Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 02:05:50 UTC |
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Update Date | 2014-12-24 20:26:55 UTC |
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Accession Number | T3D4707 |
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Identification |
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Common Name | Phenacetin |
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Class | Small Molecule |
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Description | Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney). |
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Compound Type | - Amide
- Amine
- Analgesic, Non-Narcotic
- Drug
- Ether
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | Acetophenetidin | Acetophenetidine | Acetophenetin | Acetphenetidin | Achrocidin | Codempiral | Commotional | Contradol | Contradouleur |
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Chemical Formula | C10H13NO2 |
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Average Molecular Mass | 179.216 g/mol |
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Monoisotopic Mass | 179.095 g/mol |
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CAS Registry Number | 62-44-2 |
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IUPAC Name | N-(4-ethoxyphenyl)acetamide |
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Traditional Name | phenacetin |
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SMILES | CCOC1=CC=C(C=C1)N=C(C)O |
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InChI Identifier | 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) |
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InChI Key | InChIKey=CPJSUEIXXCENMM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Anilides |
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Direct Parent | Acetanilides |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 137.5°C | Boiling Point | Not Available | Solubility | 766 mg/L (at 25°C) | LogP | 1.58 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-001i-0900000000-335c6f93c6c61172faca | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-03di-6900100000-e5425770c8b511b991fa | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-ff1bc2f7f827dd1711f6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01qi-0900000000-8d7f58b56528e6f12b90 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0900000000-632d2f940d3bf1e4b090 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-2900000000-a8b75ec081cf2f9bd170 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0c03-2900000000-115f1b03c65a7dc2e1e9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-001i-0900000000-375522dc595b7e227b62 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-03di-6900100000-e5425770c8b511b991fa | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001r-0900000000-06f027a46bdc57e87bce | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-c452f944a1db68cee3c0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0api-5900000000-f70777770ccda7bb06c7 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0900000000-cd4d0176028d2239a02b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0kbr-1900000000-ffdf4ba50461a7f4a9e0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-3900000000-b21ee1fba6c9e0e2a84f | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-3900000000-a251ba59f8f792deb3e1 | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Phenacetin'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. |
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Metabolism | Metabolised in the body to paracetamol. |
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Toxicity Values | Acute oral toxicity (LD50): 866 mg/kg [Mouse]. |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | 1, carcinogenic to humans. (5) |
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Uses/Sources | Used principally as an analgesic. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB03783 |
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HMDB ID | Not Available |
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PubChem Compound ID | 4754 |
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ChEMBL ID | CHEMBL16073 |
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ChemSpider ID | 4590 |
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KEGG ID | C07591 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 8050 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Phenacetin |
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References |
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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. |
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MSDS | T3D4707.pdf |
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General References | - 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 ]
- Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. [6036245 ]
- 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 ]
- Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. [12512867 ]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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