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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL118
CHEMBL118
Compound Name CELECOXIB
ChEMBL Synonyms ONSENAL | CELECOXIB | SC-58635 | Celebra | CELEBREX
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names Celebra | CELEBREX | CELECOXIB | ONSENAL
Molecular Formula C17H14F3N3O2S

Additional synonyms for CHEMBL118 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1ccc(cc1)c2cc(nn2c3ccc(cc3)S(=O)(=O)N)C(F)(F)F
Standard InChI InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19 ...
Download InChI
Standard InChI Key RZEKVGVHFLEQIL-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • HeCaToS Compounds
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL118

Molecule Features

CHEMBL118 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:Prescription-only

Withdrawal Information

Year 2011
Country European Union
Reason
Class

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
Arthritis, JuvenileD001171EFO:0002609chronic childhood arthritis4ClinicalTrials
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Depression, PostpartumD019052EFO:0007453postpartum depression3ClinicalTrials
InflammationD007249MP:0001845inflammation1ClinicalTrials
Influenza, HumanD007251EFO:0001669influenza infection3ClinicalTrials
NeuralgiaD009437EFO:0005762neuropathic pain2ClinicalTrials
ObesityD009765EFO:0001073obesity0ClinicalTrials
Osteoarthritis, HipD015207EFO:1000786osteoarthritis, hip3ClinicalTrials
Osteoarthritis, KneeD020370EFO:0004616osteoarthritis, knee3ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
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Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma2ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001416cervical adenocarcinoma2ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury3ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease3ClinicalTrials
Macular DegenerationD008268EFO:0001365age-related macular degeneration3ClinicalTrials
Muscular Atrophy, SpinalD0091342ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm3ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
Skin NeoplasmsD012878EFO:0004198skin neoplasm2ClinicalTrials
Temporomandibular Joint DisordersD013705EFO:0005279temporomandibular joint disorder2ClinicalTrials
Amyotrophic Lateral SclerosisD000690EFO:0000253amyotrophic lateral sclerosis2ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
DysmenorrheaD0044124DailyMed
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder1ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
PainD010146EFO:0003843pain4ClinicalTrials
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TonsillitisD0140692ClinicalTrials
Uterine NeoplasmsD014594EFO:0003859uterine neoplasm2ClinicalTrials
AdenomaD000236EFO:0005406colorectal adenoma3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis4ClinicalTrials
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Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma3ClinicalTrials
GoutD006073EFO:0004274gout3ClinicalTrials
Graves OphthalmopathyD049970EFO:1001466Graves ophthalmopathy2ClinicalTrials
HistiocytomaD051642EFO:0005561histiocytoma1ClinicalTrials
LymphangioleiomyomatosisD018192Orphanet:538Lymphangioleiomyomatosis2ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma2ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma1ClinicalTrials
Prostatic HyperplasiaD011470EFO:0000284benign prostatic hyperplasia2ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia2ClinicalTrials
Tobacco Use DisorderD014029EFO:0003768nicotine dependence3ClinicalTrials
TuberculosisD014376Orphanet:3389Tuberculosis1ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
HypertensionD006973EFO:0000537hypertension3ClinicalTrials
Memory DisordersD008569EFO:0001072memory impairment3ClinicalTrials
Neurofibromatosis 1D009456Orphanet:636Neurofibromatosis type 12ClinicalTrials
OsteoarthritisD010003EFO:0002506osteoarthritis4ClinicalTrials
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Ovarian NeoplasmsD010051EFO:0003893ovarian neoplasm2ClinicalTrials
Papillomavirus InfectionsD030361EFO:0001668human papilloma virus infection2ClinicalTrials
ParaproteinemiasD010265EFO:0000203monoclonal gammopathy2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer2ClinicalTrials
Spondylitis, AnkylosingD013167EFO:0003898ankylosing spondylitis4ClinicalTrials
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Bipolar DisorderD001714EFO:0000289bipolar disorder3ClinicalTrials
Colonic NeoplasmsD003110EFO:0004288colonic neoplasm3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
Pre-EclampsiaD011225EFO:0000668preeclampsia2ClinicalTrials
StomatitisD013280EFO:1001904oral mucositis2ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma2ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma2ClinicalTrials
Adenomatous Polyposis ColiD011125Orphanet:733Familial adenomatous polyposis4ClinicalTrials
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Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
Colonic NeoplasmsD003110EFO:1001950colon carcinoma3ClinicalTrials
GliomaD005910EFO:0005543glioma2ClinicalTrials
Hypotension, OrthostaticD007024EFO:0005252orthostatic hypotension1ClinicalTrials
Mouth NeoplasmsD009062EFO:0003868mouth neoplasm1ClinicalTrials
Rheumatic DiseasesD012216EFO:0005755rheumatic disease4ATC

Clinical Data

ClinicalTrials.gov CELECOXIB
The Cochrane Collaboration CELECOXIB

Metabolites for CHEMBL118

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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 CHEMBL118. 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
CHEMBL4033 Cyclooxygenase-2 Canis lupus familiaris 1.000
CHEMBL221 Cyclooxygenase-1 Homo sapiens 1.000
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 1.000
CHEMBL4321 Cyclooxygenase-2 Mus musculus 1.000
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 1.000
CHEMBL205 Carbonic anhydrase II Homo sapiens 1.000
CHEMBL261 Carbonic anhydrase I Homo sapiens 1.000
CHEMBL4102 Cyclooxygenase-2 Ovis aries 1.000
CHEMBL2949 Cyclooxygenase-1 Ovis aries 1.000
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 1.000
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.975
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.928
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.926
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.838
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.781
CHEMBL5631 Uncharacterized protein Rv1284/MT1322 Mycobacterium tuberculosis 0.695
CHEMBL5767 PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) Mycobacterium tuberculosis 0.648
CHEMBL3912 Carbonic anhydrase XIII Homo sapiens 0.585
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.506



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL230 Cyclooxygenase-2 Homo sapiens 1.000
CHEMBL221 Cyclooxygenase-1 Homo sapiens 1.000
CHEMBL4033 Cyclooxygenase-2 Canis lupus familiaris 1.000
CHEMBL4102 Cyclooxygenase-2 Ovis aries 1.000
CHEMBL2949 Cyclooxygenase-1 Ovis aries 1.000
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 1.000
CHEMBL4321 Cyclooxygenase-2 Mus musculus 1.000
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 1.000
CHEMBL205 Carbonic anhydrase II Homo sapiens 1.000
CHEMBL261 Carbonic anhydrase I Homo sapiens 1.000
CHEMBL4133 Cyclooxygenase-1 Canis lupus familiaris 1.000
CHEMBL5767 PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) Mycobacterium tuberculosis 0.999
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.997
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.996
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.886
CHEMBL5337 Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) 0.869
CHEMBL5631 Uncharacterized protein Rv1284/MT1322 Mycobacterium tuberculosis 0.840
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.685
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.566
CHEMBL5973 Carbonic anhydrase 15 Mus musculus 0.432

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
381.4 381.0759 3.51 3 77.98 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 0 5 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.68 - 2.59 2.59 3 26 0.75

Structural Alerts

There are no structural alerts for CHEMBL118

Compound Cross References

ATC M - MUSCULO-SKELETAL SYSTEM
M01 - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01A - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01AH - Coxibs
M01AH01 - celecoxib

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX33 - celecoxib

ChemSpider ChemSpider:RZEKVGVHFLEQIL-UHFFFAOYSA-N
DailyMed celecoxib
PubChem SID: 144204686 SID: 144209162 SID: 144210916 SID: 170464693 SID: 17389545 SID: 26747363 SID: 49665790 SID: 49666478 SID: 535138
Wikipedia Celecoxib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL118



ACToR 184007-95-2 169590-42-5
Atlas celecoxib
BindingDB 11639
Brenda 83080 154370 153386 69450 1809
ChEBI 41423
ChemicalBook CB7444681
DrugBank DB00482
DrugCentral 568
eMolecules 901601
EPA CompTox Dashboard DTXSID0022777
FDA SRS JCX84Q7J1L
Guide to Pharmacology 2892
Human Metabolome Database HMDB0005014
IBM Patent System F4D1CD0A7C38C39EF23ED0694095B545
KEGG Ligand C07589
LINCS LSM-2032
Mcule MCULE-4750749400
MolPort MolPort-002-885-815
NIH Clinical Collection SAM002589995
Nikkaji J833.239H
PDBe CEL
PharmGKB PA448871
PubChem 2662
PubChem: Drugs of the Future 12015009
PubChem: Thomson Pharma 14755918
Selleck Celecoxib
SureChEMBL SCHEMBL3708
ZINC ZINC000002570895

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