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Compound Detail

CHEMBL122

ROFECOXIB
💊 Approved Drug
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💊 Approved Drug
CS(=O)(=O)c1ccc(C2=C(c3ccccc3)C(=O)OC2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL122
Name ROFECOXIB
Phase Approved
Structure Type MOL
InChI Key RZJQGNCSTQAWON-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

M01AH02 MK-0966 MK-966 MK0966 NSC-720256 NSC-758705 Rofecoxib TRM-201 TRM201 Vioxx
12
Targets
131
Activities
3
Assay Types
9
PK Parameters
20
Publications
10
Known Names
13
Indications
1
Mechanisms

Molecular Properties

314.4
MW (Da)
2.56
ALogP
4
HBA
0
HBD
60.4
PSA (Ų)
0.82
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Withdrawn
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product
USAN Stem -coxib
USAN Year 1998

Extended Properties

Molecular Formula C17H14O4S
MW 314.36
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.07

Mechanism of Action

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

Indications

Rheumatic Diseases Adenoma Colorectal Neoplasms Joint Diseases Osteoarthritis Osteoarthritis, Knee Pain Prostatic Neoplasms, Castration-Resistant Stomach Neoplasms Alzheimer Disease Carcinoma, Non-Small-Cell Lung Brain Neoplasms Paraganglioma

ATC Classification

M01AH02
rofecoxib
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Withdrawn
cardiotoxicity
Risk for heart attack and stroke
Country: Worldwide   Year: 2004
Withdrawn
cardiotoxicity
Risk for heart attack and stroke
Country: Worldwide   Year: 2004
Withdrawn
cardiotoxicity
Increased risk in cardiovascular events such as heart attack and strokes especially when used for long duration.
Country: Worldwide   Year: 2004
Withdrawn
cardiotoxicity
Increased risk of cardiovascular side effects
Country: Worldwide   Year: 2004
Withdrawn
cardiotoxicity
Increased risk in cardiovascular events such as heart attack and strokes especially when used for long duration.
Country: Worldwide   Year: 2004
Withdrawn
cardiotoxicity
Increased risk of serious cardiovascular events, such as heart attacks and strokes
Country: Worldwide   Year: 2004
Withdrawn
neurotoxicity
Risk for heart attack and stroke
Country: Worldwide   Year: 2004
Withdrawn
cardiotoxicity
Increased risk of serious cardiovascular events, such as heart attacks and strokes
Country: Worldwide   Year: 2004
Withdrawn
neurotoxicity
Increased risk of serious cardiovascular events, such as heart attacks and strokes
Country: Worldwide   Year: 2004
Withdrawn
neurotoxicity
Increased risk in cardiovascular events such as heart attack and strokes especially when used for long duration.
Country: Worldwide   Year: 2004

Activity Summary

IC50 128 meas. best 9.0
EC50 2 meas.
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 9.0 6.641 1.0 62
Prostaglandin G/H synthase 2
CHEMBL4321
 IC50 7.92 7.57 12.0 2
Cytochrome c oxidase subunit 2
CHEMBL6174
 IC50 7.7 6.61 20.0 2
Mesenteric artery
CHEMBL4296533
 IC50 7.06 6.42 88.0 2
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 6.52 6.3195 300.0 19
Prostaglandin G/H synthase 2
CHEMBL3331
 IC50 6.37 6.37 430.0 1
Unchecked
CHEMBL612545
 IC50 6.28 6.28 530.0 1
Prostaglandin G/H synthase 2
CHEMBL2977
 IC50 6.12 6.12 760.0 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 5.77 4.8141 1700.0 29
Prostaglandin G/H synthase 1
CHEMBL4042
 IC50 4.94 4.94 11400.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 4.63 4.515 23500.0 2
Bile salt export pump
CHEMBL6020
 IC50 4.02 4.02 95360.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 57880.0 ng.hr.mL-1 Rattus norvegicus
AUC 531.0 ng.hr.mL-1 Rattus norvegicus
Cmax 17845.78 nM Rattus norvegicus
Cmax 753.91 nM Rattus norvegicus
Cmax 7685.46 nM Rattus norvegicus
F 93.0 % Homo sapiens
T1/2 4.18 hr Rattus norvegicus
Tmax 3.0 hr Rattus norvegicus
Tmax 0.4 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 = 1.0 nM 9.0 The compound was evaluated for prostaglandin E2 inhibition using recombinant Pro... 11859001
Prostaglandin G/H synthase 2 IC50 = 12.0 nM 7.92 In vitro inhibitory activity against human Prostaglandin G/H synthase 2 (COX-2) ... 12877584
Prostaglandin G/H synthase 2 IC50 = 12.0 nM 7.92 In vitro inhibitory activity against Prostaglandin G/H synthase 2 in murine J774... 15857149
Prostaglandin G/H synthase 2 IC50 = 15.0 nM 7.82 Inhibitory concentration against COX-2 upon incubation for 15 minutes at 37 degr... 16250658
Prostaglandin G/H synthase 2 IC50 = 20.0 nM 7.7 Inhibition of PGE-2 production in CHO cells expressing human COX-2. 10576685
Prostaglandin G/H synthase 2 IC50 = 20.0 nM 7.7 In vitro potency against human Prostaglandin G/H synthase 2 in transfected CHO c... 10197970
Prostaglandin G/H synthase 2 IC50 = 20.0 nM 7.7 In vitro inhibitory potency against human COX-2 in stably transfected chinese ha... 10576684
Prostaglandin G/H synthase 2 IC50 = 20.0 nM 7.7 Inhibitory of human Prostaglandin G/H synthase 2 expressed in CHO cells. 12643942
Prostaglandin G/H synthase 2 IC50 = 20.0 nM 7.7 In vitro inhibitory activity against human whole cells (CHO) Prostaglandin G/H s... 10406640
Cytochrome c oxidase subunit 2 IC50 = 20.0 nM 7.7 Inhibition of COX2 (unknown origin) 31445233
Prostaglandin G/H synthase 2 IC50 = 25.0 nM 7.6 Inhibitory concentration against COX-2; (valus obtained by Kato et al.) 16250658
Prostaglandin G/H synthase 2 IC50 = 25.0 nM 7.6 Enzyme (COXs) Inhibition Assay: The inhibitory effects of candidate compounds on... -
Prostaglandin G/H synthase 2 IC50 = 27.0 nM 7.57 Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate preincu... 36796297
Prostaglandin G/H synthase 2 IC50 = 32.0 nM 7.5 Inhibition of human cyclooxygenase-2 expressed in COS cells 15454242
Prostaglandin G/H synthase 2 IC50 = 32.0 nM 7.5 Inhibition of human COX2 expressed in african green monkey COS cells assessed as... 19520573
Prostaglandin G/H synthase 2 IC50 = 57.0 nM 7.24 Inhibitory activity against Prostaglandin G/H synthase 2 in human whole blood as... 12639552
Prostaglandin G/H synthase 2 IC50 = 60.0 nM 7.22 Inhibition of mouse COX-2 assessed as inhibition of [14C]arachidonic acid to rad... 25408841
Prostaglandin G/H synthase 2 IC50 = 74.5 nM 7.13 Inhibition of human recombinant COX2 expressed in Sf21 cells assessed as effect ... 19056264
Mesenteric artery IC50 = 88.0 nM 7.06 Inhibition of acetylcholine-induced relaxation in Long Evans rat phenylephrine p... 21641217
Prostaglandin G/H synthase 2 IC50 = 107.0 nM 6.97 Inhibition of human COX2 expressed in baculovirus-infected SF9 cells assessed as... 19520573

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 767
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
19398640 10.1128/aac.00048-09 NON-PROTEIN TARGET 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
32992247 10.1016/j.bmc.2020.115760 Unchecked 8
21752640 10.1016/j.bmcl.2011.06.029 Voltage-gated inwardly rectifying potassium channel KCNH2 6
14640557 10.1021/jm030268b Prostaglandin G/H synthase 2 6
15566290 10.1021/jm0407761 LNCaP 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
12877584 10.1021/jm030765s Rattus norvegicus 6
17467123 10.1016/j.ejmech.2007.02.008 Rattus norvegicus 6
15084117 10.1021/jm030276s Prostaglandin G/H synthase 2 5
21641217 10.1016/j.bmcl.2011.05.017 Mesenteric artery 5
16616494 10.1016/j.bmcl.2006.03.052 Rattus norvegicus 5
12392741 10.1016/s0960-894x(02)00739-4 Rattus norvegicus 4
12954051 10.1021/jm020563g Rattus norvegicus 4
12877584 10.1021/jm030765s Prostaglandin G/H synthase 2 4
31746599 10.1021/acs.jmedchem.9b01304 Mus musculus 4
10406640 10.1016/s0960-894x(99)00288-7 Rattus norvegicus 4

Data from ChEMBL 36 via Core Engine