NAPROXEN

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC G02CC02 M01AE02 M02AA12
UNII 57Y76R9ATQ
EPA CompTox DTXSID4040686

Structure

InChI Key CMWTZPSULFXXJA-VIFPVBQESA-N
Smiles COc1ccc2cc([C@H](C)C(=O)O)ccc2c1
InChI
InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H14O3
Molecular Weight 230.26
AlogP 3.04
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 46.53
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase inhibitor INHIBITOR PubMed PubMed 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
- 1200 - - 64
Enzyme Isomerase
- 13000 - - -
Enzyme Oxidoreductase
- 61-52200 - - 55-88
Enzyme Protease Aspartic protease Aspartic protease AD clan Aspartic protease A22A subfamily Aspartic protease A22A regulatory subfamily
- - - - 3
Enzyme
- 61-52200 - - 55-88
Ion channel Other ion channel Miscellaneous ion channel Presenilin ER Ca2+ leak channel family
- - - - 3
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- - - - 35
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 104
Assay Description Organism Bioactivity Reference
Inhibition of proliferation measured by inhibition of [3H]thymidine incorporation by HMVEC-L cells Homo sapiens 50.0 ug
In vitro inhibitory activity against Prostaglandin G/H synthase in rat neutrophils None 60.0 nM
Compound was tested in vitro for inhibition of human platelet Prostaglandin G/H synthase 1 at 10 uM None 350.0 nM
Analgesic activity (50 mg/kg, sc)in phenylquinone-induced abdominal constriction assay(PAC) Rattus norvegicus 54.0 %
Compound was tested in vivo for antiinflammatory activity against chronic adjuvant arthritic rat by prophylactic inhibition 2 degree paw after peroral administration of 1 mg/kg of dose Rattus norvegicus 14.0 %
Compound was tested in vivo for antiinflammatory activity against chronic adjuvant arthritic rat by therapeutic inhibition 2 degree paw after peroral administration of 0.3 mg/kg of dose Rattus norvegicus 27.0 %
Compound was tested in vivo for antiinflammatory activity against chronic adjuvant arthritic rat by therapeutic inhibition 2 degree paw after peroral administration of 1 mg/kg of dose Rattus norvegicus 50.0 %
Compound was tested in vivo for antiinflammatory activity against chronic adjuvant arthritic rat by therapeutic inhibition 2 degree paw after peroral administration of 25 mg/kg of dose Rattus norvegicus 58.0 %
Compound was tested in vivo for antiinflammatory activity against chronic adjuvant arthritic rat by therapeutic inhibition 2 degree paw after peroral administration of 3 mg/kg of dose Rattus norvegicus 70.0 %
Compound was tested in vivo for antiinflammatory activity against chronic adjuvant arthritic rat by therapeutic inhibition 2 degree paw after peroral administration of 5 mg/kg of dose Rattus norvegicus 44.0 %
Percent inhibition was determined in vivo in male Dawley rats at a dose of 10 mg/kg by rat carrageenan-induced hyperalgesia assay Rattus norvegicus 66.0 %
In vitro inhibitory activity against ovine cyclooxygenase-1 (COX-1) at 200 uM; Inactive None 50.0 %
Inhibition of lipopolysaccharide-induced PGE-2 production at 10e-5 M Mus musculus 99.0 %
Inhibition of CXCL8-induced chemotaxis of human polymorphonuclear cells at 10e-8 M Homo sapiens 35.0 %
Inhibition of recombinant human AKR1C3 Homo sapiens 480.0 nM
Anti-inflammatory activity against paw edema induced by carrageenan in fischer rat at 300 umol/kg, ip Rattus norvegicus 51.0 %
Inhibition of beta amyloid protein 42 in SH-SY5Y cell lines overexpressing SPA4CT at 300 uM Homo sapiens 3.0 %
Inhibition of carrageenan-induced paw edema in Sprague-Dawley rat at 10 mg/kg, po Rattus norvegicus 68.3 %
Antiinflammatory activity against carrageenan-induced paw edema in rat at 30 mg/kg, po after 4 hrs Rattus norvegicus 81.81 %
Analgesic activity in rat at 30 mg/kg, po Rattus norvegicus 73.5 %
Inhibition of COX1 at 100 uM None 39.3 %
Antiinflammatory activity against carrageenan-induced paw edema in Sprague-Dawley rat at 10 mg/kg, iv Rattus norvegicus 50.0 %
Inhibition of IgE-specific antigen-induced PGF2alpha release in rat MC9 cells at 0.20 uM Rattus norvegicus 50.0 %
Inhibition of arachidonic acid-induced PGF2-alpha release in rat MC9 cells at 0.33 uM Rattus norvegicus 50.0 %
Inhibition of sheep COX1 at 2.52 ug/mL Ovis aries 57.96 %
Antiinflammatory activity in mouse assessed as inhibition of phorbol myristyl palmitate-induced ear lobe edema at 0.1 umol/ear after 6 hrs relative to control Mus musculus 28.0 %
Antiinflammatory activity in mouse assessed as inhibition of phorbol myristyl palmitate-induced ear lobe edema at 0.1 umol/ear after 24 hrs relative to control Mus musculus 21.0 %
Antiinflammatory activity in mouse assessed as inhibition of phorbol myristyl palmitate-induced ear lobe edema at 0.1 umol/ear after 48 hrs relative to control Mus musculus 18.0 %
Antiinflammatory activity in mouse assessed as inhibition of phorbol myristyl palmitate-induced ear lobe edema at 1 umol/ear after 6 hrs relative to control Mus musculus 45.0 %
Antiinflammatory activity in mouse assessed as inhibition of phorbol myristyl palmitate-induced ear lobe edema at 1 umol/ear after 48 hrs relative to control Mus musculus 25.0 %
Antiinflammatory activity in mouse assessed as inhibition of phorbol myristyl palmitate-induced ear lobe edema at 1 umol/ear after 24 hrs relative to control Mus musculus 36.0 %
Inhibition of HSL in Wistar rat isolated fat cells at 10 uM by spectrophotometric assay Rattus norvegicus 64.0 %
Inhibition of carrageenan-induced paw edema in Sprague-Dawley rat administered 2 hrs before carrageenan challenge at 10 mg/kg, po Rattus norvegicus 50.0 %
Inhibition of PGF2alpha production in mouse MC9 cells Mus musculus 200.0 nM
Inhibition of PGF2apha production in arachidonic acid-stimulated mouse MC9 cells Mus musculus 330.0 nM
Inhibition of ovine COX1 at 100 uM Ovis aries 72.0 %
Inhibition of human recombinant COX2 at 100 uM Homo sapiens 86.0 %
Inhibition of recombinant Curvularia lunata trihydroxynaphthalene reductase Cochliobolus lunatus 9.0 %
Antiinflammatory activity in Albino mouse assessed as inhibition of carrageenan-induced foot paw edema at 30 mg/kg, po administered 1 hr before carrageenan challenge measured after 2 hrs Mus musculus 66.9 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 40 mg/kg, po administered 30 mins before carrageenan challenge measured after 0.5 hrs Rattus norvegicus 9.4 % Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 40 mg/kg, po administered 30 mins before carrageenan challenge measured after 0.5 hrs Rattus norvegicus 9.4 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 40 mg/kg, po administered 30 mins before carrageenan challenge measured after 1 hr Rattus norvegicus 16.3 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 40 mg/kg, po administered 30 mins before carrageenan challenge measured after 2 hrs Rattus norvegicus 28.1 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 40 mg/kg, po administered 30 mins before carrageenan challenge measured after 3 hrs Rattus norvegicus 46.9 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 40 mg/kg, po administered 30 mins before carrageenan challenge measured after 4 hrs Rattus norvegicus 37.5 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 40 mg/kg, po administered 30 mins before carrageenan challenge measured after 5 hrs Rattus norvegicus 18.8 %
Binding affinity to beta-amyloid plaques None 5.7 nM
Inhibition of ovine COX-1 Ovis aries 180.0 nM
Antiinflammatory activity in rat assessed as inhibition of complete Freund's adjuvant-induced paw withdrawal threshold at 20 mg/kg, sc after 60 mins (Rvb = 4.8%) Rattus norvegicus 23.9 %
Binding affinity to amyloid beta fibrils None 5.7 nM
DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) Homo sapiens 211.0 nM
Inhibition of human recombinant COX-2 assessed as PGF2alpha production at 200 uM by enzyme immunoassay Homo sapiens 68.0 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 30 mg/kg after 2 hrs Rattus norvegicus 71.7 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of carageenaan-induced paw edema at 45 mg/kg, po administered 1 hr prior to carageenaan-challenge measured at 4 hrs relative to control Rattus norvegicus 81.23 %
Antiinflammatory activity in Wistar albino rat assessed as inhibition of carageenaan-induced paw edema at 45 mg/kg, po administered 1 hr prior to carageenaan-challenge measured at 3 hrs relative to control Rattus norvegicus 78.84 %
Anti-inflammatory activity in Rattus norvegicus Wistar (rat) assessed as inhibition of carrageenan-induced edema volume at 50.0 mg/kg, po measured after 120 min Rattus norvegicus 58.0 %
Anti-inflammatory activity in Rattus norvegicus Wistar (rat) assessed as inhibition of carrageenan-induced edema volume at 50.0 mg/kg, po measured after 90 min Rattus norvegicus 42.0 %
Anti-inflammatory activity in Rattus norvegicus Wistar (rat) assessed as inhibition of carrageenan-induced edema volume at 50.0 mg/kg, po measured after 60 min Rattus norvegicus 32.0 %
Analgesic activity in Mus musculus (mouse) assessed as inhibition of acetic acid-induced writhing at 50 mg/kg, po pretreated 1 hr before acetic acid challenge Mus musculus 61.36 %
Anti-inflammatory activity in Rattus norvegicus Wistar (rat) assessed as inhibition of carrageenan-induced edema volume at 50.0 mg/kg, po measured after 30 min Rattus norvegicus 10.0 %
Inhibition of Homo sapiens (human) recombinant cyclooxygenase-2 assessed as formation of PGF2a at 200 uM by enzyme immunoassay Homo sapiens 88.0 %
Inhibition of Ovis aries (sheep) COX1 assessed as formation of PGF2a at 200 uM by enzyme immunoassay Ovis aries 52.0 %
Anti-inflammatory activity in Rattus norvegicus Fischer-344 (rat) assessed as inhibition of carrageenan-induced paw oedema at 0.30 mmol/kg, ip administered 5 min before FCA challenge measured after 3 hr relative to control Rattus norvegicus 51.0 %
Competitive inhibition of human recombinant COX2 assessed as inhibition of PGF2a production at 200 uM by enzyme immunoassay Homo sapiens 65.0 %
Inhibition of ovine COX1 assessed as inhibition of PGF2a production by enzyme immunoassay Ovis aries 46.0 %
Inhibition of ovine COX1 Ovis aries 180.0 nM
Antiinflammatory activity in Duncan Hartley guinea pig assessed as Inhibition of carrageenan-induced PGE2 production at 10 mg/kg, po Cavia porcellus 60.0 %
Antiinflammatory activity in Kunming mouse assessed as inhibition of xylene-induced auricle tumefaction at 200 uM/kg, tid qd for 5 days relative to control Mus musculus 30.63 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 114.77 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 103.46 %
Inhibition of bovine COX-1 assessed as PGF2-alpha formation using arachidonic acid as substrate at 20 uM by enzyme immunoassay Bos taurus 30.0 %
Inhibition of human recombinant COX-2 assessed as PGF2-alpha formation using arachidonic acid as substrate at 20 uM by enzyme immunoassay Homo sapiens 55.0 %
In vivo antiinflammatory activity in mouse assessed as decrease in carrageenan-induced paw edema at 0.30 mmol/kg, ip administered immediately after carrageenan injection measured after 3.5 hrs Mus musculus 51.0 %
Antiinflammatory activity in mouse assessed as inhibition of xylene-induced ear swelling at 150 mg/kg, ig administered 90 mins prior to xylene challenge measured after 30 mins Mus musculus 36.65 %
Antiinflammatory activity in rabbit assessed as inhibition of edema at 200 ug per site by reversed passive arthus test Oryctolagus cuniculus 55.0 %
Antiinflammatory activity in Wistar rat mycobacterial adjuvant-induced arthritis model assessed as inhibition of swelling at 30 mg/kg/day, po measured on day 14 relative to control Rattus norvegicus 65.0 %
Antiinflammatory activity in Wistar rat assessed as inhibition of cotton pellet-induced granuloma formation at 30 mg/kg, po after 5 days relative to control Rattus norvegicus 46.0 %
Antiinflammatory activity in rat assessed as inhibition of carrageenan-induced paw edema at 6 mg/kg, po relative to control Rattus norvegicus 30.0 %
Antinociceptive activity against CD-1 mouse assessed as licking of hind paw or jumping at 100 mg/kg, po after 90 mins Mus musculus 36.0 %
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 11.0 %
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 11.0 %
Inhibition of COX in human Mahlavu cells after 48 hrs by fluorometric assay Homo sapiens 70.0 %
Inhibition of COX in human HuH7 cells after 48 hrs by fluorometric assay Homo sapiens 70.0 %
Binding affinity to Influenza A virus nucleoprotein by surface plasmon resonance analysis influenza A virus 250.0 nM
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 2.49 %
Anti-inflammatory activity in C57BL/6 mouse assessed as inhibition of carrageenan-induced hind paw edema treated immediately after carrageenan challenge measured after 3.5 hrs relative to control Mus musculus 51.0 %
Anti-inflammatory activity in rat assessed as inhibition of carrageenan-induced paw edema relative to control Rattus norvegicus 85.02 %
Inhibition of human recombinant AKR1C3 using S-tetralol as substrate assessed as reduction in NADP+-dependent S-tetralol oxidation preincubated for 10 mins followed by protein addition by fluorometric assay Homo sapiens 180.0 nM
Inhibition of COX1 in ram seminal vesicles using arachidonic acid as substrate assessed as reduction in PGH2 conversion to PGG2 by measuring TMPD oxidation preincubated for 5 mins followed by substrate/TMPD addition measured for 5 mins by colorimetric assay Ovis aries 61.0 nM
Inhibition of COX2 (unknown origin) using arachidonic acid as substrate assessed as reduction in PGH2 conversion to PGG2 by measuring TMPD oxidation preincubated for 5 mins followed by substrate/TMPD addition measured for 5 mins by colorimetric assay Homo sapiens 900.0 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 24.65 %
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 -0.26 % 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 -0.26 %
Antiinflammatory activity in mouse model of xylene-induced ear swelling assessed as inhibition of swelling by measuring weight of the ear at 150 mg/kg, ig pretreated for 90 mins followed by xylene challenge and measured after 30 mins relative to control Mus musculus 25.03 %

Related Entries

Environmental Exposure

Environmental Exposure Map
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Cross References

Resources Reference
ChEBI 7476
ChEMBL CHEMBL154
DrugBank DB00788
DrugCentral 1883
FDA SRS 57Y76R9ATQ
Human Metabolome Database HMDB0001923
Guide to Pharmacology 5230
PDB NPS
PubChem 156391
SureChEMBL SCHEMBL3046
ZINC ZINC000000105216
CONTENTS