Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Optical Activity | NONE |
| 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 | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/books/NBK304337Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18140117 | https://www.ncbi.nlm.nih.gov/pubmed/3552585 | https://www.ncbi.nlm.nih.gov/pubmed/12242329 | https://www.ncbi.nlm.nih.gov/pubmed/14592552
Sources: https://www.ncbi.nlm.nih.gov/books/NBK304337
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18140117 | https://www.ncbi.nlm.nih.gov/pubmed/3552585 | https://www.ncbi.nlm.nih.gov/pubmed/12242329 | https://www.ncbi.nlm.nih.gov/pubmed/14592552
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 Phenacetin was withdrawn from many analgesic mixtures long before the legal ban in several countries.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q8HZR1 Gene ID: 403544.0 Gene Symbol: PTGS1 Target Organism: Canis lupus familiaris (Dog) (Canis familiaris) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12242329 |
102.0 µM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14592552 |
|||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14592552 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Phenacetin Approved UsePhenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine for many years. Launch Date1886 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.5 μg/mL |
1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.5 μg/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.9 μg/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACETAMINOPHEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.84 μg/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.48 μg/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20.72 μg × h/mL |
1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.3 μg × h/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
40.4 μg × h/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACETAMINOPHEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.84 μg × h/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.58 μg × h/mL |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.6 h |
1.5 g single, oral dose: 1.5 g route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.9 h |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.6 h |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACETAMINOPHEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.1 h |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.98 h |
900 mg single, oral dose: 900 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENACETIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
70% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23607050/ |
PHENACETIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1.5 g 1 times / day multiple, oral Studied dose Dose: 1.5 g, 1 times / day Route: oral Route: multiple Dose: 1.5 g, 1 times / day Sources: |
unhealthy, 34 years |
Other AEs: Nephropathy... |
250 mg multiple, oral Studied dose |
unhealthy, 54 years |
Other AEs: Nephropathy... |
1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 56 years |
Other AEs: Transitional cell carcinoma... |
625 mg 1 times / day multiple, oral Studied dose Dose: 625 mg, 1 times / day Route: oral Route: multiple Dose: 625 mg, 1 times / day Sources: |
unhealthy, 85 years |
Other AEs: Urothelial carcinoma... |
0.9 g 4 times / day multiple, oral Studied dose Dose: 0.9 g, 4 times / day Route: oral Route: multiple Dose: 0.9 g, 4 times / day Sources: |
healthy, age 18 to 44 years Health Status: healthy Age Group: age 18 to 44 years Sex: M+F Sources: |
Other AEs: Nephritis NEC... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nephropathy | 1.5 g 1 times / day multiple, oral Studied dose Dose: 1.5 g, 1 times / day Route: oral Route: multiple Dose: 1.5 g, 1 times / day Sources: |
unhealthy, 34 years |
|
| Nephropathy | 250 mg multiple, oral Studied dose |
unhealthy, 54 years |
|
| Transitional cell carcinoma | 1 g 1 times / day multiple, oral Studied dose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 56 years |
|
| Urothelial carcinoma | 625 mg 1 times / day multiple, oral Studied dose Dose: 625 mg, 1 times / day Route: oral Route: multiple Dose: 625 mg, 1 times / day Sources: |
unhealthy, 85 years |
|
| Nephritis NEC | 20% | 0.9 g 4 times / day multiple, oral Studied dose Dose: 0.9 g, 4 times / day Route: oral Route: multiple Dose: 0.9 g, 4 times / day Sources: |
healthy, age 18 to 44 years Health Status: healthy Age Group: age 18 to 44 years Sex: M+F Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/10421611/ Page: 1.0 |
inconclusive | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10421611/ Page: 1.0 |
inconclusive | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10421611/ Page: 1.0 |
inconclusive | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10421611/ Page: 1.0 |
inconclusive | |||
Page: 1.0 |
major | yes (co-administration study) Comment: cigarette smoking induced CYP1A2 and increased O-deethylase activity Page: 1.0 |
||
Sources: https://pubmed.ncbi.nlm.nih.gov/10627170/ Page: 1.0 |
minor | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10421611/ Page: 1.0 |
minor |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of the Xpa-deficient transgenic mouse model for short-term carcinogenicity testing: 9-month studies with haloperidol, reserpine, phenacetin, and D-mannitol. | 2004-06-18 |
|
| Validated assays for human cytochrome P450 activities. | 2004-06 |
|
| [Prevention of bladder cancer]. | 2004-05 |
|
| Phenacetin and cocaine in a body packer. | 2004-04-20 |
|
| Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes. | 2004-04-16 |
|
| Induction of diphenytriazol on cytochrome CYP1A. | 2004-04 |
|
| Analgesic nephropathy in Hungary: the HANS study. | 2004-04 |
|
| In vitro metabolism and inductive or inhibitive effect of DL111 on rat cytochrome P4501A enzyme. | 2004-03-15 |
|
| Evaluation of the patient with hematuria. | 2004-03 |
|
| Functional characterization of four allelic variants of human cytochrome P450 1A2. | 2004-02-01 |
|
| Atomoxetine hydrochloride: clinical drug-drug interaction prediction and outcome. | 2004-02 |
|
| Antipyretic therapy. | 2004-01-01 |
|
| Interaction of cyclooxygenase isoenzymes, nitric oxide, and afferent neurons in gastric mucosal defense in rats. | 2004-01 |
|
| Six novel nonsynonymous CYP1A2 gene polymorphisms: catalytic activities of the naturally occurring variant enzymes. | 2004-01 |
|
| Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. | 2003-12-09 |
|
| 'Open access' generic method for continuous determination of major human CYP450 probe substrates/metabolites and its application in drug metabolism studies. | 2003-12 |
|
| Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. | 2003-11 |
|
| Effects of non-steroidal anti-inflammatory drugs on cancer sites other than the colon and rectum: a meta-analysis. | 2003-10-31 |
|
| Assessment of tableting properties using infinitesimal quantities of powdered medicine. | 2003-09-16 |
|
| HPLC analyses and pharmacokinetic studies of baicalin and oxymatrine in rabbits. | 2003-09 |
|
| Analgesics and renal disease in the postphenacetin era. | 2003-08 |
|
| Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation. | 2003-07 |
|
| Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones. | 2003-07 |
|
| Effects of phenacetin and its metabolite p-phenetidine on COX-1 and COX-2 activities and expression in vitro. | 2003-06-15 |
|
| Caffeine as a promoter of analgesic-associated nephropathy--where is the evidence? | 2003-06 |
|
| [Novel potential uses of thalidomide in the management of pain? A review of the literature]. | 2003-06 |
|
| Identification of cytochrome P450 1A2 as enzyme involved in the microsomal metabolism of Huperzine A. | 2003-02-14 |
|
| Renal papillary necrosis. | 2003-01-07 |
|
| Simultaneous liquid chromatography-tandem mass spectrometric determination of albendazole sulfoxide and albendazole sulfone in plasma. | 2003-01-05 |
|
| High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry. | 2003-01-01 |
|
| Epidemiology of non-steroidal anti-inflammatory drugs and cancer. | 2003 |
|
| Validated HPLC method for determination of chlorzoxazone in human serum and its application in a clinical pharmacokinetic study. | 2002-12 |
|
| Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. | 2002-12 |
|
| Hospitalized poisonings after renal transplantation in the United States. | 2002-11-26 |
|
| Phenotype of CYP2C19 and CYP3A4 by determination of omeprazole and its two main metabolites in plasma using liquid chromatography with liquid-liquid extraction. | 2002-11-25 |
|
| Monolithic silica rod liquid chromatography with ultraviolet or fluorescence detection for metabolite analysis of cytochrome P450 marker reactions. | 2002-11-25 |
|
| Hydrogen bonding with adsorbent during storage governs drug dissolution from solid-dispersion granules. | 2002-11 |
|
| Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs. | 2002-11 |
|
| Polymer particle erosion controlling drug release. II. Swelling investigations to clarify the release mechanism. | 2002-10-24 |
|
| COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. | 2002-10-15 |
|
| Correlation between induction of DNA fragmentation in urinary bladder cells from rats and humans and tissue-specific carcinogenic activity. | 2002-09-30 |
|
| [Simultaneous determination of four components in the compound child phenobarbital tablet using ultraviolet spectrophotometry]. | 2002-02-28 |
|
| Renal PGE2 production in the human and rat following phenacetin, acetaminophen and p-aminophenol. | 2002 |
|
| Drug-induced hepatitis with hepatic granuloma due to saridon. | 2002 |
|
| Alteration of phenacetin pharmacokinetics after experimental spinal cord injury. | 2002 |
|
| Fondaparinux sodium is not metabolised in mammalian liver fractions and does not inhibit cytochrome P450-mediated metabolism of concomitant drugs. | 2002 |
|
| Decreased hepatic drug metabolising enzyme activity in rats with nitrosamine-induced tumours. | 2002 |
|
| [Simultaneous determination of aspirin, phenacetin and caffeine in compound APC by derivative ratio UV adsorption spectrum method]. | 2001-08 |
|
| [Determination of three components in compound chlorophenamine tablet by iterative target transformation factor analysis]. | 2001-04 |
|
| IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. | 1964-08 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/books/NBK304337/
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
Mon Mar 31 17:46:06 GMT 2025
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| Record UNII |
ER0CTH01H9
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Validated (UNII)
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WHO-ATC |
N02BE53
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CFR |
21 CFR 216.24
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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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8050
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ER0CTH01H9
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1514008
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7651
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412
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C44432
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ER0CTH01H9
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2115
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PHENACETIN
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3152
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8113
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CHEMBL16073
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D010615
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DB03783
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m8589
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PRIMARY | Merck Index | ||
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100000088566
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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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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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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 |
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