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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL865
CHEMBL865
Compound Name VALDECOXIB
ChEMBL Synonyms SC-65872 | BEXTRA | VALDECOXIB
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names BEXTRA
Molecular Formula C16H14N2O3S

Additional synonyms for CHEMBL865 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1onc(c2ccccc2)c1c3ccc(cc3)S(=O)(=O)N
Standard InChI InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20) ...
Download InChI
Standard InChI Key LNPDTQAFDNKSHK-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL865

Molecule Features

CHEMBL865 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First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Withdrawn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 DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
PANCREATITISD010195EFO:0000278PANCREATITIS2ClinicalTrials
OSTEOARTHRITISD010003EFO:0002506OSTEOARTHRITIS3ClinicalTrials
RHEUMATIC DISEASESD012216EFO:0005755RHEUMATIC DISEASE4ATC
PAIND010146EFO:0003843PAIN3ClinicalTrials

Clinical Data

ClinicalTrials.gov VALDECOXIB
The Cochrane Collaboration VALDECOXIB

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 CHEMBL865. 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
CHEMBL221 Cyclooxygenase-1 Homo sapiens 1.000
CHEMBL230 Cyclooxygenase-2 Homo sapiens 1.000
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 1.000
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 1.000
CHEMBL4321 Cyclooxygenase-2 Mus musculus 1.000
CHEMBL205 Carbonic anhydrase II Homo sapiens 1.000
CHEMBL261 Carbonic anhydrase I Homo sapiens 1.000
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.999
CHEMBL4102 Cyclooxygenase-2 Ovis aries 0.996
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.965
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.921
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.700
CHEMBL1163125 Bromodomain-containing protein 4 Homo sapiens 0.653
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.593
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.574
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.274
CHEMBL3912 Carbonic anhydrase XIII Homo sapiens 0.236
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.211



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL221 Cyclooxygenase-1 Homo sapiens 1.000
CHEMBL230 Cyclooxygenase-2 Homo sapiens 1.000
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 1.000
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 1.000
CHEMBL205 Carbonic anhydrase II Homo sapiens 1.000
CHEMBL4321 Cyclooxygenase-2 Mus musculus 1.000
CHEMBL261 Carbonic anhydrase I Homo sapiens 1.000
CHEMBL4102 Cyclooxygenase-2 Ovis aries 0.999
CHEMBL1163125 Bromodomain-containing protein 4 Homo sapiens 0.998
CHEMBL5767 PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) Mycobacterium tuberculosis 0.997
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.996
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.994
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.994
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.990
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.938
CHEMBL5973 Carbonic anhydrase 15 Mus musculus 0.913
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.837
CHEMBL3912 Carbonic anhydrase XIII Homo sapiens 0.837
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.831
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.678

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
314.4 314.0725 2.6 3 94.57 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 1 0 5 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.83 - 3.57 3.56 3 22 0.81

Structural Alerts

There are no structural alerts for CHEMBL865

Compound Cross References

ATC M - MUSCULO-SKELETAL SYSTEM
M01 - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01A - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01AH - Coxibs
M01AH03 - valdecoxib

ChemSpider ChemSpider:LNPDTQAFDNKSHK-UHFFFAOYSA-N
PubChem SID: 144204991 SID: 170465163 SID: 26748964 SID: 49665731
Wikipedia Valdecoxib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL865



ACToR 181695-72-7
BindingDB 13063
ChEBI 63634
DrugBank DB00580
DrugCentral 2799
eMolecules 877479
EPA CompTox Dashboard DTXSID6044226
FDA SRS 2919279Q3W
Guide to Pharmacology 2894
Human Metabolome Database HMDB05033
IBM Patent System 2B8E65AD6AAC448B0C7672B494F82F98
LINCS LSM-5305
MolPort MolPort-000-883-874
NIH Clinical Collection SAM001246603
Nikkaji J1.302.764A
NMRShiftDB 20082
PDBe COX
PharmGKB PA10226
PubChem 119607
PubChem: Drugs of the Future 12015079
PubChem: Thomson Pharma 14850214
Selleck valdecoxib
SureChEMBL SCHEMBL3356
ZINC ZINC000000006694

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