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Compound Detail

CHEMBL118

CELECOXIB
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(-c2cc(C(F)(F)F)nn2-c2ccc(S(N)(=O)=O)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL118
Name CELECOXIB
Phase Approved
Structure Type MOL
InChI Key RZEKVGVHFLEQIL-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Celebra Celebrex Celecoxib Celecoxib component of consensi Celecoxib component of seglentis DFN-15 DFN15 Elyxyb NSC-719627 NSC-758624 Onsenal SC-58635
101
Targets
955
Activities
4
Assay Types
30
PK Parameters
20
Publications
12
Known Names
20
Indications
1
Mechanisms

Molecular Properties

381.4
MW (Da)
3.51
ALogP
4
HBA
1
HBD
78.0
PSA (Ų)
0.75
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Stem -coxib
USAN Year 1998

Extended Properties

Molecular Formula C17H14F3N3O2S
MW 381.38
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -1.57

Mechanism of Action

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

Indications

Acute Pain Adenomatous Polyposis Coli Adenomatous Polyposis Coli Adenomatous Polyposis Coli Arthritis, Juvenile Arthritis, Rheumatoid Dysmenorrhea Hemorrhage Migraine Disorders Neoplasms Neoplasms Osteoarthritis Pain Peptic Ulcer Peptic Ulcer Rheumatic Diseases Spondylitis Spondylitis, Ankylosing Stroke Adenoma

ATC Classification

L01XX33
celecoxib
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS
M01AH01
celecoxib
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

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

Activity Summary

IC50 745 meas. best 9.29
Ki 204 meas. best 9.33
EC50 5 meas. best 8.94
Kd 1 meas. best 7.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 Ki 9.33 9.33 0.5 1
Prostaglandin G/H synthase 2
CHEMBL4321
 IC50 9.29 7.2112 0.5 17
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 9.28 6.934 0.5 222
Prostaglandin G/H synthase 1
CHEMBL2649
 IC50 9.15 5.8563 0.7 8
Unchecked
CHEMBL612545
 EC50 8.94 8.94 1.1 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 8.43 4.8853 3.7 111
Carbonate dehydratase
CHEMBL3745586
 Ki 8.16 8.16 6.9 1
Unchecked
CHEMBL612545
 Ki 8.16 6.1058 6.9 43
Unchecked
CHEMBL612545
 IC50 8.1 4.9343 7.9 21
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 7.89 5.1269 13.0 91
Carbonic anhydrase 9
CHEMBL3594
 Ki 7.83 6.7767 14.8 3
Carbonic anhydrase 2
CHEMBL205
 Kd 7.8 7.8 15.8 1
Carbonic anhydrase 9
CHEMBL3594
 IC50 7.8 7.8 16.0 2
Carbonic anhydrase 12
CHEMBL3242
 Ki 7.75 7.75 18.0 7
Carbonic anhydrase 2
CHEMBL205
 IC50 7.68 7.445 21.0 4
Alpha carbonic anhydrase
CHEMBL1075028
 Ki 7.47 7.47 34.2 2
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 7.4 6.8415 40.0 73
Cytochrome c oxidase subunit 2
CHEMBL1250404
 IC50 7.37 7.11 42.6 4
Carbonic anhydrase 15
CHEMBL5973
 Ki 7.35 7.35 45.0 2
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL2903
 IC50 7.31 7.31 49.0 1
Prostaglandin G/H synthase 2
CHEMBL3331
 IC50 7.24 7.23 57.0 2
Prostaglandin G/H synthase 2
CHEMBL2977
 IC50 7.15 6.6533 71.0 3
Carbonic anhydrase 2
CHEMBL205
 Ki 7.12 6.06 76.8 3
Cyclooxygenase
CHEMBL2094253
 IC50 7.05 7.05 89.0 1
Carbonic anhydrase 6
CHEMBL3025
 Ki 7.03 7.03 94.0 3
Carbonic anhydrase 5B, mitochondrial
CHEMBL3969
 Ki 7.03 7.03 93.0 2
Carbonic anhydrase 13
CHEMBL3912
 Ki 7.01 7.01 98.0 2
RAW264.7
CHEMBL612557
 IC50 7.0 5.1239 100.0 23
Carbonic anhydrase
CHEMBL5931
 Ki 6.97 6.97 108.0 1
Carbonic anhydrase
CHEMBL6185
 Ki 6.94 6.94 116.0 1
Cyclooxygenase
CHEMBL2095157
 IC50 6.88 6.88 132.0 1
Carbonic anhydrase
CHEMBL3932
 Ki 6.85 6.425 140.0 2
Homo sapiens
CHEMBL372
 IC50 6.79 5.732 164.0 5
AGAP002992-PA
CHEMBL3399914
 Ki 6.76 6.76 173.0 1
Delta carbonic anhydrase
CHEMBL3097982
 Ki 6.58 6.58 265.0 1
Cytochrome c oxidase subunit 2
CHEMBL6174
 IC50 6.55 6.45 280.0 3
Carbonic anhydrase 4
CHEMBL281
 IC50 6.54 6.54 290.0 2
Carbonic anhydrase 4
CHEMBL281
 Ki 6.54 6.54 290.0 2
Carbonic anhydrase 4
CHEMBL3729
 Ki 6.54 6.252 290.0 5
MC9
CHEMBL614867
 IC50 6.52 6.46 300.0 2
HepG2
CHEMBL395
 IC50 6.44 5.1843 360.0 7
Prostaglandin E synthase
CHEMBL5658
 IC50 6.37 5.9025 425.0 4
Histone deacetylase 6
CHEMBL1865
 IC50 6.19 6.19 643.0 1
Carbonic anhydrase
CHEMBL1649055
 Ki 6.16 6.16 690.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 6.16 6.16 692.0 1
Carbonic anhydrase 14
CHEMBL3510
 Ki 6.16 6.16 689.0 2
HT-29
CHEMBL384
 IC50 6.16 5.0814 700.0 7
Carbonic anhydrase 2
CHEMBL6068
 Ki 6.15 6.15 713.0 2
Astrosclerin-3
CHEMBL1944499
 Ki 6.13 6.13 732.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.12 5.3267 750.0 9

Pharmacokinetic Data

Parameter Value Units Species
AUC 3100.0 ng.hr.mL-1 Canis lupus familiaris
AUC 23160.0 ng.hr.mL-1 Rattus norvegicus
AUC 6600.0 ng.hr.mL-1 Mus musculus
CL 25.7 uL.min-1.(10^6cells)-1 Homo sapiens
CL - - Homo sapiens
CL - - Homo sapiens
CL 10.5 mL.min-1.kg-1 Mus musculus
Cmax 1415.91 nM Canis lupus familiaris
Cmax 6476.48 nM Rattus norvegicus
Cmax 3146.47 nM Mus musculus
Fu 0.003 - Homo sapiens
Fu 0.0031 - Homo sapiens
T1/2 3.3 hr Canis lupus familiaris
T1/2 3.5 hr Rattus norvegicus
T1/2 3.5 hr Rattus norvegicus
T1/2 11.2 hr Homo sapiens
T1/2 3.5 hr Rattus norvegicus
T1/2 3.5 hr Rattus norvegicus
T1/2 1.12 hr Homo sapiens
T1/2 0.9883 hr Mus musculus
T1/2 0.9567 hr Homo sapiens
T1/2 0.5517 hr Mus musculus
T1/2 1.27 hr Mus musculus
T1/2 0.71 hr Homo sapiens
T1/2 5.2 hr Mus musculus
T1/2 3.5 hr Rattus norvegicus
T1/2 12.0 hr Homo sapiens
Tmax - hr Canis lupus familiaris
Tmax 3.25 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 Ki = 0.47 nM 9.33 Inhibition of human recombinant COX-2 using arachidonic acid as substrate preinc... 34279934
Prostaglandin G/H synthase 2 IC50 = 0.51 nM 9.29 Inhibition of LPS-induced COX2 activity in C57BL/6J mouse peritoneal macrophages... 17125227
Prostaglandin G/H synthase 2 IC50 = 0.52 nM 9.28 Inhibition of COX2 17714833
Prostaglandin G/H synthase 2 IC50 = 0.52 nM 9.28 Inhibition of COX2 17714833
Prostaglandin G/H synthase 1 IC50 = 0.7 nM 9.15 Tested for inhibition against Prostaglandin G/H synthase 2 from mouse resident m... 11101350
Unchecked EC50 = 1.15 nM 8.94 Inhibition of IL-1beta-induced PGE2 production in human HCA-7 cells after 72 hrs... 22516282
Prostaglandin G/H synthase 2 IC50 = 2.0 nM 8.7 Inhibition of PGE-2 production in CHO cells expressing human COX-2. 10576685
Prostaglandin G/H synthase 2 IC50 = 2.0 nM 8.7 In vitro inhibitory potency against human COX-2 in stably transfected chinese ha... 10576684
Prostaglandin G/H synthase 2 IC50 = 2.0 nM 8.7 In vitro potency against human Prostaglandin G/H synthase 2 in transfected CHO c... 10197970
Prostaglandin G/H synthase 2 IC50 = 2.0 nM 8.7 Inhibitory of human Prostaglandin G/H synthase 2 expressed in CHO cells. 12643942
Prostaglandin G/H synthase 2 IC50 = 2.2 nM 8.66 Inhibition of COX2 16806914
Prostaglandin G/H synthase 2 IC50 = 3.2 nM 8.49 In vivo inhibition of COX2 in po dosed C57BL/6J mouse model of spontaneous GI-tr... 34279934
Prostaglandin G/H synthase 2 IC50 = 3.2 nM 8.49 In vivo inhibition of COX2 in po dosed C57BL/6J mouse model of spontaneous GI-tr... 34279934
Prostaglandin G/H synthase 1 IC50 = 3.7 nM 8.43 Inhibition of COX1 16806914
Prostaglandin G/H synthase 2 IC50 = 4.8 nM 8.32 Inhibition of COX2 (unknown origin) using arachidonic acid as substrate pretreat... 28427813
Prostaglandin G/H synthase 2 IC50 = 6.0 nM 8.22 Inhibition of human recombinant COX-2 using arachidonic acid as substrate by flu... 34245948
Prostaglandin G/H synthase 2 IC50 = 6.0 nM 8.22 Inhibitory concentration against COX-2 upon incubation for 15 minutes at 37 degr... 16250658
Prostaglandin G/H synthase 2 IC50 = 6.8 nM 8.17 Inhibitory concentration against COX-2; (valus obtained by Kato et al.) 16250658
Unchecked Ki = 6.9 nM 8.16 Inhibition of Sulfurihydrogenibium yellowstonense YO3AOP1 recombinant carbonic a... 22883029
Carbonate dehydratase Ki = 6.9 nM 8.16 Inhibition of recombinant Sulfurihydrogenibium yellowstonense YO3AOP1 carbonic a... 26691758

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 576
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 46
31445233 10.1016/j.ejmech.2019.111601 Rattus norvegicus 29
18072726 10.1021/jm070821f Rattus norvegicus 27
20937780 10.1128/aac.00735-10 Unchecked 24
34279934 10.1021/acs.jmedchem.1c00890 ADMET 16
31803395 10.1039/C9MD00228F ADMET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
35685617 10.1039/d1md00280e Prostaglandin G/H synthase 2 11
33347967 10.1016/j.bmcl.2020.127754 Rattus norvegicus 10
24836072 10.1016/j.ejmech.2014.05.012 Rattus norvegicus 9
15566290 10.1021/jm0407761 LNCaP 9
19398640 10.1128/aac.00048-09 NON-PROTEIN TARGET 9
30904755 10.1016/j.ejmech.2019.03.036 Rattus norvegicus 9
30928709 10.1016/j.ejmech.2019.03.042 Rattus norvegicus 9
20598893 10.1016/j.bmc.2010.06.002 Mus musculus 9
20609589 10.1016/j.bmc.2010.06.018 Rattus norvegicus 9
37544187 10.1016/j.ejmech.2023.115697 Mus musculus 9

Data from ChEMBL 36 via Core Engine