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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
Structure of PHENACETIN

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)

HIDE SMILES / InChI

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

Description
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 Phenacetin was withdrawn from many analgesic mixtures long before the legal ban in several countries.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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q8HZR1
Gene ID: 403544.0
Gene Symbol: PTGS1
Target Organism: Canis lupus familiaris (Dog) (Canis familiaris)
102.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phenacetin

Approved Use

Phenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine for many years.

Launch Date

1886
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
PHENACETIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 34 years
Sex: F
Sources:
Other AEs: Nephropathy...
Other AEs:
Nephropathy
Sources:
250 mg multiple, oral
Studied dose
Dose: 250 mg
Route: oral
Route: multiple
Dose: 250 mg
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: F
Sources:
Other AEs: Nephropathy...
Other AEs:
Nephropathy
Sources:
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
Health Status: unhealthy
Age Group: 56 years
Sex: M
Sources:
Other AEs: Transitional cell carcinoma...
Other AEs:
Transitional cell carcinoma
Sources:
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
Health Status: unhealthy
Age Group: 85 years
Sex: M
Sources:
Other AEs: Urothelial carcinoma...
Other AEs:
Urothelial carcinoma
Sources:
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...
Other AEs:
Nephritis NEC (20%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 34 years
Sex: F
Sources:
Nephropathy
250 mg multiple, oral
Studied dose
Dose: 250 mg
Route: oral
Route: multiple
Dose: 250 mg
Sources:
unhealthy, 54 years
Health Status: unhealthy
Age Group: 54 years
Sex: F
Sources:
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
Health Status: unhealthy
Age Group: 56 years
Sex: M
Sources:
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
Health Status: unhealthy
Age Group: 85 years
Sex: M
Sources:
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

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
inconclusive
inconclusive
inconclusive
major
yes (co-administration study)
Comment: cigarette smoking induced CYP1A2 and increased O-deethylase activity
Page: 1.0
minor
minor
PubMed

PubMed

TitleDatePubMed
IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG.
1964 Aug
Analgesic abuse, ureteric obstruction, and retroperitoneal fibrosis.
1975 Apr 12
Letter: The clinical course of patients with analgesic nephropathy.
1975 Aug 9
The induction of renal papillary necrosis in Gunn rats by analgesics and analgesic mixtures.
1975 Feb
The radiological diagnosis of analgesic nephropathy.
1975 Jul
Epidemiology and etiology of premalignant and malignant urothelial changes.
2000
A population approach to enzyme characterization and identification: application to phenacetin O-deethylation.
2000 Dec
[Determination of three components in compound chlorophenamine tablet by iterative target transformation factor analysis].
2001 Apr
Oxidations of p-alkoxyacylanilides catalyzed by human cytochrome P450 1A2: structure-activity relationships and simulation of rate constants of individual steps in catalysis.
2001 Apr 10
Polymer particle erosion controlling drug release. I. Factors influencing drug release and characterization of the release mechanism.
2001 Apr 17
[Simultaneous determination of aspirin, phenacetin and caffeine in compound APC by derivative ratio UV adsorption spectrum method].
2001 Aug
"No, Duke. No divorce".
2001 Aug 20
Analysis of the phase solubility diagram of a phenacetin/competitor/beta-cyclodextrin ternary system, involving competitive inclusion complexation.
2001 Jan
Relationship between nonphenacetin-combined analgesics and nephropathy.
2001 Jun
Relationship between nonphenacetin-combined analgesics and nephropathy.
2001 Jun
Relationship between nonphenacetin-combined analgesics and nephropathy.
2001 Jun
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.
2001 Mar
Trends of analgesic nephropathy in two high-endemic regions with different legislation.
2001 Mar
Suppression of agglomeration in fluidized bed coating. IV. Effects of sodium citrate concentration on the suppression of particle agglomeration and the physical properties of HPMC film.
2001 Mar 14
[Analgesics-induced chronic renal failure in patients on dialysis therapy in Hungary].
2001 May 13
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Drug-induced hepatitis with hepatic granuloma due to saridon.
2002
Comparison of vasoconstrictor responses to selected NSAIDs in rabbit renal and femoral arteries.
2002
The onset of action and the analgesic efficacy of Saridon (a propyphenazone/paracetamol/ caffeine combination) in comparison with paracetamol, ibuprofen, aspirin and placebo (pooled statistical analysis).
2002
A straightforward means of coupling preparative high-performance liquid chromatography and mass spectrometry.
2002
Phenacetin O-deethylation in extrahepatic tissues of rats.
2002 Apr-Jun
Validated HPLC method for determination of chlorzoxazone in human serum and its application in a clinical pharmacokinetic study.
2002 Dec
Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions.
2002 Dec
Method development and validation of a high-performance liquid chromatographic method for tramadol in human plasma using liquid-liquid extraction.
2002 May 25
Hydrogen bonding with adsorbent during storage governs drug dissolution from solid-dispersion granules.
2002 Nov
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
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
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
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
Phenacetin and cocaine in a body packer.
2004 Apr 20
Interaction of cyclooxygenase isoenzymes, nitric oxide, and afferent neurons in gastric mucosal defense in rats.
2004 Jan
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:06 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:06 GMT 2025
Record UNII
ER0CTH01H9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENACETIN
HSDB   INCI   INN   JAN   MART.   MI   VANDF   WHO-DD  
INN   INCI  
Official Name English
PHENACETINUM
HPUS  
Preferred Name English
PHENACETIN [VANDF]
Common Name English
4-ETHOXY-1-ACETYLAMINOBENZENE
Systematic Name English
FENIDINA
Common Name English
NSC-7651
Code English
PHENACETIN [MART.]
Common Name English
ACETAMIDE, N-(4-ETHOXYPHENOL)-
Common Name English
PHENACETIN [JAN]
Common Name English
ACETPHENETIDIN
Common Name English
KALMIN
Common Name English
PHENACETIN MELTING POINT STANDARD
USP-RS  
Common Name English
PHENACETIN [MI]
Common Name English
PHENACETINUM [HPUS]
Common Name English
PHENACETIN [USP-RS]
Common Name English
PHENACETIN [IARC]
Common Name English
PHENAZETIN
Common Name English
phenacetin [INN]
Common Name English
P-ACETOPHENETIDIDE
Common Name English
Phenacetin [WHO-DD]
Common Name English
PHENACETIN [HSDB]
Common Name English
ACETOPHENETIDIN
Common Name English
Classification Tree Code System Code
WHO-ATC N02BE53
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
CFR 21 CFR 216.24
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
WHO-VATC QN02BE53
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
WHO-ATC N02BE03
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
WHO-VATC QN02BE73
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
IARC Phenacetin
WHO-ATC N02BE73
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
NCI_THESAURUS C45176
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
WHO-VATC QN02BE03
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
Code System Code Type Description
EVMPD
SUB09745MIG
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
IUPHAR
7402
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
CAS
62-44-2
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
CHEBI
8050
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
FDA UNII
ER0CTH01H9
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
RS_ITEM_NUM
1514008
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
ALTERNATIVE
NSC
7651
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
INN
412
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
NCI_THESAURUS
C44432
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
DAILYMED
ER0CTH01H9
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
DRUG CENTRAL
2115
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
WIKIPEDIA
PHENACETIN
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
HSDB
3152
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
RS_ITEM_NUM
1513005
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
RXCUI
8113
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL16073
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
MESH
D010615
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID1021116
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
DRUG BANK
DB03783
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
MERCK INDEX
m8589
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY Merck Index
SMS_ID
100000088566
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-533-0
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
PUBCHEM
4754
Created by admin on Mon Mar 31 17:46:06 GMT 2025 , Edited by admin on Mon Mar 31 17:46:06 GMT 2025
PRIMARY
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