ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1228
CHEMBL1228
Compound Name OXYPHENBUTAZONE
ChEMBL Synonyms OXAZOLIDIN | OXIPHENBUTAZONE | Oxyphenbutazone | Tandearil | TANDERIL CHLORAMPHEN | TANDERIL | TANDEARIL
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names Oxyphenbutazone | TANDERIL CHLORAMPHEN | TANDERIL | TANDEARIL | Tandearil
Molecular Formula C19H20N2O3

Additional synonyms for CHEMBL1228 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCC1C(=O)N(N(C1=O)c2ccc(O)cc2)c3ccccc3
Standard InChI InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21( ...
Download InChI
Standard InChI Key HFHZKZSRXITVMK-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • 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  • Withdrawn Drugs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


CHEMBL1228

Molecule Features

CHEMBL1228 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1984
Country United Kingdom; United States; Germany; France
Reason Blood Dyscrasis; Steven Johnson Syndrome
Class Dermatological toxicity; Hematological toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cyclooxygenase inhibitor Cyclooxygenase KEGG PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Rheumatic DiseasesD012216EFO:0005755rheumatic disease4ATC
Eye DiseasesD005128EFO:0005752eye inflammation4ATC
ArthralgiaD018771HP:0002829arthralgia4ATC
MyalgiaD063806HP:0003326Myalgia4ATC

Clinical Data

ClinicalTrials.gov OXYPHENBUTAZONE
The Cochrane Collaboration OXYPHENBUTAZONE

Metabolites for CHEMBL1228

Open in full screen

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 CHEMBL1228. 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
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.955
CHEMBL242 Estrogen receptor beta Homo sapiens 0.935
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.606
CHEMBL206 Estrogen receptor alpha Homo sapiens 0.392
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.390

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2085 Macrophage migration inhibitory factor Homo sapiens 0.998
CHEMBL242 Estrogen receptor beta Homo sapiens 0.941
CHEMBL206 Estrogen receptor alpha Homo sapiens 0.909
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.593
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.559
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.517
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.402
CHEMBL4159 Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens 0.312
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.226
CHEMBL3880 Heat shock protein HSP 90-alpha Homo sapiens 0.205

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
324.4 324.1474 3.49 5 60.85 ACID


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
5.08 .22 2.74 .47 2 24 0.86

Structural Alerts

There are 2 structural alerts for CHEMBL1228. To view alerts please click here.

Compound Cross References

ATC S - SENSORY ORGANS
S01 - OPHTHALMOLOGICALS
S01B - ANTIINFLAMMATORY AGENTS
S01BC - Antiinflammatory agents, non-steroids
S01BC02 - oxyphenbutazone

M - MUSCULO-SKELETAL SYSTEM
M01 - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01A - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01AA - Butylpyrazolidines
M01AA03 - oxyphenbutazone

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
M02AA04 - oxyphenbutazone

ChemSpider ChemSpider:HFHZKZSRXITVMK-UHFFFAOYSA-N
PubChem SID: 144203965 SID: 170465310 SID: 26748182 SID: 56463172
Wikipedia Oxyphenbutazone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1228



ACToR 129-20-4
BindingDB 200298
Brenda 94576 165883
ChEBI 76258
DrugBank DB03585
DrugCentral 2036
eMolecules 1988320 27523178
EPA CompTox Dashboard DTXSID1045291
IBM Patent System F5DF6615F698554C1A527E7C82B50DF8
KEGG Ligand C19494
LINCS LSM-5029
Mcule MCULE-3785704527
Metabolights MTBLC76258
MolPort MolPort-003-666-251
Nikkaji J10.648H
PharmGKB PA450750
PubChem 4641
PubChem: Thomson Pharma 14874898
SureChEMBL SCHEMBL25857

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