DIFLUNISAL

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N02BA11
UNII 7C546U4DEN
EPA CompTox DTXSID5022932

Structure

InChI Key HUPFGZXOMWLGNK-UHFFFAOYSA-N
Smiles O=C(O)c1cc(-c2ccc(F)cc2F)ccc1O
InChI
InChI=1S/C13H8F2O3/c14-8-2-3-9(11(15)6-8)7-1-4-12(16)10(5-7)13(17)18/h1-6,16H,(H,17,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H8F2O3
Molecular Weight 250.2
AlogP 3.04
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 57.53
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 18.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase inhibitor INHIBITOR PubMed 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 Lyase
- 13500 - 2560 -
Enzyme Oxidoreductase
- - - 34000 -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S1A subfamily
- - - - 13
Secreted protein
5600 6300-25000 75-5600 - 98
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 201
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 13.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM None 5.0 %
In vitro inhibitory activity against ovine cyclooxygenase-1 (COX-1) at 200 uM; Inactive None 50.0 %
Antiinflammatory activity against BALB/c mouse assessed as inhibition of carrageenan-induced paw edema at 50 mg/kg, po after 4 hrs Mus musculus 24.2 %
Antiinflammatory activity in mouse assessed as inhibition of xylene-induced ear edema at 40 mg/kg, po Mus musculus 39.85 %
Analgesic activity in Kunming mouse assessed as inhibition of acetic acid-induced writhing response at 40 mg/kg, po Mus musculus 8.33 %
TP_TRANSPORTER: inhibition of Adefovir uptake in OAT1-expressing CHO cells None 850.0 nM
TP_TRANSPORTER: inhibition of PAH uptake (PAH: 2 uM, Diflunisal: 1000 uM) in Xenopus laevis oocytes Xenopus laevis 100.0 %
Inhibition of transthyretin (unknown origin) aggregation at 2 mol equiv measured at 36 hrs by congo red assay relative to control Homo sapiens 90.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 201.02 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 87.47 %
Inhibition of human recombinant TTR Y78F mutant-mediated fibrillogenesis at 40 uM after 30 mins by turbidimetric assay relative to control Homo sapiens 85.0 %
Inhibition of TTR V30M mutant (unknown origin) expressed in Escherichia coli assessed as inhibition of amyloid fibril formation at 20 uM by fluorescence assay Homo sapiens 20.0 %
Binding affinity to TTR (unknown origin) by isothermal titration calorimetric analysis Homo sapiens 580.0 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 98.0 %
Binding affinity to transthyretin (unknown origin) by ITC method Homo sapiens 407.0 nM
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 -11.25 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 6.27 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 3.43 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 7.67 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 12.12 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 13.36 %
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 -3.56 %
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 -4.27 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.379 %
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 0.02 % 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 0.02 %
Binding affinity to wild type TTR (unknown origin) expressed in Escherichia coli BL21/DE3 by Circular dichroism spectroscopy Homo sapiens 75.0 nM

Cross References

Resources Reference
ChEBI 39669
ChEMBL CHEMBL898
DrugBank DB00861
DrugCentral 880
FDA SRS 7C546U4DEN
Human Metabolome Database HMDB0014999
Guide to Pharmacology 7162
KEGG C01691
PDB 1FL
PharmGKB PA449313
PubChem 3059
SureChEMBL SCHEMBL4337
ZINC ZINC000000020243
CONTENTS