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 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 |
|---|---|---|
| Isolation of a bacterium that degrades urethane compounds and characterization of its urethane hydrolase. | 2006-04 |
|
| Discovery of novel and potent thiazoloquinazolines as selective Aurora A and B kinase inhibitors. | 2006-02-09 |
|
| Establishing a chromium-reactor design for measuring delta2H values of solid polyhalogenated compounds using direct elemental analysis and stable isotope ratio mass spectrometry. | 2006-01 |
|
| Behavior of acetanilide herbicides in soils and the possibility of groundwater contamination. | 2005-12 |
|
| Removal of neutral chloroacetamide herbicide degradates during simulated unit processes for drinking water treatment. | 2005-12 |
|
| [Synthesis of two new acetanilide derivatives and their effect on the serum antioxidant vitamins (A, E, and C) and the MDA level in rats]. | 2005-10-26 |
|
| Safety of the methylene blue plus chloroquine combination in the treatment of uncomplicated falciparum malaria in young children of Burkina Faso [ISRCTN27290841]. | 2005-09-22 |
|
| Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines. | 2005-09-07 |
|
| Kinetic analysis of maize glutathione S-transferase I catalysing the detoxification from chloroacetanilide herbicides. | 2005-09 |
|
| Multiple mechanisms are involved in the biliary excretion of acetaminophen sulfate in the rat: role of Mrp2 and Bcrp1. | 2005-08 |
|
| Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease. | 2005-06-30 |
|
| Thermodynamic study of the transfer of acetanilide and phenacetin from water to different organic solvents. | 2005-06 |
|
| [Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats]. | 2005-05-25 |
|
| 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. | 2005-05-13 |
|
| Synthesis of aryl sulfones via L-proline-promoted CuI-catalyzed coupling reaction of aryl halides with sulfinic acid salts. | 2005-04-01 |
|
| Inhibition of human and rat CYP1A2 by TCDD and dioxin-like chemicals. | 2005-04 |
|
| Anion-assisted trans-cis isomerization of palladium(II) phosphine complexes containing acetanilide functionalities through hydrogen bonding interactions. | 2005-03-28 |
|
| A dual-electrode approach for highly selective detection of glucose based on diffusion layer theory: experiments and simulation. | 2005-02-04 |
|
| Studies on the reactions between daptomycin and glyceraldehyde. | 2005-01-31 |
|
| Kinetic stability of heteroleptic (beta-diketiminato) heavier alkaline-earth (Ca, Sr, Ba) amides. | 2005-01-21 |
|
| [Acetaminophen]. | 2004-12 |
|
| Synthesis and biological evaluation of 1-aryl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one inhibitors of cyclin-dependent kinases. | 2004-11-18 |
|
| [Salicylanilides: still a potential antibacterially active group]. | 2004-11 |
|
| High-performance liquid chromatographic method for simultaneous determination of sophoridine and matrine in rat plasma. | 2004-11 |
|
| Controlling the conformation of arylamides: computational studies of intramolecular hydrogen bonds between amides and ethers or thioethers. | 2004-10-11 |
|
| Flutolanil and carboxin resistance in Coprinus cinereus conferred by a mutation in the cytochrome b560 subunit of succinate dehydrogenase complex (Complex II). | 2004-10 |
|
| Nucleophilic aromatic substitution on aryl-amido ligands promoted by oxidizing osmium(IV) centers. | 2004-09-20 |
|
| Molecular properties and intermolecular forces--factors balancing the effect of carbon surface chemistry in adsorption of organics from dilute aqueous solutions. | 2004-07-01 |
|
| Orally active CCR5 antagonists as anti-HIV-1 agents 2: synthesis and biological activities of anilide derivatives containing a pyridine N-oxide moiety. | 2004-07 |
|
| Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides. | 2004-06 |
|
| Bioisosteric replacement of anilide with benzoxazole: potent and orally bioavailable antagonists of VLA-4. | 2004-05-03 |
|
| Hydrogen-bonded polymer gel and its application as a temperature-sensitive drug delivery system. | 2004-05 |
|
| Energy of charged states in the acetanilide crystal: trapping of charge-transfer states at vacancies as a possible mechanism for optical damage. | 2004-04-15 |
|
| The effect of carbon surface chemical composition on the adsorption of acetanilide. | 2004-04-01 |
|
| Synthesis and structure/NMDA receptor affinity relationships of 1-substituted tetrahydro-3-benzazepines. | 2004-03-15 |
|
| Design of N-acetyl-6-sulfo-beta-d-glucosaminide-based inhibitors of influenza virus sialidase. | 2004-03-15 |
|
| The synthesis and anticonvulsant activity of some omega-phthalimido-N-phenylacetamide and propionamide derivatives. | 2004-02 |
|
| Dissipation of alachlor in cotton plant, soil and water and its bioaccumulation in fish. | 2004-02 |
|
| Evaluation of toxic equivalency factors for induction of cytochromes P450 CYP1A1 and CYP1A2 enzyme activity by dioxin-like compounds. | 2004-01-15 |
|
| High-performance liquid chromatographic-nuclear magnetic resonance investigation of the isomerization of alachlor-ethanesulfonic acid. | 2004-01-02 |
|
| Antipyretic therapy. | 2004-01-01 |
|
| 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. | 2004-01 |
|
| 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. | 2004-01 |
|
| Characterization of a strain of Sphingobacterium sp. and its degradation to herbicide mefenacet. | 2004 |
|
| 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. | 2003-11-12 |
|
| Ethyl N-phenyloxamate. | 2003-10 |
|
| [Surveillance on concurrent administration of quinolones and anti-inflammatory drugs in a community hospital]. | 2003-08 |
|
| Colorimetric reversibility of polydiacetylene supramolecules having enhanced hydrogen-bonding under thermal and pH stimuli. | 2003-07-30 |
|
| 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 |
Patents
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| Code System | Code | Type | Description | ||
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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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1003042
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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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2665
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7636
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
PARENT (METABOLITE)