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Compound Detail

CHEMBL1071

OXAPROZIN
💊 Approved Drug
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💊 Approved Drug
O=C(O)CCc1nc(-c2ccccc2)c(-c2ccccc2)o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1071
Name OXAPROZIN
Phase Approved
Structure Type MOL
InChI Key OFPXSFXSNFPTHF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Coxanto Daypro NSC-310839 Oxaprozin Oxaprozina Oxaprozine WY-21,743 WY-21743
16
Targets
40
Activities
4
Assay Types
6
PK Parameters
20
Publications
8
Known Names
4
Indications
1
Mechanisms

Molecular Properties

293.3
MW (Da)
4.03
ALogP
3
HBA
1
HBD
63.3
PSA (Ų)
0.77
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1973

Extended Properties

Molecular Formula C18H15NO3
MW 293.32
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -0.33

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase ✓ ✓

Indications

Arthritis, Juvenile Arthritis, Rheumatoid Osteoarthritis Rheumatic Diseases

ATC Classification

M01AE12
oxaprozin
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States

Activity Summary

IC50 31 meas. best 6.96
Kd 4 meas. best 6.19
EC50 3 meas. best 4.79
Ki 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.96 5.7 110.0 2
Complement C5
CHEMBL2364163
 Kd 6.19 6.19 640.0 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 6.13 5.9533 740.0 3
Serine hydroxymethyltransferase, mitochondrial
CHEMBL4295747
 IC50 5.71 5.71 1949.8 1
Unchecked
CHEMBL612545
 IC50 5.3 5.15 5000.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.8833 10000.0 6
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.92 4.92 12000.0 1
Nuclear receptor subfamily 4 group A member 2
CHEMBL5002
 IC50 4.92 4.6129 12000.0 7
Nuclear receptor subfamily 4immunitygroup A member 1
CHEMBL1293229
 IC50 4.8 4.7533 16000.0 3
Retinoic acid receptor RXR-alpha
CHEMBL2061
 EC50 4.79 4.79 16100.0 1
Nuclear receptor subfamily 4 group A member 3
CHEMBL1961792
 IC50 4.66 4.66 22000.0 1
Retinoic acid receptor RXR-beta
CHEMBL1870
 EC50 4.6 4.6 25000.0 1
Bifunctional epoxide hydrolase 2
CHEMBL4140
 IC50 4.45 4.45 35500.0 1
Retinoic acid receptor RXR-gamma
CHEMBL2004
 EC50 4.4 4.4 40100.0 1
Bifunctional epoxide hydrolase 2
CHEMBL5669
 IC50 4.2 4.2 62500.0 1
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 4.16 4.16 70000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.07 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 6.46 uL.min-1.(10^6cells)-1 Homo sapiens
Cmax 372000.0 nM -
F 80.0 % Homo sapiens
T1/2 2.35 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 110.0 nM 6.96 Inhibition of COX2 in LPS-stimulated human monocytes assessed as reduction in PG... 31436984
Complement C5 Kd = 640.0 nM 6.19 Binding affinity to human C5a assessed as dissociation constant after 1 hr by ci... 31447248
Prostaglandin G/H synthase 1 IC50 = 740.0 nM 6.13 Inhibition of COX1 in A23187-stimulated human platelets assessed as reduction in... 31436984
Prostaglandin G/H synthase 1 IC50 = 856.0 nM 6.07 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Serine hydroxymethyltransferase, mitochondrial IC50 = 1949.84 nM 5.71 Inhibition of His-tagged human recombinant SHMT2 expressed in Escherichia coli B... -
Prostaglandin G/H synthase 1 IC50 = 2200.0 nM 5.66 Inhibition of COX-1 in human platelet 37148849
Unchecked IC50 = 5000.0 nM 5.3 Inhibition of hexa-His-tagged human soluble epoxide hydrolase N-terminal phospha... 31436984
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 10000.0 nM 5.0 Inverse agonist activity at Gal4-fused human Nurr1 L444F mutant transfected in H... 39081058
ATP-binding cassette sub-family C member 4 IC50 = 12000.0 nM 4.92 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Nuclear receptor subfamily 4 group A member 2 IC50 = 12000.0 nM 4.92 Inverse agonist activity at Gal4-fused human full length Nurr1 monomer transfect... 39081058
Nuclear receptor subfamily 4 group A member 2 IC50 = 12000.0 nM 4.92 Inverse agonist activity at Gal4-fused human full length Nurr1 heterodimer trans... 39081058
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 15848.93 nM 4.8 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 15848.93 nM 4.8 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Nuclear receptor subfamily 4immunitygroup A member 1 IC50 = 16000.0 nM 4.8 Inverse agonist activity at human Nur77 LBD transiently transfected in HEK293T c... 37918435
Nuclear receptor subfamily 4immunitygroup A member 1 IC50 = 16000.0 nM 4.8 Inverse agonist activity at human Nur77 (358 to 598 residues) transfected in HEK... 39081058
Retinoic acid receptor RXR-alpha EC50 = 16100.0 nM 4.79 Agonist activity at human RXRalpha transfected in human HEK293T cells co-express... 33793232

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 68
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
31447248 10.1016/j.bmc.2019.115052 Complement C5 9
39081058 10.1021/acs.jmedchem.4c01218 Nuclear receptor subfamily 4 group A member 2 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
39081058 10.1021/acs.jmedchem.4c01218 Unchecked 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 6
31436984 10.1021/acs.jmedchem.9b00445 Bifunctional epoxide hydrolase 2 6
16019946 10.1080/00498250400028197 ADMET 4
34547896 10.1021/acs.jmedchem.1c00823 Transthyretin 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
36356292 10.1021/acs.jmedchem.2c01168 quadruplex DNA 4
- 10.6019/CHEMBL3301361 ADMET 4
36356292 10.1021/acs.jmedchem.2c01168 Replicase polyprotein 1ab 4
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3

Data from ChEMBL 36 via Core Engine