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Details

Stereochemistry ACHIRAL
Molecular Formula C8H9NO
Molecular Weight 135.1632
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETANILIDE

SMILES

CC(=O)NC1=CC=CC=C1

InChI

InChIKey=FZERHIULMFGESH-UHFFFAOYSA-N
InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)

HIDE SMILES / InChI

Molecular Formula C8H9NO
Molecular Weight 135.1632
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 http://www.seidlerchem.com/acetanilide.htm

Acetanilide is a synthetic organic compound introduced clinically in 1886 as a fever-reducing drug. Its effectiveness in relieving pain was discovered soon thereafter and it was used as an alternative to aspirin for many years in treating such common complaints as headaches, menstrual cramps, and rheumatism. Unfortunately, Acetanilide exhibited an unacceptable profile of toxic effects, the most alarming being cyanosis due to methemoglobinemia. The toxic profile prompted the search for supposedly less toxic aniline derivatives such as phenacetin. After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly metabolized to paracetamol (USAN: acetaminophen) in the human body and that it was the paracetamol that was responsible for the analgesic and antipyretic properties. Paracetamol has since replaced acetanilide usage because it is less likely to induce blood disorders. The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is hydrolyzed to aniline in the body. Acetanilide is no longer used as a drug in its own right, although its primary metabolite, paracetamol, has been widely succesful.

Originator

Sources: Cahn, A.; Hepp, P. (1886), 'Das Antifebrin, ein neues Fiebermittel', Centralbl. Klin. Med. 7: 561–64.
Curator's Comment: A. Cahn and P. Hepp in 1886

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.1 μg/mL
50 mg/kg m.a.m. single, oral
dose: 50 mg/kg m.a.m.
route of administration: Oral
experiment type: SINGLE
co-administered:
ACETANILIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.57 h
50 mg/kg m.a.m. single, oral
dose: 50 mg/kg m.a.m.
route of administration: Oral
experiment type: SINGLE
co-administered:
ACETANILIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4.78 h
50 mg/kg m.a.m. single, oral
dose: 50 mg/kg m.a.m.
route of administration: Oral
experiment type: SINGLE
co-administered:
ACETANILIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
90%
ACETANILIDE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
10 mL 1 times / day single, oral
Studied dose
Dose: 10 mL, 1 times / day
Route: oral
Route: single
Dose: 10 mL, 1 times / day
Sources:
unhealthy, 45 years
Health Status: unhealthy
Age Group: 45 years
Sex: F
Sources:
Other AEs: Gasping, Blurred vision...
Other AEs:
Gasping
Blurred vision
Cyanosis
Cardio-respiratory distress
Sources:
0.26 g 3 times / day multiple, oral
Studied dose
Dose: 0.26 g, 3 times / day
Route: oral
Route: multiple
Dose: 0.26 g, 3 times / day
Sources:
unhealthy, 55 years
Health Status: unhealthy
Age Group: 55 years
Sex: F
Sources:
Other AEs: Cyanosis...
5 mL 2 times / day multiple, oral
Studied dose
Dose: 5 mL, 2 times / day
Route: oral
Route: multiple
Dose: 5 mL, 2 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: F
Sources:
Other AEs: Vertigo, Tinnitus...
Other AEs:
Vertigo
Tinnitus
Temporal arteritis
Headache dull
Weakness
Sources:
AEs

AEs

AESignificanceDosePopulation
Blurred vision
10 mL 1 times / day single, oral
Studied dose
Dose: 10 mL, 1 times / day
Route: oral
Route: single
Dose: 10 mL, 1 times / day
Sources:
unhealthy, 45 years
Health Status: unhealthy
Age Group: 45 years
Sex: F
Sources:
Cardio-respiratory distress
10 mL 1 times / day single, oral
Studied dose
Dose: 10 mL, 1 times / day
Route: oral
Route: single
Dose: 10 mL, 1 times / day
Sources:
unhealthy, 45 years
Health Status: unhealthy
Age Group: 45 years
Sex: F
Sources:
Cyanosis
10 mL 1 times / day single, oral
Studied dose
Dose: 10 mL, 1 times / day
Route: oral
Route: single
Dose: 10 mL, 1 times / day
Sources:
unhealthy, 45 years
Health Status: unhealthy
Age Group: 45 years
Sex: F
Sources:
Gasping
10 mL 1 times / day single, oral
Studied dose
Dose: 10 mL, 1 times / day
Route: oral
Route: single
Dose: 10 mL, 1 times / day
Sources:
unhealthy, 45 years
Health Status: unhealthy
Age Group: 45 years
Sex: F
Sources:
Cyanosis
0.26 g 3 times / day multiple, oral
Studied dose
Dose: 0.26 g, 3 times / day
Route: oral
Route: multiple
Dose: 0.26 g, 3 times / day
Sources:
unhealthy, 55 years
Health Status: unhealthy
Age Group: 55 years
Sex: F
Sources:
Headache dull
5 mL 2 times / day multiple, oral
Studied dose
Dose: 5 mL, 2 times / day
Route: oral
Route: multiple
Dose: 5 mL, 2 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: F
Sources:
Temporal arteritis
5 mL 2 times / day multiple, oral
Studied dose
Dose: 5 mL, 2 times / day
Route: oral
Route: multiple
Dose: 5 mL, 2 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: F
Sources:
Tinnitus
5 mL 2 times / day multiple, oral
Studied dose
Dose: 5 mL, 2 times / day
Route: oral
Route: multiple
Dose: 5 mL, 2 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: F
Sources:
Vertigo
5 mL 2 times / day multiple, oral
Studied dose
Dose: 5 mL, 2 times / day
Route: oral
Route: multiple
Dose: 5 mL, 2 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: F
Sources:
Weakness
5 mL 2 times / day multiple, oral
Studied dose
Dose: 5 mL, 2 times / day
Route: oral
Route: multiple
Dose: 5 mL, 2 times / day
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Adsorption of acetanilide herbicides on soil and its components. II. Adsorption and catalytic hydrolysis of diethatyl-ethyl on saturated Na(+)-, K(+)-, Ca(2+)-, and Mg(2+)-montmorillonite.
2001 Apr
Stabilization of the hydrophilic sphere of non-ionic monomers: are all protected in a similar way?
2001 Dec
Redox-induced terpyridyl substitution in the Os(VI)-hydrazido complex, trans-[Os(VI)(tpy)(Cl)(2)(NN(CH(2))(4)O)](2+).
2001 Jul 30
A long-term lifetime amperometric glucose sensor with a perfluorocarbon polymer coating.
2001 Jun
Substitutions of Thr-103-Ile and Trp-138-Gly in amidase from Pseudomonas aeruginosa are responsible for altered kinetic properties and enzyme instability.
2001 Mar
Identification of the urinary metabolites of 4-bromoaniline and 4-bromo-[carbonyl-13C]-acetanilide in rat.
2002 Apr
Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.
2002 Feb 27
Size-selective catalysis of ester and anilide cleavage by the dinuclear barium(II) complexes of cis- and trans-stilbenobis(18-crown-6).
2002 Jan 25
Liquid chromatographic resolution of N-acyl-alpha-amino acids as their anilide derivatives on a chiral stationary phase based on (S)-leucine.
2002 Jun
1H-NMR assay of papaverine hydrochloride and formulations.
2002 Nov-Dec
Application of the PKCYP test to predict caffeine clearance mediated by CYP1A2 in a rat acute liver injury model.
2003
[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital].
2003 Aug
Electrochemical and spectroscopic studies of the oxidation mechanism of the herbicide propanil.
2003 Feb 12
Metabolites of a blocked chloramphenicol producer.
2003 Jan
Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli.
2003 Jul 30
Effects of land use on ground water quality in the Anoka Sand Plain Aquifer of Minnesota.
2003 Jul-Aug
Examination of molecular interaction sites of acetanilides with organic matter surrogates using nuclear magnetic resonance techniques.
2003 Jun 18
Herbicides and herbicide degradation products in Upper Midwest agricultural streams during August base-flow conditions.
2003 May-Jun
Novel hydroxamate and anilide derivatives as potent histone deacetylase inhibitors: synthesis and antiproliferative evaluation.
2003 Nov
Suitability of the cynomolgus monkey as an animal model for drug absorption studies of oral dosage forms from the viewpoint of gastrointestinal physiology.
2003 Oct
Energy of charged states in the acetanilide crystal: trapping of charge-transfer states at vacancies as a possible mechanism for optical damage.
2004 Apr 15
[Acetaminophen].
2004 Dec
High-performance liquid chromatographic-nuclear magnetic resonance investigation of the isomerization of alachlor-ethanesulfonic acid.
2004 Jan 2
[Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats].
2004 Jan-Feb
Orally active CCR5 antagonists as anti-HIV-1 agents 2: synthesis and biological activities of anilide derivatives containing a pyridine N-oxide moiety.
2004 Jul
Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides.
2004 Jun
Hydrogen-bonded polymer gel and its application as a temperature-sensitive drug delivery system.
2004 May
Bioisosteric replacement of anilide with benzoxazole: potent and orally bioavailable antagonists of VLA-4.
2004 May 3
[Salicylanilides: still a potential antibacterially active group].
2004 Nov
High-performance liquid chromatographic method for simultaneous determination of sophoridine and matrine in rat plasma.
2004 Nov
Synthesis and biological evaluation of 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one inhibitors of cyclin-dependent kinases.
2004 Nov 18
Controlling the conformation of arylamides: computational studies of intramolecular hydrogen bonds between amides and ethers or thioethers.
2004 Oct 11
Nucleophilic aromatic substitution on aryl-amido ligands promoted by oxidizing osmium(IV) centers.
2004 Sep 20
Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts.
2005 Apr 1
Behavior of acetanilide herbicides in soils and the possibility of groundwater contamination.
2005 Dec
Kinetic stability of heteroleptic (beta-diketiminato) heavier alkaline-earth (Ca, Sr, Ba) amides.
2005 Jan 21
Synthesis of structurally defined scaffolds for bivalent ligand display based on glucuronic acid anilides. The degree of tertiary amide isomerism and folding depends on the configuration of a glycosyl azide.
2005 May 13
Safety of the methylene blue plus chloroquine combination in the treatment of uncomplicated falciparum malaria in young children of Burkina Faso [ISRCTN27290841].
2005 Sep 22
Isolation of a bacterium that degrades urethane compounds and characterization of its urethane hydrolase.
2006 Apr
Discovery of novel and potent thiazoloquinazolines as selective Aurora A and B kinase inhibitors.
2006 Feb 9
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:55:32 GMT 2025
Edited
by admin
on Mon Mar 31 17:55:32 GMT 2025
Record UNII
SP86R356CC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETANILIDE
HSDB   MART.   MI   VANDF   WHO-DD  
Systematic Name English
ACETANILID
INCI  
INCI  
Preferred Name English
ACETANILIDE [USP-RS]
Common Name English
ACETANILIDE MELTING POINT STANDARD
USP-RS  
Common Name English
ACETANILIDE [MART.]
Common Name English
Acetanilide [WHO-DD]
Common Name English
NSC-203231
Code English
ACETANILIDE [HSDB]
Common Name English
N-PHENYLACETAMIDE
Systematic Name English
ACETAMINOPHEN RELATED COMPOUND D [USP-RS]
Common Name English
PARACETAMOL IMPURITY D [EP IMPURITY]
Common Name English
ACETYLANILINE
Systematic Name English
ACETANILIDE [MI]
Common Name English
ACETAMIDOBENZENE
Systematic Name English
PHENALGENE
Common Name English
ACETYLAMINOBENZENE
Systematic Name English
ACETANILIDE [VANDF]
Common Name English
ACETANILIDUM [HPUS]
Common Name English
ACETAMIDE, N-PHENYL-
Systematic Name English
ANTIFEBRIN
Common Name English
ACETANILIDUM
HPUS  
Common Name English
ACETAMINOPHEN RELATED COMPOUND D [USP IMPURITY]
Common Name English
NSC-7636
Code English
ANTIFEBRINUM
Common Name English
Code System Code Type Description
MESH
C508827
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
CONCEPT Industrial Aid
PUBCHEM
904
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-150-7
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
DAILYMED
SP86R356CC
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
RS_ITEM_NUM
1004001
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
ALTERNATIVE
EVMPD
SUB12710MIG
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
SMS_ID
100000077947
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
NSC
203231
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID2022543
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
ChEMBL
CHEMBL269644
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
CAS
103-84-4
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
RS_ITEM_NUM
1003042
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
NCI_THESAURUS
C76696
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
MERCK INDEX
m1319
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY Merck Index
FDA UNII
SP86R356CC
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
CHEBI
28884
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
WIKIPEDIA
ACETANILIDE
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
RXCUI
162
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
54
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
HSDB
2665
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
NSC
7636
Created by admin on Mon Mar 31 17:55:32 GMT 2025 , Edited by admin on Mon Mar 31 17:55:32 GMT 2025
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Metabolite to parent drug I non-uraemic human plasma 0.9-1.6
METABOLITE TO PARENT DRUG RATIO
PLASMA
PARENT -> METABOLITE
METABOLITE ACTIVE -> PARENT
Percent of dose excreted in urine as metabolite 60-80
URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY