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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL101
CHEMBL101
Compound Name PHENYLBUTAZONE
ChEMBL Synonyms Equiphar | Elmedal | PHENYLBUTAZONE | Pro-Bute | BUTAZOLIDIN | Butaject | DIPHENYLBUTAZONE | AZOLID | Antadol
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names Elmedal | AZOLID | Antadol | Butaject | BUTAZOLIDIN | Phenylbutazone | Pro-Bute | Equiphar
Molecular Formula C19H20N2O2

Additional synonyms for CHEMBL101 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCC1C(=O)N(N(C1=O)c2ccccc2)c3ccccc3
Standard InChI InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15) ...
Download InChI
Standard InChI Key VYMDGNCVAMGZFE-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Open TG-GATEs
  • Orange Book
  • 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  • Withdrawn Drugs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


CHEMBL101

Molecule Features

CHEMBL101 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First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn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 1985
Country Germany
Reason Off-Label Abuse; Hematologic Toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cyclooxygenase inhibitor Cyclooxygenase Expert

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
RHEUMATIC DISEASESD012216EFO:0005755RHEUMATIC DISEASE4ATC
ARTHRALGIAD018771HP:0002829ARTHRALGIA4ATC
MYALGIAD063806HP:0003326MYALGIA4ATC

Clinical Data

ClinicalTrials.gov PHENYLBUTAZONE
The Cochrane Collaboration PHENYLBUTAZONE

Metabolites for CHEMBL101

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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 CHEMBL101. 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
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.747
CHEMBL263 Type-1B angiotensin II receptor Rattus norvegicus 0.695
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.666
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.418
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.383
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.228



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL263 Type-1B angiotensin II receptor Rattus norvegicus 0.757
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.609
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.473
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.371

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
308.4 308.1525 3.95 5 40.62 ACID


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.64 - 3.38 1.07 2 23 0.79

Structural Alerts

There are 2 structural alerts for CHEMBL101. 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
M01AA - Butylpyrazolidines
M01AA01 - phenylbutazone

M - MUSCULO-SKELETAL SYSTEM
M02 - TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02A - TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02AA - Antiinflammatory preparations, non-steroids for topical use
M02AA01 - phenylbutazone

ChemSpider ChemSpider:VYMDGNCVAMGZFE-UHFFFAOYSA-N
PubChem SID: 104171220 SID: 104171221 SID: 11111674 SID: 144203793 SID: 144203794 SID: 144209007 SID: 144213080 SID: 170465040 SID: 17389760 SID: 26747057 SID: 26751573 SID: 50104199 SID: 56436656 SID: 85231197 SID: 855958 SID: 90341773
Wikipedia Phenylbutazone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL101



ACToR 4297-92-1 50-33-9
Atlas phenylbutazone
Brenda 4043
ChEBI 48574
DrugBank DB00812
DrugCentral 2145
eMolecules 593834 27523332
EPA CompTox Dashboard DTXSID9021136
FDA SRS GN5P7K3T8S
Guide to Pharmacology 7270
Human Metabolome Database HMDB0014950
IBM Patent System 6E3978466BAC36862F55D469EAA08BFA DF3F4D5F4641D849206602FD1911C7C8
KEGG Ligand C07440
LINCS LSM-2219
Mcule MCULE-4303869118
Metabolights MTBLC48574
Nikkaji J792G
NMRShiftDB 10016207
PDBe P1Z
PharmGKB PA450932
PubChem 4781
PubChem: Thomson Pharma 14898740
Selleck Phenylbutazone(Butazolidin)
SureChEMBL SCHEMBL3632
ZINC ZINC000100004227

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