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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
Acyl substitution at the ortho position of anilides enhances oral bioavailability of thiophene sulfonamides: TBC3214, an ETA selective endothelin antagonist.
2001 Apr 12
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
Immune thrombocytopenia resulting from sensitivity to metabolites of naproxen and acetaminophen.
2001 Jun 15
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
Synthesis of tricyclic indole-2-carboxylic [correction of caboxylic] acids as potent NMDA-glycine antagonists.
2001 May 18
[Various mechanisms of the depriming effect of bacterial endotoxin on drug metabolism].
2001 Sep-Oct
Effect of alachlor on hepatic cytochrome P450 enzymes in rats.
2002 Feb
Femtosecond study of self-trapped vibrational excitons in crystalline acetanilide.
2002 Feb 11
Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.
2002 Feb 27
Influence of herbicide structure, clay acidity, and humic acid coating on acetanilide herbicide adsorption on homoionic clays.
2002 Jul 3
Perazine as a potent inhibitor of human CYP1A2 but not CYP3A4.
2002 Jul-Aug
Liquid chromatographic resolution of N-acyl-alpha-amino acids as their anilide derivatives on a chiral stationary phase based on (S)-leucine.
2002 Jun
Iodine(V) reagents in organic synthesis. Part 3. New routes to heterocyclic compounds via o-iodoxybenzoic acid-mediated cyclizations: generality, scope, and mechanism.
2002 Mar 13
Biological activity of p-methylaminophenol, an essential structural component of N-(4-hydroxyphenyl)retinamide, fenretinide.
2002 Nov
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
Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate).
2002 Oct 18
Purification and characterization of rat pancreatic fatty acid ethyl ester synthase and its structural and functional relationship to pancreatic cholesterol esterase.
2003
Reactions of the ionized enol tautomer of acetanilide: elimination of HNCO via a novel rearrangement.
2003
Contribution of human cytochrome p-450 isoforms to the metabolism of the simplest phenothiazine neuroleptic promazine.
2003 Apr
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
Metabolites of a blocked chloramphenicol producer.
2003 Jan
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
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
Unmasking tandem site interaction in human acetylcholinesterase. Substrate activation with a cationic acetanilide substrate.
2003 May 13
Ethyl N-phenyloxamate.
2003 Oct
The effect of carbon surface chemical composition on the adsorption of acetanilide.
2004 Apr 1
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
Design of N-acetyl-6-sulfo-beta-d-glucosaminide-based inhibitors of influenza virus sialidase.
2004 Mar 15
[Salicylanilides: still a potential antibacterially active group].
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
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
Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines.
2005 Sep 7
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