Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC1=CC=C(NC(C)=O)C=C1
InChI
InChIKey=CPJSUEIXXCENMM-UHFFFAOYSA-N
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)
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Phenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine for many years. Since a major portion of a dose of phenacetin is rapidly metabolised to paracetamol, it seems possible that phenacetin owes some of its therapeutic activity to its main metabolite, paracetamol, whereas its most troublesome side effect (methaemoglobinaemia) is due to another metabolite, p-phenetidine. Phenacetin was shown to inhibit cyclooxygenase (COX)-3, a cyclooxygenase-1 variant while p-phenetidine potently inhibits both COX-1 and COX-2. There is sufficient evidence in humans for the carcinogenicity of analgesic mixtures containing phenacetin. Analgesic mixtures containing phenacetin cause cancer of the renal pelvis, and of the ureter. Phenacetin was withdrawn from many analgesic mixtures long before the legal ban in several countries.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. | 1964 Aug |
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| [Determination of three components in compound chlorophenamine tablet by iterative target transformation factor analysis]. | 2001 Apr |
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| [Simultaneous determination of aspirin, phenacetin and caffeine in compound APC by derivative ratio UV adsorption spectrum method]. | 2001 Aug |
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| Renal PGE2 production in the human and rat following phenacetin, acetaminophen and p-aminophenol. | 2002 |
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| Drug-induced hepatitis with hepatic granuloma due to saridon. | 2002 |
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| Alteration of phenacetin pharmacokinetics after experimental spinal cord injury. | 2002 |
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| Fondaparinux sodium is not metabolised in mammalian liver fractions and does not inhibit cytochrome P450-mediated metabolism of concomitant drugs. | 2002 |
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| Decreased hepatic drug metabolising enzyme activity in rats with nitrosamine-induced tumours. | 2002 |
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| Validated HPLC method for determination of chlorzoxazone in human serum and its application in a clinical pharmacokinetic study. | 2002 Dec |
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| Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. | 2002 Dec |
|
| [Simultaneous determination of four components in the compound child phenobarbital tablet using ultraviolet spectrophotometry]. | 2002 Feb 28 |
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| Hydrogen bonding with adsorbent during storage governs drug dissolution from solid-dispersion granules. | 2002 Nov |
|
| Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs. | 2002 Nov |
|
| Phenotype of CYP2C19 and CYP3A4 by determination of omeprazole and its two main metabolites in plasma using liquid chromatography with liquid-liquid extraction. | 2002 Nov 25 |
|
| Monolithic silica rod liquid chromatography with ultraviolet or fluorescence detection for metabolite analysis of cytochrome P450 marker reactions. | 2002 Nov 25 |
|
| Hospitalized poisonings after renal transplantation in the United States. | 2002 Nov 26 |
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| Renal papillary necrosis. | 2002 Nov-Dec |
|
| COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. | 2002 Oct 15 |
|
| Polymer particle erosion controlling drug release. II. Swelling investigations to clarify the release mechanism. | 2002 Oct 24 |
|
| Correlation between induction of DNA fragmentation in urinary bladder cells from rats and humans and tissue-specific carcinogenic activity. | 2002 Sep 30 |
|
| Epidemiology of non-steroidal anti-inflammatory drugs and cancer. | 2003 |
|
| Analgesics and renal disease in the postphenacetin era. | 2003 Aug |
|
| 'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies. | 2003 Dec |
|
| Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. | 2003 Dec 9 |
|
| Identification of cytochrome P450 1A2 as enzyme involved in the microsomal metabolism of Huperzine A. | 2003 Feb 14 |
|
| High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry. | 2003 Jan 1 |
|
| Simultaneous liquid chromatography-tandem mass spectrometric determination of albendazole sulfoxide and albendazole sulfone in plasma. | 2003 Jan 5 |
|
| Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation. | 2003 Jul |
|
| Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones. | 2003 Jul |
|
| Caffeine as a promoter of analgesic-associated nephropathy--where is the evidence? | 2003 Jun |
|
| [Novel potential uses of thalidomide in the management of pain? A review of the literature]. | 2003 Jun |
|
| Effects of phenacetin and its metabolite p-phenetidine on COX-1 and COX-2 activities and expression in vitro. | 2003 Jun 15 |
|
| Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. | 2003 Nov |
|
| Effects of non-steroidal anti-inflammatory drugs on cancer sites other than the colon and rectum: a meta-analysis. | 2003 Oct 31 |
|
| HPLC analyses and pharmacokinetic studies of baicalin and oxymatrine in rabbits. | 2003 Sep |
|
| Assessment of tableting properties using infinitesimal quantities of powdered medicine. | 2003 Sep 16 |
|
| Induction of diphenytriazol on cytochrome CYP1A. | 2004 Apr |
|
| Analgesic nephropathy in Hungary: the HANS study. | 2004 Apr |
|
| Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes. | 2004 Apr 16 |
|
| Phenacetin and cocaine in a body packer. | 2004 Apr 20 |
|
| Atomoxetine hydrochloride: clinical drug-drug interaction prediction and outcome. | 2004 Feb |
|
| Functional characterization of four allelic variants of human cytochrome P450 1A2. | 2004 Feb 1 |
|
| Interaction of cyclooxygenase isoenzymes, nitric oxide, and afferent neurons in gastric mucosal defense in rats. | 2004 Jan |
|
| Six novel nonsynonymous CYP1A2 gene polymorphisms: catalytic activities of the naturally occurring variant enzymes. | 2004 Jan |
|
| Antipyretic therapy. | 2004 Jan 1 |
|
| Validated assays for human cytochrome P450 activities. | 2004 Jun |
|
| Evaluation of the patient with hematuria. | 2004 Mar |
|
| In vitro metabolism and inductive or inhibitive effect of DL111 on rat cytochrome P4501A enzyme. | 2004 Mar 15 |
|
| Evaluation of the Xpa-deficient transgenic mouse model for short-term carcinogenicity testing: 9-month studies with haloperidol, reserpine, phenacetin, and D-mannitol. | 2004 Mar-Apr |
|
| [Prevention of bladder cancer]. | 2004 May |
Patents
Sample Use Guides
Analgesic mixtures containing phenacetin were previously marketed as tablets or capsules containing between 150 and 300 mg phenacetin. Common combinations were: 150 mg phenacetin, 230 mg aspirin, and 15 or 30 mg caffeine; or 150 mg phenacetin, 230 mg aspirin, 30 mg caffeine, and 8, 15, 30, or 60 mg codeine phosphate. Phenacetin alone was also available in 250 and 300 mg doses as tablets, and up to 500 mg doses as powder. The usual dose was 300 mg 4–6 times per day, and the daily dose was not to exceed 2 g
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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on
Edited
Tue Oct 22 00:43:31 UTC 2019
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on
Tue Oct 22 00:43:31 UTC 2019
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| Record UNII |
ER0CTH01H9
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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WHO-ATC |
N02BE53
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WHO-VATC |
QN02BE53
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WHO-ATC |
N02BE03
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WHO-VATC |
QN02BE73
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IARC | Phenacetin | ||
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WHO-ATC |
N02BE73
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NCI_THESAURUS |
C45176
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WHO-VATC |
QN02BE03
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SUB09745MIG
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7402
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62-44-2
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412
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C44432
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PHENACETIN
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62-44-2
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8113
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CHEMBL16073
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D010615
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62-44-2
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M8589
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PRIMARY | Merck Index | ||
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200-533-0
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4754
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE TOXIC -> PARENT |
Metabolite induced methaemoglobinaemia in man.
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METABOLITE ACTIVE -> PARENT |
Percent of dose excreted in urine as metabolite.
AMOUNT ADMINISTERED
URINE
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METABOLITE ACTIVE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
