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Details

Stereochemistry ACHIRAL
Molecular Formula C8H9NO
Molecular Weight 135.1635
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACETANILIDE

SMILES

CC(=Nc1ccccc1)O

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 135.1635
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
Cloning, sequence analysis, and characterization of the astA gene encoding an arylsulfate sulfotransferase from Citrobacter freundii.
2001 Aug
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
Experimental and theoretical microdialysis studies of in situ metabolism.
2001 Mar
Interventions for relieving the pain and discomfort of screening mammography.
2002
Perazine as a potent inhibitor of human CYP1A2 but not CYP3A4.
2002 Jul-Aug
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
Biological activity of p-methylaminophenol, an essential structural component of N-(4-hydroxyphenyl)retinamide, fenretinide.
2002 Nov
1H-NMR assay of papaverine hydrochloride and formulations.
2002 Nov-Dec
Novel chromatographic separation and carbon solid-phase extraction of acetanilide herbicide degradation products.
2002 Nov-Dec
Biodegradation of acetanilide herbicides acetochlor and butachlor in soil.
2002 Oct
The bis-barium complex of a butterfly crown ether as a phototunable supramolecular catalyst.
2003 Feb 26
The metabolism of 2-trifluormethylaniline and its acetanilide in the rat by 19F NMR monitored enzyme hydrolysis and 1H/19F HPLC-NMR spectroscopy.
2003 Jan 1
The mandelamide keto-enol system in aqueous solution. Generation of the enol by hydration of phenylcarbamoylcarbene.
2003 Jan 8
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
Characterization of a strain of Sphingobacterium sp. and its degradation to herbicide mefenacet.
2004
The effect of carbon surface chemical composition on the adsorption of acetanilide.
2004 Apr 1
[Acetaminophen].
2004 Dec
The synthesis and anticonvulsant activity of some omega-phthalimido-N-phenylacetamide and propionamide derivatives.
2004 Feb
High-performance liquid chromatographic-nuclear magnetic resonance investigation of the isomerization of alachlor-ethanesulfonic acid.
2004 Jan 2
Molecular properties and intermolecular forces--factors balancing the effect of carbon surface chemistry in adsorption of organics from dilute aqueous solutions.
2004 Jul 1
Synthesis and structure/NMDA receptor affinity relationships of 1-substituted tetrahydro-3-benzazepines.
2004 Mar 15
Design of N-acetyl-6-sulfo-beta-d-glucosaminide-based inhibitors of influenza virus sialidase.
2004 Mar 15
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
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
Kinetic analysis of maize glutathione S-transferase I catalysing the detoxification from chloroacetanilide herbicides.
2005 Sep
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 Sat Jun 26 13:02:22 UTC 2021
Edited
by admin
on Sat Jun 26 13:02:22 UTC 2021
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 [WHO-DD]
Common Name English
ACETANILIDE [MART.]
Common Name English
ACETANILID
INCI  
INCI  
Official Name English
ACETANILID [INCI]
Common Name English
NSC-203231
Code English
ACETAMINOPHEN RELATED COMPOUND D [USP]
Common Name English
ACETANILIDE [HSDB]
Common Name English
N-PHENYLACETAMIDE
Systematic Name English
ACETAMINOPHEN RELATED COMPOUND D [USP-RS]
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
PARACETAMOL IMPURITY D [EP]
Common Name English
ACETAMIDE, N-PHENYL-
Systematic Name English
ANTIFEBRIN
Common Name English
ACETANILIDUM
HPUS  
Common Name English
NSC-7636
Code English
ANTIFEBRINUM
Common Name English
Code System Code Type Description
MESH
C508827
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
CONCEPT Industrial Aid
PUBCHEM
904
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
USP_CATALOG
1004001
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
203-150-7
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
EVMPD
SUB12710MIG
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
EPA CompTox
103-84-4
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL269644
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
CAS
103-84-4
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
NCI_THESAURUS
C76696
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
MERCK INDEX
M1319
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY Merck Index
FDA UNII
SP86R356CC
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
USP_CATALOG
1003042
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
ACETANILIDE
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
RXCUI
162
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
54
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
PRIMARY
HSDB
2665
Created by admin on Sat Jun 26 13:02:22 UTC 2021 , Edited by admin on Sat Jun 26 13:02:22 UTC 2021
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