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Compound Detail

CHEMBL416146

ETORICOXIB
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(-c2ncc(Cl)cc2-c2ccc(S(C)(=O)=O)cc2)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL416146
Name ETORICOXIB
Phase Approved
Structure Type MOL
InChI Key MNJVRJDLRVPLFE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Arcoxia Etoricoxib L-791456 MK-0663
8
Targets
27
Activities
2
Assay Types
18
PK Parameters
20
Publications
4
Known Names
15
Indications
1
Mechanisms

Molecular Properties

358.9
MW (Da)
4.18
ALogP
4
HBA
0
HBD
59.9
PSA (Ų)
0.70
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Unknown
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -coxib
USAN Year 2000

Extended Properties

Molecular Formula C18H15ClN2O2S
MW 358.85
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -1.31

Mechanism of Action

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

Indications

Rheumatic Diseases Arthritis, Rheumatoid Dysmenorrhea Low Back Pain Osteoarthritis Osteoarthritis, Knee Pain Spondylitis, Ankylosing Toothache Wounds and Injuries Bone Neoplasms HIV Infections Prostatic Neoplasms, Castration-Resistant Melanoma Tuberculosis

ATC Classification

M01AH05
etoricoxib
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Activity Summary

IC50 26 meas. best 7.16
Ki 1 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 7.16 6.325 70.0 16
Prostaglandin G/H synthase 2
CHEMBL230
 Ki 7.16 7.16 69.0 1
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 6.64 6.64 230.0 1
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 6.28 6.28 530.0 1
Unchecked
CHEMBL612545
 IC50 5.96 5.96 1100.0 1
Blood
CHEMBL613416
 IC50 5.96 5.96 1100.0 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 4.92 4.3167 12000.0 3
Bile salt export pump
CHEMBL6020
 IC50 4.35 4.31 45000.0 2
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.28 4.28 53000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1656.0 ng.hr.mL-1 Rattus norvegicus
CL 0.79 mL.min-1.kg-1 Homo sapiens
CL 41.3 mL.min-1.kg-1 Mus musculus
Cmax 30000.0 nM Rattus norvegicus
Cmax 1189.91 nM Rattus norvegicus
Fu 0.081 - Homo sapiens
Fu 0.114 - Homo sapiens
MRT 32.0 hr Homo sapiens
T1/2 26.0 hr Homo sapiens
T1/2 3.067 hr Homo sapiens
T1/2 0.8967 hr Mus musculus
T1/2 6.183 hr Homo sapiens
T1/2 0.4867 hr Mus musculus
T1/2 0.78 hr Mus musculus
T1/2 6.1 hr Homo sapiens
T1/2 2.0 hr Rattus norvegicus
Tmax 0.3 hr Rattus norvegicus
Tmax 0.25 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 70.0 nM 7.16 Inhibition of human COX-2 using arachidonic acid as substrate preincubated for 1... 35685617
Prostaglandin G/H synthase 2 Ki = 69.0 nM 7.16 Inhibition of human recombinant COX-2 using arachidonic acid as substrate preinc... 34279934
Prostaglandin G/H synthase 2 IC50 = 81.0 nM 7.09 In vitro inhibition of PGE-2 produced by arachidonic acid-stimulated CHO cells s... 9873621
Prostaglandin G/H synthase 2 IC50 = 81.0 nM 7.09 Inhibition of human COX-2 transfected in CHO cells using arachidonic acid as sub... 30396033
Prostaglandin G/H synthase 2 IC50 = 230.0 nM 6.64 Inhibition of ovine COX2 using arachidonic acid as substrate preincubated for 10... 30996860
Prostaglandin G/H synthase 2 IC50 = 347.0 nM 6.46 Inhibition of human cyclooxygenase-2 expressed in COS cells 15454242
Prostaglandin G/H synthase 2 IC50 = 347.0 nM 6.46 Inhibition of human COX2 expressed in african green monkey COS cells assessed as... 19520573
Prostaglandin G/H synthase 2 IC50 = 430.0 nM 6.37 Inhibition of human recombinant COX-2 assessed as reduction in peroxidase activi... 34279934
Mitogen-activated protein kinase 14 IC50 = 530.0 nM 6.28 Inhibitory concentration against p38 alpha MAP kinase calculated by CoMFA model;... 15990304
Prostaglandin G/H synthase 2 IC50 = 554.0 nM 6.26 Inhibition of COX2 in human whole blood assessed as inhibition of lipopolysaccha... 19520573
Prostaglandin G/H synthase 2 IC50 = 560.0 nM 6.25 Inhibition of COX2 (unknown origin) expressed in HEK293 TRex cells assessed as r... 34279934
Prostaglandin G/H synthase 2 IC50 = 611.0 nM 6.21 Inhibition of COX2 in human whole blood assessed as reduction in LPS stimulated ... 34279934
Prostaglandin G/H synthase 2 IC50 = 810.0 nM 6.09 Inhibition of COX2 in human whole blood 16616494
Prostaglandin G/H synthase 2 IC50 = 810.0 nM 6.09 Inhibition of COX2 in human whole blood 16647258
Prostaglandin G/H synthase 2 IC50 = 810.0 nM 6.09 Inhibition concentration against cyclooxygenase-2 (COX-2) in human whole blood 15239665
Prostaglandin G/H synthase 2 IC50 = 1100.0 nM 5.96 Inhibition of Prostaglandin G/H synthase 2 was measured by the inhibition of PGE... 9873621
Prostaglandin G/H synthase 2 IC50 = 1100.0 nM 5.96 In vitro inhibition of Prostaglandin G/H synthase 2 in human whole blood assay 11327589
Blood IC50 = 1100.0 nM 5.96 Inhibition of LPS-stimulated PGE2 production in human whole blood 18029174
Unchecked IC50 = 1100.0 nM 5.96 Inhibition of mPGES1 mediated PGE2 production in LPS stimulated human whole bloo... 20965723
Prostaglandin G/H synthase 2 IC50 = 1100.0 nM 5.96 Inhibition of human recombinant COX2 using arachidonic acid as substrate preincu... 29655084

Literature References

PubMed DOI Target Context # Activities
34279934 10.1021/acs.jmedchem.1c00890 ADMET 15
30996860 10.1039/C8MD00457A Erythrocyte 8
29655084 10.1016/j.ejmech.2018.04.007 Mus musculus 6
16616494 10.1016/j.bmcl.2006.03.052 Rattus norvegicus 5
34279934 10.1021/acs.jmedchem.1c00890 Prostaglandin G/H synthase 2 5
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
34279934 10.1021/acs.jmedchem.1c00890 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
9873621 10.1016/s0960-894x(98)00499-5 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
15239665 10.1021/jm049882t Rattus norvegicus 3
34279934 10.1021/acs.jmedchem.1c00890 Prostaglandin G/H synthase 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
30996860 10.1039/C8MD00457A Rattus norvegicus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine