U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 mg/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
n = 1
Health Status: unhealthy
Age Group: 45 years
Sex: F
Population Size: 1
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
Co-administed with::
phenazone(0.26 g; oral; 3/day)
caffeine(0.13 g; oral; 3/day)
Sources:
unhealthy, 55 years
n = 1
Health Status: unhealthy
Condition: headache
Age Group: 55 years
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: adult
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 45 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 45 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 45 years
Sex: F
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 45 years
Sex: F
Population Size: 1
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
Co-administed with::
phenazone(0.26 g; oral; 3/day)
caffeine(0.13 g; oral; 3/day)
Sources:
unhealthy, 55 years
n = 1
Health Status: unhealthy
Condition: headache
Age Group: 55 years
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: adult
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: adult
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: adult
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: adult
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: adult
Sex: F
Population Size: 1
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
The utilization of aniline, chlorinated aniline, and aniline blue as the only source of nitrogen by fungi in water.
2001 Apr
Acyl substitution at the ortho position of anilides enhances oral bioavailability of thiophene sulfonamides: TBC3214, an ETA selective endothelin antagonist.
2001 Apr 12
Cloning, sequence analysis, and characterization of the astA gene encoding an arylsulfate sulfotransferase from Citrobacter freundii.
2001 Aug
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
Synthesis of tricyclic indole-2-carboxylic [correction of caboxylic] acids as potent NMDA-glycine antagonists.
2001 May 18
Nonlinear free energy relationship in the general-acid-catalyzed acylation of rat kidney gamma-glutamyl transpeptidase by a series of gamma-glutamyl anilide substrate analogues.
2001 Oct 23
Liquid chromatographic resolution of N-acyl-alpha-amino acids as their anilide derivatives on a chiral stationary phase based on (S)-leucine.
2002 Jun
Determination of crude protein in animal feed, forage, grain, and oilseeds by using block digestion with a copper catalyst and steam distillation into boric acid: collaborative study.
2002 Mar-Apr
Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate).
2002 Oct 18
Application of the PKCYP test to predict caffeine clearance mediated by CYP1A2 in a rat acute liver injury model.
2003
Contribution of human cytochrome p-450 isoforms to the metabolism of the simplest phenothiazine neuroleptic promazine.
2003 Apr
[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
The bis-barium complex of a butterfly crown ether as a phototunable supramolecular catalyst.
2003 Feb 26
Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli.
2003 Jul 30
Distinct thermodynamics for the formation and cleavage of N-H bonds in aniline and ammonia. Directly-observed reductive elimination of ammonia from an isolated amido hydride complex.
2003 Nov 12
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
Antipyretic therapy.
2004 Jan 1
[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
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
Kinetic analysis of maize glutathione S-transferase I catalysing the detoxification from chloroacetanilide herbicides.
2005 Sep
Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines.
2005 Sep 7
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 Fri Dec 15 15:22:26 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:26 GMT 2023
Record UNII
SP86R356CC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETANILIDE
HSDB   MART.   MI   VANDF   WHO-DD  
Systematic Name English
ACETANILIDE [USP-RS]
Common Name English
ACETANILIDE MELTING POINT STANDARD
USP-RS  
Common Name English
ACETANILIDE [MART.]
Common Name English
ACETANILID
INCI  
INCI  
Official Name English
Acetanilide [WHO-DD]
Common Name English
ACETANILID [INCI]
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 Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
CONCEPT Industrial Aid
PUBCHEM
904
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-150-7
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
DAILYMED
SP86R356CC
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
RS_ITEM_NUM
1004001
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
ALTERNATIVE
EVMPD
SUB12710MIG
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
SMS_ID
100000077947
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
NSC
203231
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID2022543
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
ChEMBL
CHEMBL269644
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
CAS
103-84-4
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
RS_ITEM_NUM
1003042
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
NCI_THESAURUS
C76696
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
MERCK INDEX
m1319
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY Merck Index
FDA UNII
SP86R356CC
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
CHEBI
28884
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
WIKIPEDIA
ACETANILIDE
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
RXCUI
162
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
54
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
HSDB
2665
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
PRIMARY
NSC
7636
Created by admin on Fri Dec 15 15:22:26 GMT 2023 , Edited by admin on Fri Dec 15 15:22:26 GMT 2023
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