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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL122
CHEMBL122
Compound Name ROFECOXIB
ChEMBL Synonyms MK-966 | Vioxx | ROFECOXIB | MK-0966
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names Vioxx
Molecular Formula C17H14O4S

Additional synonyms for CHEMBL122 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CS(=O)(=O)c1ccc(cc1)C2=C(C(=O)OC2)c3ccccc3
Standard InChI InChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17 ...
Download InChI
Standard InChI Key RZJQGNCSTQAWON-UHFFFAOYSA-N

Alternate Forms of Compound in ChEMBL


CHEMBL122

Molecule Features

CHEMBL122 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 2004
Country United States
Reason Risk for heart attack and stroke

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cyclooxygenase-2 inhibitor Cyclooxygenase-2 FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication
ADENOMATOUS POLYPOSIS COLID011125EFO:0000662POLYP2
BARRETT ESOPHAGUSD001471EFO:0000280BARRETT'S ESOPHAGUS4
OSTEOARTHRITISD010003EFO:0002506OSTEOARTHRITIS3
OSTEOARTHRITIS, KNEED020370EFO:0004616OSTEOARTHRITIS, KNEE3
PAIND010146EFO:0003843PAIN4
RHEUMATIC DISEASESD012216EFO:0005755RHEUMATIC DISEASE4

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL122. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL230 Cyclooxygenase-2 Homo sapiens 1.000
CHEMBL4102 Cyclooxygenase-2 Ovis aries 1.000
CHEMBL221 Cyclooxygenase-1 Homo sapiens 1.000
CHEMBL2949 Cyclooxygenase-1 Ovis aries 1.000
CHEMBL4321 Cyclooxygenase-2 Mus musculus 1.000
CHEMBL2035 Muscarinic acetylcholine receptor M5 Homo sapiens 0.280



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4102 Cyclooxygenase-2 Ovis aries 1.000
CHEMBL230 Cyclooxygenase-2 Homo sapiens 1.000
CHEMBL2949 Cyclooxygenase-1 Ovis aries 1.000
CHEMBL221 Cyclooxygenase-1 Homo sapiens 1.000
CHEMBL4321 Cyclooxygenase-2 Mus musculus 1.000
CHEMBL2649 Cyclooxygenase-1 Mus musculus 0.499

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
314.4 314.0613 2.87 3 68.81 -


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 0 0 4 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- - -.34 -.34 2 22 0.82

Structural Alerts

There are 3 structural alerts for CHEMBL122. To view alerts please click here.

Compound Cross References

ATC M - MUSCULO-SKELETAL SYSTEM
M01 - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01A - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01AH - Coxibs
M01AH02 - rofecoxib

ChemSpider ChemSpider:RZJQGNCSTQAWON-UHFFFAOYSA-N
PubChem SID: 144204983 SID: 174007305 SID: 26748942 SID: 49665949 SID: 535364
Wikipedia Rofecoxib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL122



ACToR 162011-90-7
Atlas rofecoxib
BindingDB 22369
ChEBI 8887
DrugBank DB00533
eMolecules 877485
EPA CompTox Dashboard DTXSID2023567
FDA SRS 0QTW8Z7MCR
Guide to Pharmacology 2893
IBM Patent System 36EB78C6AA952065C4F2A7E1A37AE41E
KEGG Ligand C07590
LINCS LSM-2482
Mcule MCULE-4806636118
MolPort MolPort-006-817-786 MolPort-000-883-878
NIH Clinical Collection SAM001246617
Nikkaji J1.041.252H
PDBe RCX
PharmGKB PA451268
PubChem 5090
PubChem: Drugs of the Future 12014954
PubChem: Thomson Pharma 14752370
Selleck rofecoxib-vioxx
SureChEMBL SCHEMBL3050
ZINC ZINC00007455

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/RZJQGNCSTQAWON-UHFFFAOYSA-N spacer
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