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)
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 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
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 n = 1 Health Status: unhealthy Age Group: 45 years Sex: F Population Size: 1 Sources: |
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 Co-administed with:: phenazone(0.26 g; oral; 3/day) Sources: caffeine(0.13 g; oral; 3/day) |
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 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 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) Sources: caffeine(0.13 g; oral; 3/day) |
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
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 |
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Application of the PKCYP test to predict caffeine clearance mediated by CYP1A2 in a rat acute liver injury model. | 2003 |
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Purification and characterization of rat pancreatic fatty acid ethyl ester synthase and its structural and functional relationship to pancreatic cholesterol esterase. | 2003 |
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[Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital]. | 2003 Aug |
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Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli. | 2003 Jul 30 |
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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 |
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Ethyl N-phenyloxamate. | 2003 Oct |
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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 |
|
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 |
|
[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
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Code System | Code | Type | Description | ||
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C508827
Created by
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C45678
Created by
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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
Created by
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ALTERNATIVE | |||
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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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1003042
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C76696
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m1319
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PRIMARY | Merck Index | ||
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SP86R356CC
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28884
Created by
admin on Fri Dec 15 15:22:26 UTC 2023 , Edited by admin on Fri Dec 15 15:22:26 UTC 2023
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ACETANILIDE
Created by
admin on Fri Dec 15 15:22:26 UTC 2023 , Edited by admin on Fri Dec 15 15:22:26 UTC 2023
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162
Created by
admin on Fri Dec 15 15:22:26 UTC 2023 , Edited by admin on Fri Dec 15 15:22:26 UTC 2023
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PRIMARY | RxNorm | ||
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54
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2665
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7636
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
PARENT (METABOLITE)