ROFECOXIB

Search structure
Trade Names:
Synonyms:
Status: Approved (1999) Withdrawn (2004)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: M01AH02
UNII: 0QTW8Z7MCR

Structure
InChI Key RZJQGNCSTQAWON-UHFFFAOYSA-N
Smile CS(=O)(=O)c1ccc(C2=C(c3ccccc3)C(=O)OC2)cc1
InChI
InChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C17H14O4S
Molecular Weight 314.36
AlogP 2.56
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 60.44
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 22.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cyclooxygenase-2 inhibitor FDA
Primary Target
COX-2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 71
Enzyme Oxidoreductase
- 1-26000 - - 26-100
Enzyme
- 1-26000 - - 26-100
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- - - - -10-28
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 134
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 95360 - - -
Transporter Primary active transporter Oxidoreduction-driven transporters
- 20-3000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Osteoarthritis 3 D010003 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Joint Diseases 3 D007592 ClinicalTrials
Adenoma 3 D000236 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Osteoarthritis, Knee 3 D020370 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Glioma 1 D005910 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Diarrhoea 10.6
Gastrointestinal disorders Epigastric discomfort 9.2
Infections and infestations Upper respiratory tract infection 8.5
Vascular disorders Hypertension 8.2
Infections and infestations Upper respiratory tract infection 8.2
Nervous system disorders Headache 8.0
Infections and infestations Upper respiratory tract infection
Nervous system disorders Headache
Nervous system disorders Headache 7.5
Gastrointestinal disorders Nausea 7.4
Gastrointestinal disorders Diarrhoea 7.1
Gastrointestinal disorders Nausea 7.1
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 6.5
Cardiac disorders Oedema peripheral 6.3
Nervous system disorders Headache 6.1
Gastrointestinal disorders Abdominal pain 5.8
Gastrointestinal disorders Gastrointestinal pain 5.8
Infections and infestations Upper respiratory tract infection 5.8
Gastrointestinal disorders Epigastric discomfort 5.4
Gastrointestinal disorders Dyspepsia 5.2
Gastrointestinal disorders Nausea 5.2
Gastrointestinal disorders Dyspepsia 4.7
Nervous system disorders Headache 4.7
Gastrointestinal disorders Abdominal pain 4.6
Gastrointestinal disorders Dyspepsia 4.6
Gastrointestinal disorders Gastrointestinal pain 4.6
Gastrointestinal disorders Dyspepsia 4.2
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Dyspepsia 4.0
Gastrointestinal disorders Epigastric discomfort 3.8
Cardiac disorders Oedema peripheral 3.8
Cardiac disorders Oedema peripheral 3.7
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 3.6
Infections and infestations Urinary tract infection 3.6
Gastrointestinal disorders Dyspepsia 3.5
Vascular disorders Hypertension 3.5
Gastrointestinal disorders Abdominal pain 3.4
Cardiac disorders Dizziness 3.4
Gastrointestinal disorders Gastrointestinal pain 3.4
Cardiac disorders Oedema peripheral 3.4
Infections and infestations Bronchitis 3.2
Infections and infestations Influenza 3.2
Infections and infestations Influenza
Infections and infestations Influenza 3.1
Cardiac disorders Dizziness 3.0
Vascular disorders Hypertension 3.0
Infections and infestations Influenza 2.9
Gastrointestinal disorders Nausea
Musculoskeletal and connective tissue disorders Back pain 2.8
Gastrointestinal disorders Epigastric discomfort
Gastrointestinal disorders Epigastric discomfort 2.8
Infections and infestations Urinary tract infection 2.8
Cardiac disorders Dizziness 2.7
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 2.7
Infections and infestations Sinusitis 2.7
Infections and infestations Urinary tract infection
Infections and infestations Urinary tract infection 2.7
General disorders and administration site conditions Asthenia 2.6
General disorders and administration site conditions Fatigue 2.6
Musculoskeletal and connective tissue disorders Back pain 2.5
Infections and infestations Urinary tract infection 2.5
Infections and infestations Sinusitis 2.4
General disorders and administration site conditions Asthenia 2.2
Cardiac disorders Dizziness
Cardiac disorders Dizziness 2.2
General disorders and administration site conditions Fatigue 2.2
General disorders and administration site conditions Asthenia 2.0
Infections and infestations Bronchitis 2.0
General disorders and administration site conditions Fatigue 2.0
Infections and infestations Sinusitis
Musculoskeletal and connective tissue disorders Back pain
Infections and infestations Sinusitis 1.8
Vascular disorders Hypertension 1.6
Infections and infestations Influenza 1.5
Musculoskeletal and connective tissue disorders Back pain 1.4
Infections and infestations Bronchitis 1.4
Vascular disorders Hypertension
Cardiac disorders Oedema peripheral
Cardiac disorders Oedema peripheral 1.1
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 1.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 1.0
Infections and infestations Bronchitis
Infections and infestations Bronchitis 0.8

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
14.77
Cardiac disorders
13.56
Nervous system disorders
12.59
Gastrointestinal disorders
11.62
Psychiatric disorders
10.17
General disorders and administration site conditions
7.26
Respiratory, thoracic and mediastinal disorders
5.81
Metabolism and nutrition disorders
4.84
Musculoskeletal and connective tissue disorders
4.36
Investigations
2.42
Skin and subcutaneous tissue disorders
2.42

Cross References

Resources Reference
CAS NUMBER 162011-90-7
ChEBI 8887
ChEMBL CHEMBL122
DrugBank DB00533
DrugCentral 2397
EPA CompTox DTXSID2023567
FDA SRS 0QTW8Z7MCR
Guide to Pharmacology 2893
KEGG C07590
PDB RCX
PharmGKB PA451268
PubChem 5090
SureChEMBL SCHEMBL3050
ZINC ZINC000000007455
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