CHEBI:8050 - phenacetin

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ChEBI Name phenacetin
ChEBI ID CHEBI:8050
Definition A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a 4-ethoxyphenyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H13NO2
Net Charge 0
Average Mass 179.21576
Monoisotopic Mass 179.095
InChI InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
InChIKey CPJSUEIXXCENMM-UHFFFAOYSA-N
SMILES CCOc1ccc(NC(C)=O)cc1
Roles Classification
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
cyclooxygenase 3 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.
Application(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
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ChEBI Ontology
Outgoing phenacetin (CHEBI:8050) has functional parent 4-ethoxyaniline (CHEBI:85505)
phenacetin (CHEBI:8050) has functional parent N-phenylacetamide (CHEBI:28884)
phenacetin (CHEBI:8050) has role cyclooxygenase 3 inhibitor (CHEBI:73263)
phenacetin (CHEBI:8050) has role non-narcotic analgesic (CHEBI:35481)
phenacetin (CHEBI:8050) has role peripheral nervous system drug (CHEBI:49110)
phenacetin (CHEBI:8050) is a acetamides (CHEBI:22160)
phenacetin (CHEBI:8050) is a aromatic ether (CHEBI:35618)
IUPAC Name
N-(4-ethoxyphenyl)acetamide
INNs Sources
Fenacetina ChemIDplus
phenacetin ChEBI
Phenacetine ChemIDplus
Phenacetinum ChemIDplus
Synonyms Sources
1-Acetamido-4-ethoxybenzene ChemIDplus
4-Ethoxyacetanilide ChemIDplus
Acetophenetidin KEGG COMPOUND
Acetophenetidine DrugBank
Acetophenetin DrugBank
Acetphenetidin DrugBank
Phenacetin KEGG COMPOUND
Brand Names Sources
Achrocidin DrugBank
Codempiral DrugBank
Commotional DrugBank
Contradol DrugBank
Contradouleur DrugBank
Database Links Databases
C07591 KEGG COMPOUND
D00569 KEGG DRUG
DB03783 DrugBank
LSM-2851 LINCS
N4E PDBeChem
Phenacetin Wikipedia
US2887513 Patent
View more database links
Registry Numbers Types Sources
1869238 Reaxys Registry Number Reaxys
62-44-2 CAS Registry Number KEGG COMPOUND
62-44-2 CAS Registry Number ChemIDplus
62-44-2 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
24201458 PubMed citation Europe PMC
24447449 PubMed citation Europe PMC
Last Modified
25 February 2016
General Comment
2011-07-20 One of the first non-narcotic analgesics without anti-inflammatory properties (1887), phenacetin was widely used as a remedy for fever and pain for nearly a century, usually with aspirin, caffeine or codeine. It is now little used because of nephrotoxicity and adverse haematological effects.