OXAPROZIN

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC M01AE12
UNII MHJ80W9LRB
EPA CompTox DTXSID1045118

Structure

InChI Key OFPXSFXSNFPTHF-UHFFFAOYSA-N
Smiles O=C(O)CCc1nc(-c2ccccc2)c(-c2ccccc2)o1
InChI
InChI=1S/C18H15NO3/c20-16(21)12-11-15-19-17(13-7-3-1-4-8-13)18(22-15)14-9-5-2-6-10-14/h1-10H,11-12H2,(H,20,21)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H15NO3
Molecular Weight 293.32
AlogP 4.03
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 63.33
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 22.0

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase inhibitor INHIBITOR PubMed PubMed PubMed PubMed PubMed DailyMed
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
- 110 - - -
Enzyme Protease Serine protease Serine protease SC clan Serine protease S33 family
- 35500 - - -
Enzyme
- 110 - - -
Secreted protein
- - 640 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 323
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 12000 - - -
Assay Description Organism Bioactivity Reference
Fold increase in IC50 vs chymotrypsinogen with saponin None 2.0
Fold increase in IC50 vs malate dehydrogenase (MDH) with 1 mg/ml saponin None 50.0
Fold decrease in IC50 vs malate dehydrogenase (MDH) on pre-incubation None 50.0
Fold increase in IC50 vs chymotrypsinogen with 10x increased enzyme Escherichia coli 50.0
DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) Homo sapiens 856.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 322.54 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 71.47 %
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 10.43 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 2.77 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 16.28 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 23.23 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 21.17 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 18.94 %
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 -4.51 %
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 -2.41 %
Binding affinity to human C5a assessed as dissociation constant after 1 hr by circular dichroism analysis Homo sapiens 640.0 nM
Inhibition of COX1 in A23187-stimulated human platelets assessed as reduction in TXA2 production Homo sapiens 740.0 nM
Inhibition of COX2 in LPS-stimulated human monocytes assessed as reduction in PGE2 production by LC-tandem MIS analysis Homo sapiens 110.0 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 8.24 %
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 -0.2 % 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 -0.2 %

Cross References

Resources Reference
ChEBI 7822
ChEMBL CHEMBL1071
DrugBank DB00991
DrugCentral 2013
FDA SRS MHJ80W9LRB
Human Metabolome Database HMDB0015126
Guide to Pharmacology 7252
KEGG C07356
PharmGKB PA450730
PubChem 4614
SureChEMBL SCHEMBL3286
ZINC ZINC000049643479
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