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
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)
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 |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.seidlerchem.com/acetanilide.htm
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.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
90% |
ACETANILIDE plasma | Homo sapiens |
Doses
Dose | Population | Adverse 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 |
Other AEs: Gasping, Blurred vision... Other AEs: Gasping Sources: Blurred vision Cyanosis Cardio-respiratory distress |
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 |
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 |
Other AEs: Vertigo, Tinnitus... Other AEs: Vertigo Sources: Tinnitus Temporal arteritis Headache dull Weakness |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/1989524/ Page: 1.0 |
major |
PubMed
Title | Date | PubMed |
---|---|---|
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
Substance Class |
Chemical
Created
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admin
on
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Mon Mar 31 17:55:32 GMT 2025
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Record UNII |
SP86R356CC
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Validated (UNII)
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C508827
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C45678
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CONCEPT | Industrial Aid | ||
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904
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203-150-7
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SP86R356CC
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1004001
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SUB12710MIG
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100000077947
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203231
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DTXSID2022543
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CHEMBL269644
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103-84-4
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C76696
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m1319
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SP86R356CC
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28884
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ACETANILIDE
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162
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54
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
Metabolite to parent drug I non-uraemic human plasma 0.9-1.6
METABOLITE TO PARENT DRUG RATIO
PLASMA
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PARENT -> METABOLITE |
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METABOLITE ACTIVE -> PARENT |
Percent of dose excreted in urine as metabolite 60-80
URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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