rattus norvegicus 61.53 %
Antiinflammatory activity in Wistar rat lambda carrageenan-induced pleurisy model assessed as decrease in exudate volume at 10 mg/kg, ip pretreated for 30 mins followed by lambda carrageenan-challenge measured after 4 hrs relative to control Rattus norvegicus 48.44 %
Antiinflammatory activity in Wistar rat lambda carrageenan-induced pleurisy model assessed as decrease in exudate volume at 5 mg/kg, ip pretreated for 30 mins followed by lambda carrageenan-challenge measured after 4 hrs relative to control Rattus norvegicus 31.05 %
Inhibition of COX-2 in human whole blood assessed as PGE2 level in plasma after 5 mins by enzyme immunoassay Homo sapiens 700.0 nM
Inhibition of human recombinant COX-2 assessed as PGF2-alpha formation using arachidonic acid as substrate at 20 uM by enzyme immunoassay Homo sapiens 100.0 %
Inhibition of LPS/IFN-gamma-induced PGE2 production in mouse RAW264.7 cells after 17 to 20 hrs by enzyme immunoassay Mus musculus 78.0 nM
Inhibition of LPS/IFN-gamma-induced PGE2 production in PMA-treated human U937 cells after 17 to 20 hrs by enzyme immunoassay Homo sapiens 78.0 nM
Inhibition of LPS/IFN-gamma-induced PGE2 production in mouse RAW264.7 cells at 5 uM after 17 to 20 hrs by enzyme immunoassay relative to control Mus musculus 66.0 %
Inhibition of LPS/IFN-gamma-induced PGE2 production in PMA-treated human U937 cells at 5 uM after 17 to 20 hrs by enzyme immunoassay relative to control Homo sapiens 89.0 %
Inhibition of recombinant His-tagged PDE4B1 (unknown origin) expressed in baculovirus infected sf9 cells at 10 uM using cAMP as substrate preincubated for 15 mins followed by cAMP addition measured after 1 hr by PDE light HTS assay relative to control Homo sapiens 52.0 %
Inhibition of human COX2 expressed in baculovirus infected sf9 microsomes at 10 uM using arachidonic acid as substrate preincubated for 15 mins followed by substrate addition by TMPD oxidation based assay relative to control Homo sapiens 90.0 %
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 2.52 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -0.4225 %
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 -0.13 % 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 -0.13 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate at 1000 uM measured after 10 mins by fluorometric based multimode microplate reader relative to control Homo sapiens 97.82 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate at 100 uM measured after 10 mins by fluorometric based multimode microplate reader relative to control Homo sapiens 89.58 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate at 10 uM measured after 10 mins by fluorometric based multimode microplate reader relative to control Homo sapiens 78.69 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate at 1 uM measured after 10 mins by fluorometric based multimode microplate reader relative to control Homo sapiens 48.28 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate at 0.1 uM measured after 10 mins by fluorometric based multimode microplate reader relative to control Homo sapiens 32.98 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate at 0.01 uM measured after 10 mins by fluorometric based multimode microplate reader relative to control Homo sapiens 21.3 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate at 0.001 uM measured after 10 mins by fluorometric based multimode microplate reader relative to control Homo sapiens 14.12 %

Cross References

Resources Reference
ChEBI 44445
ChEMBL CHEMBL56367
DrugBank DB04743
DrugCentral 1935
FDA SRS V4TKW1454M
Guide to Pharmacology 7401
PDB NIM
PharmGKB PA137179528
PubChem 4495
SureChEMBL SCHEMBL24882
ZINC ZINC000004617749
CONTENTS