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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL16073
CHEMBL16073
Compound Name PHENACETIN
ChEMBL Synonyms Phenacetin Hydrochloride | ACETOPHENETIDIN | ACETPHENETIDIN | PHENACETIN
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names
Molecular Formula C10H13NO2

Additional synonyms for CHEMBL16073 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCOc1ccc(NC(=O)C)cc1
Standard InChI InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3 ...
Download InChI
Standard InChI Key CPJSUEIXXCENMM-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Open TG-GATEs
  • 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  • Withdrawn Drugs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


CHEMBL16073

Molecule Features

CHEMBL16073 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1980
Country United Kingdom; United States; Germany; Denmark
Reason Nephropathy
Class Nephrotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Unknown Not Available PubMed PubMed PubMed PubMed PubMed PubMed

Clinical Data

ClinicalTrials.gov PHENACETIN
The Cochrane Collaboration PHENACETIN

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 CHEMBL16073. 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
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.993
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.984
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.948
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.811
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.755
CHEMBL2392 DNA polymerase beta Homo sapiens 0.695
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.575
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.466
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.395
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.387
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.367
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 0.358
CHEMBL3358 Monoamine oxidase A Rattus norvegicus 0.323
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 0.250
CHEMBL5514 Huntingtin Homo sapiens 0.249
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 0.237
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.207



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.984
CHEMBL1293277 Niemann-Pick C1 protein Homo sapiens 0.973
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.937
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.892
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.787
CHEMBL2392 DNA polymerase beta Homo sapiens 0.412
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.379
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.336
CHEMBL3437 Amine oxidase, copper containing Homo sapiens 0.275
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.258
CHEMBL5514 Huntingtin Homo sapiens 0.230
CHEMBL3563 Cruzipain Trypanosoma cruzi 0.208
CHEMBL1293313 M17 leucyl aminopeptidase Plasmodium falciparum 3D7 0.201

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
179.2 179.0946 2.04 3 38.33 NEUTRAL


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 1.42 1.66 1.66 1 13 0.77

Structural Alerts

There are no structural alerts for CHEMBL16073

Compound Cross References

ATC N - NERVOUS SYSTEM
N02 - ANALGESICS
N02B - OTHER ANALGESICS AND ANTIPYRETICS
N02BE - Anilides
N02BE53 - phenacetin, combinations excl. psycholeptics

N - NERVOUS SYSTEM
N02 - ANALGESICS
N02B - OTHER ANALGESICS AND ANTIPYRETICS
N02BE - Anilides
N02BE73 - phenacetin, combinations with psycholeptics

N - NERVOUS SYSTEM
N02 - ANALGESICS
N02B - OTHER ANALGESICS AND ANTIPYRETICS
N02BE - Anilides
N02BE03 - phenacetin

ChemSpider ChemSpider:CPJSUEIXXCENMM-UHFFFAOYSA-N
PubChem SID: 11112166 SID: 124882016 SID: 144203898 SID: 144209124 SID: 144213212 SID: 170465554 SID: 17389770 SID: 26747350 SID: 26752987 SID: 50086861
Wikipedia Phenacetin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL16073



ACToR 62-44-2
Atlas phenacetin
BindingDB 50420191
Brenda 12655 111271 111270 126685 128794
ChEBI 8050
ChemicalBook CB6141828
DrugBank DB03783
DrugCentral 2115
eMolecules 490668
EPA CompTox Dashboard DTXSID1021116
FDA SRS ER0CTH01H9
Guide to Pharmacology 7402
IBM Patent System 7BF109734CF17DCC4FB6745447D2354A
KEGG Ligand C07591
LINCS LSM-2851
Mcule MCULE-2069106916
MolPort MolPort-000-626-710
Nikkaji J2.348E
NMRShiftDB 89616
PDBe N4E
PharmGKB PA450897
PubChem 4754
PubChem: Thomson Pharma 14748329
Selleck phenacetin
SureChEMBL SCHEMBL23280 SCHEMBL20476396
ZINC ZINC000000000602

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