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Record Information
Version2.0
Creation Date2014-09-11 02:05:50 UTC
Update Date2014-12-24 20:26:55 UTC
Accession NumberT3D4707
Identification
Common NamePhenacetin
ClassSmall Molecule
DescriptionPhenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).
Compound Type
  • Amide
  • Amine
  • Analgesic, Non-Narcotic
  • Drug
  • Ether
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Acetophenetidin
Acetophenetidine
Acetophenetin
Acetphenetidin
Achrocidin
Codempiral
Commotional
Contradol
Contradouleur
Chemical FormulaC10H13NO2
Average Molecular Mass179.216 g/mol
Monoisotopic Mass179.095 g/mol
CAS Registry Number62-44-2
IUPAC NameN-(4-ethoxyphenyl)acetamide
Traditional Namephenacetin
SMILESCCOC1=CC=C(C=C1)N=C(C)O
InChI IdentifierInChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
InChI KeyInChIKey=CPJSUEIXXCENMM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAcetanilides
Alternative Parents
Substituents
  • Acetanilide
  • N-acetylarylamine
  • Phenoxy compound
  • Phenol ether
  • N-arylamide
  • Alkyl aryl ether
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point137.5°C
Boiling PointNot Available
Solubility766 mg/L (at 25°C)
LogP1.58
Predicted Properties
PropertyValueSource
Water Solubility1.78 g/LALOGPS
logP1.62ALOGPS
logP1.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.98ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.13 m³·mol⁻¹ChemAxon
Polarizability19.82 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-001i-0900000000-335c6f93c6c61172facaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-6900100000-e5425770c8b511b991faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-ff1bc2f7f827dd1711f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qi-0900000000-8d7f58b56528e6f12b90JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0900000000-632d2f940d3bf1e4b090JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-2900000000-a8b75ec081cf2f9bd170JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0c03-2900000000-115f1b03c65a7dc2e1e9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0900000000-375522dc595b7e227b62JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-6900100000-e5425770c8b511b991faJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-0900000000-06f027a46bdc57e87bceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c452f944a1db68cee3c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0api-5900000000-f70777770ccda7bb06c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-cd4d0176028d2239a02bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kbr-1900000000-ffdf4ba50461a7f4a9e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-b21ee1fba6c9e0e2a84fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-a251ba59f8f792deb3e1JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityPhenacetin's analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action on the heart, where it acts as a negative inotrope. It is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type) and intercostal neuralgia.
MetabolismMetabolised in the body to paracetamol.
Toxicity ValuesAcute oral toxicity (LD50): 866 mg/kg [Mouse].
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (5)
Uses/SourcesUsed principally as an analgesic.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03783
HMDB IDNot Available
PubChem Compound ID4754
ChEMBL IDCHEMBL16073
ChemSpider ID4590
KEGG IDC07591
UniProt IDNot Available
OMIM ID
ChEBI ID8050
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkPhenacetin
References
Synthesis Reference

Ernst Bocker, Wolfgang Kracht, Roland Rupp, Erhard Schellmann, Viktor Trescher, Martin Ullrich, “Preparation of melt-sprayed spherical phenacetin granules.” U.S. Patent US4086346, issued October, 1972.

MSDST3D4707.pdf
General References
  1. Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. 1991 Jan 17;324(3):155-60. [1984193 ]
  2. Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. [6036245 ]
  3. TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. 1964 Aug;101:73-7. [14180501 ]
  4. Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. [12512867 ]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]