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Compound Detail

CHEMBL175

DEXIBUPROFEN
💊 Approved Drug
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💊 Approved Drug
CC(C)Cc1ccc([C@H](C)C(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL175
Name DEXIBUPROFEN
Phase Approved
Structure Type MOL
InChI Key HEFNNWSXXWATRW-JTQLQIEISA-N
Therapeutic ✓ Yes

Known Names

(s)-ibuprofen Dexibuprofen Dexibuprofene Dexibuprofeno NSC-759814 S-ibuprofen Seractil
8
Targets
20
Activities
2
Assay Types
16
PK Parameters
20
Publications
7
Known Names
3
Indications
1
Mechanisms

Molecular Properties

206.3
MW (Da)
3.07
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.82
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -profen
USAN Year 1997

Extended Properties

Molecular Formula C13H18O2
MW 206.28
Aromatic Rings 1
Heavy Atoms 15
NP-Likeness 0.14

Mechanism of Action

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

Indications

Rheumatic Diseases Fever Pain

ATC Classification

M01AE14
dexibuprofen
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Activity Summary

IC50 19 meas. best 7.01
Ki 1 meas. best 7.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 7.35 7.35 44.4 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 7.01 6.5233 98.7 3
Interleukin-8 receptors, CXCR1/CXCR2
CHEMBL2096909
 IC50 7.0 7.0 100.0 1
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.14 5.875 730.0 2
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 5.83 5.4033 1480.0 6
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 5.82 5.82 1500.0 1
Aldo-keto reductase family 1 member C3
CHEMBL4681
 IC50 4.49 4.49 32700.0 1
Aldo-keto reductase family 1 member C2
CHEMBL5847
 IC50 4.37 4.37 42400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 33947.26 ng.hr.mL-1 Mus musculus
AUC 34528.94 ng.hr.mL-1 Mus musculus
AUC 81106.68 ng.hr.mL-1 Mus musculus
AUC 81648.09 ng.hr.mL-1 Mus musculus
CL 2.333 mL.min-1.kg-1 Mus musculus
Cmax 167684.7 nM Mus musculus
Cmax 252763.23 nM Mus musculus
F 80.0 % Homo sapiens
F 118.23 % Mus musculus
MRT 1.28 hr Mus musculus
MRT 1.68 hr Mus musculus
T1/2 1.14 hr Mus musculus
T1/2 1.12 hr Mus musculus
Tmax 0.08 hr Mus musculus
Tmax 0.08 hr Mus musculus
Vd 0.24 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 44.4 nM 7.35 Binding affinity to amyloid beta fibrils 21802289
Prostaglandin G/H synthase 1 IC50 = 98.65 nM 7.01 Inhibition of COX1 in human HEL 92.1.7 cells assessed as thromboxane B2 producti... 21602044
Interleukin-8 receptors, CXCR1/CXCR2 IC50 = 100.0 nM 7.0 Inhibition of CXCL8-induced chemotaxis in human polymorphonuclear cells 15974585
Prostaglandin G/H synthase 1 IC50 = 105.0 nM 6.98 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 2 IC50 = 730.0 nM 6.14 Inhibition of COX2 in LPS-stimulated and PMA-treated human U937 cells assessed a... 21602044
Prostaglandin G/H synthase 1 IC50 = 1480.0 nM 5.83 Inhibition of ovine COX1 by EIA 21602044
Prostaglandin G/H synthase 2 IC50 = 1500.0 nM 5.82 Inhibition of sheep COX2 by spectrophotometry 20804197
Prostaglandin G/H synthase 1 IC50 = 2260.0 nM 5.65 In vitro inhibitory concentration against ram seminal vesicle prostaglandin G/H ... 15013005
Prostaglandin G/H synthase 2 IC50 = 2460.0 nM 5.61 Inhibition of human recombinant COX-2 assessed as reduction in PGE2 level using ... 32738413
Prostaglandin G/H synthase 1 IC50 = 2600.0 nM 5.58 Inhibition of COX1 18457385
Prostaglandin G/H synthase 1 IC50 = 3200.0 nM 5.5 Inhibition of sheep COX1 by spectrophotometry 20804197
Prostaglandin G/H synthase 1 IC50 = 4500.0 nM 5.35 Inhibition of ovine COX-1 assessed as reduction in PGE2 level using 10 uM arachi... 32738413
Prostaglandin G/H synthase 1 IC50 = 4960.0 nM 5.3 Competitive inhibition of ovine COX-1 assessed as reduction in PGE2 level using ... 32738413
Prostaglandin G/H synthase 1 IC50 = 16150.0 nM 4.79 Competitive inhibition of ovine COX-1 assessed as reduction in PGE2 level using ... 32738413
Aldo-keto reductase family 1 member C3 IC50 = 32700.0 nM 4.49 Inhibition of human recombinant N-terminal His6-tagged AKR1C3 expressed in Esche... 22877157
Aldo-keto reductase family 1 member C2 IC50 = 42400.0 nM 4.37 Inhibition of human recombinant N-terminal His6-tagged AKR1C2 expressed in Esche... 22877157

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 252
21602044 10.1016/j.bmcl.2011.04.114 Mus musculus 16
21602044 10.1016/j.bmcl.2011.04.114 Nucleic Acid 16
21602044 10.1016/j.bmcl.2011.04.114 Plasma 16
21602044 10.1016/j.bmcl.2011.04.114 Brain 13
- 10.1007/s00044-011-9866-z No relevant target 6
21602044 10.1016/j.bmcl.2011.04.114 Rattus norvegicus 4
32738413 10.1016/j.ejmech.2020.112620 Prostaglandin G/H synthase 1 4
28949138 10.1021/acs.jmedchem.7b01072 Acid-sensing ion channel 1 3
17481895 10.1016/j.bmcl.2007.04.034 Rattus norvegicus 3
17110105 10.1016/j.bmcl.2006.10.087 Prostaglandin G/H synthase 1 2
21602044 10.1016/j.bmcl.2011.04.114 Prostaglandin G/H synthase 1 2
20804197 10.1021/jm100398z Rattus norvegicus 2
28949138 10.1021/acs.jmedchem.7b01072 Acid-sensing ion channel 3 2
16872141 10.1021/np0601556 No relevant target 2
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
15974585 10.1021/jm049082i Interleukin-8 receptors, CXCR1/CXCR2 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2

Data from ChEMBL 36 via Core Engine