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Details

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

Description

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Application of the PKCYP test to predict caffeine clearance mediated by CYP1A2 in a rat acute liver injury model.
2003
Purification and characterization of rat pancreatic fatty acid ethyl ester synthase and its structural and functional relationship to pancreatic cholesterol esterase.
2003
[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital].
2003 Aug
Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli.
2003 Jul 30
Novel hydroxamate and anilide derivatives as potent histone deacetylase inhibitors: synthesis and antiproliferative evaluation.
2003 Nov
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
Ethyl N-phenyloxamate.
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
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
The synthesis and anticonvulsant activity of some omega-phthalimido-N-phenylacetamide and propionamide derivatives.
2004 Feb
Dissipation of alachlor in cotton plant, soil and water and its bioaccumulation in fish.
2004 Feb
Quantitative determination of p-aminosalicylic acid and its degradation product m-aminophenol in pellets by ion-pair high-performance liquid chromatography applying the monolithic Chromolith Speedrod RP-18e column.
2004 Jan
The olivacine derivative s 16020 (9-hydroxy-5,6-dimethyl-N-[2-(dimethylamino)ethyl)-6H-pyrido(4,3-B)-carbazole-1-carboxamide) induces CYP1A and its own metabolism in human hepatocytes in primary culture.
2004 Jan
Antipyretic therapy.
2004 Jan 1
Evaluation of toxic equivalency factors for induction of cytochromes P450 CYP1A1 and CYP1A2 enzyme activity by dioxin-like compounds.
2004 Jan 15
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
Molecular properties and intermolecular forces--factors balancing the effect of carbon surface chemistry in adsorption of organics from dilute aqueous solutions.
2004 Jul 1
Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides.
2004 Jun
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
[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
Flutolanil and carboxin resistance in Coprinus cinereus conferred by a mutation in the cytochrome b560 subunit of succinate dehydrogenase complex (Complex II).
2004 Oct
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
Inhibition of human and rat CYP1A2 by TCDD and dioxin-like chemicals.
2005 Apr
Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts.
2005 Apr 1
Multiple mechanisms are involved in the biliary excretion of acetaminophen sulfate in the rat: role of Mrp2 and Bcrp1.
2005 Aug
Behavior of acetanilide herbicides in soils and the possibility of groundwater contamination.
2005 Dec
Removal of neutral chloroacetamide herbicide degradates during simulated unit processes for drinking water treatment.
2005 Dec
A dual-electrode approach for highly selective detection of glucose based on diffusion layer theory: experiments and simulation.
2005 Feb 4
Kinetic stability of heteroleptic (beta-diketiminato) heavier alkaline-earth (Ca, Sr, Ba) amides.
2005 Jan 21
Studies on the reactions between daptomycin and glyceraldehyde.
2005 Jan 31
Thermodynamic study of the transfer of acetanilide and phenacetin from water to different organic solvents.
2005 Jun
Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease.
2005 Jun 30
Anion-assisted trans-cis isomerization of palladium(II) phosphine complexes containing acetanilide functionalities through hydrogen bonding interactions.
2005 Mar 28
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
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
Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines.
2005 Sep 7
[Synthesis of two new acetanilide derivatives and their effect on the serum antioxidant vitamins (A, E, and C) and the MDA level in rats].
2005 Sep-Oct
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
Establishing a chromium-reactor design for measuring delta2H values of solid polyhalogenated compounds using direct elemental analysis and stable isotope ratio mass spectrometry.
2006 Jan
Patents
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:06:55 UTC 2019
Edited
by admin
on Mon Oct 21 21:06:55 UTC 2019
Record UNII
SP86R356CC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACETANILIDE
HSDB   MART.   MI   VANDF   WHO-DD  
Systematic 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 MELTING POINT STANDARD [USP-RS]
Common Name English
ACETANILIDE [HSDB]
Common Name English
N-PHENYLACETAMIDE
Systematic 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 Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
CONCEPT Industrial Aid
PUBCHEM
904
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
ECHA (EC/EINECS)
203-150-7
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
EVMPD
SUB12710MIG
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
EPA CompTox
103-84-4
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
ChEMBL
CHEMBL269644
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
CAS
103-84-4
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
NCI_THESAURUS
C76696
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
MERCK INDEX
M1319
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
ACETANILIDE
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY
RXCUI
162
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
PRIMARY RxNorm
HSDB
103-84-4
Created by admin on Mon Oct 21 21:06:55 UTC 2019 , Edited by admin on Mon Oct 21 21:06:55 UTC 2019
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