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Compound Detail

CHEMBL1316

CARPROFEN
💊 Approved Drug
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💊 Approved Drug
CC(C(=O)O)c1ccc2c(c1)[nH]c1ccc(Cl)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1316
Name CARPROFEN
Phase Approved
Structure Type MOL
InChI Key PUXBGTOOZJQSKH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Carprofen Carprofen for veterinary use Carprofene Carprofeno NSC-297935 Rimadyl RO 20-5720/000 Ro-20-5720-000 RO-20-5720/000
7
Targets
23
Activities
2
Assay Types
3
PK Parameters
20
Publications
9
Known Names
1
Mechanisms

Molecular Properties

273.7
MW (Da)
4.16
ALogP
1
HBA
2
HBD
53.1
PSA (Ų)
0.74
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -profen
USAN Year 1976

Extended Properties

Molecular Formula C15H12ClNO2
MW 273.72
Aromatic Rings 3
Heavy Atoms 19
NP-Likeness -0.08

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase-2 inhibitor INHIBITOR Prostaglandin G/H synthase 2 ✓ ✓

Activity Summary

IC50 22 meas. best 8.28
Kd 1 meas. best 6.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 8.28 5.7967 5.3 3
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 8.28 6.515 5.3 6
Complement C5
CHEMBL2364163
 Kd 6.24 6.24 580.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 5.52 5.52 3000.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 4.89 4.8067 13000.0 3
Fatty-acid amide hydrolase 1
CHEMBL3229
 IC50 4.5 4.305 32000.0 2
Unchecked
CHEMBL612545
 IC50 4.12 4.1167 76000.0 3

Pharmacokinetic Data

Parameter Value Units Species
F 90.0 % Canis lupus familiaris
T1/2 8.0 hr Homo sapiens
Tmax 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 1 IC50 = 5.3 nM 8.28 Inhibition of human COX1 38516587
Prostaglandin G/H synthase 2 IC50 = 5.3 nM 8.28 Inhibition of COX2 (unknown origin) fluorescence based analysis 38516587
Prostaglandin G/H synthase 2 IC50 = 100.0 nM 7.0 Inhibition of human recombinant COX2 after 5 mins 20503989
Prostaglandin G/H synthase 2 IC50 = 102.0 nM 6.99 Inhibitory activity against cell-free canine COX-2 11262075
Prostaglandin G/H synthase 2 IC50 = 102.0 nM 6.99 Inhibition of human recombinant COX-2 assessed as residual activity by measuring... 21873070
Complement C5 Kd = 580.0 nM 6.24 Binding affinity to human C5a assessed as dissociation constant after 1 hr by ci... 31447248
ATP-binding cassette sub-family C member 4 IC50 = 3000.0 nM 5.52 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
Prostaglandin G/H synthase 2 IC50 = 3900.0 nM 5.41 Inhibition of human COX2 pre-incubated for 10 mins before substrate addition by ... 23043222
Prostaglandin G/H synthase 1 IC50 = 13000.0 nM 4.89 Inhibition of ovine COX1 after 5 mins 20503989
Prostaglandin G/H synthase 1 IC50 = 13200.0 nM 4.88 Inhibitory activity against cell-free canine COX-1 11262075
Prostaglandin G/H synthase 1 IC50 = 13200.0 nM 4.88 Inhibition of ovine COX-1 assessed as residual activity by measuring formation o... 21873070
Prostaglandin G/H synthase 1 IC50 = 22300.0 nM 4.65 Inhibition of ovine COX1 pre-incubated for 10 mins before arachidonic acid subst... 23043222
Fatty-acid amide hydrolase 1 IC50 = 32000.0 nM 4.5 Inhibition of rat brain FAAH using [3H]AEA as substrate 28535469
Prostaglandin G/H synthase 2 IC50 = 38000.0 nM 4.42 Inhibition of COX2 in human whole blood 18667313
Prostaglandin G/H synthase 1 IC50 = 59000.0 nM 4.23 Inhibition of COX1 in human whole blood 18667313
Unchecked IC50 = 76000.0 nM 4.12 Inhibition of beta amyloid protein 42 in human H4 cells overexpressing APP695 17181139
Unchecked IC50 = 76000.0 nM 4.12 Inhibition of gamma secretase assessed as reduction in Abeta42 production 21141968
Unchecked IC50 = 78000.0 nM 4.11 Inhibition of beta amyloid protein 38 in human H4 cells overexpressing APP695 17181139
Fatty-acid amide hydrolase 1 IC50 = 78600.0 nM 4.11 Inhibition of FAAH in rat brain homogenates pre-incubated for 10 mins before add... 23043222

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
35295086 10.1021/acsmedchemlett.1c00680 Staphylococcus aureus 9
31447248 10.1016/j.bmc.2019.115052 Complement C5 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
37468498 10.1038/s41467-023-40064-9 Bile acid receptor 4
17181139 10.1021/jm0610200 Unchecked 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 3
37468498 10.1038/s41467-023-40064-9 Androgen receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Retinoic acid receptor gamma 2
37468498 10.1038/s41467-023-40064-9 Retinoic acid receptor beta 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Oxysterols receptor LXR-beta 2
37468498 10.1038/s41467-023-40064-9 Retinoic acid receptor alpha 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Oxysterols receptor LXR-alpha 2

Data from ChEMBL 36 via Core Engine