Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H9NO2 |
| Molecular Weight | 151.1626 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)NC1=CC(O)=CC=C1
InChI
InChIKey=QLNWXBAGRTUKKI-UHFFFAOYSA-N
InChI=1S/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10)
Metacetamol (3-hydroxyacetanilide) is a structural isomer of the widely used drug paracetamol and is being considered as a promising alternative to the latter because of its lower toxicity. 3-hydroxyacetanilide, the positional isomer of
paracetamol, does not cause depletion of GSH in vivo
or hepatotoxicity even though the
extent of covalent binding of the reactive metabolite
(in vivo or in vitro) is comparable to that for an
equimolar dose of paracetamol. Metacetamol should prove to be a useful tool to aid in the discrimination of hepatic acetaminophen protein adducts that may be critical or noncritical to survival of hepatocytes
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Identification of hepatic protein targets of the reactive metabolites of the non-hepatotoxic regioisomer of acetaminophen, 3'-hydroxyacetanilide, in the mouse in vivo using two-dimensional gel electrophoresis and mass spectrometry. | 2001 |
|
| Enhanced acetaminophen hepatotoxicity in transgenic mice overexpressing BCL-2. | 2001 Nov |
|
| Cell culture model for acetaminophen-induced hepatocyte death in vivo. | 2002 Aug 1 |
|
| Enzymatic synthesis of 3'-hydroxyacetaminophen catalyzed by tyrosinase. | 2003 Nov-Dec |
|
| Application of stable isotope labeled glutathione and rapid scanning mass spectrometers in detecting and characterizing reactive metabolites. | 2005 |
|
| Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. | 2005 Dec |
|
| The reactive metabolite target protein database (TPDB)--a web-accessible resource. | 2007 Mar 16 |
|
| Multicenter study of acetaminophen hepatotoxicity reveals the importance of biological endpoints in genomic analyses. | 2007 Sep |
|
| Development of an HPLC-MS/MS method for the selective determination of paracetamol metabolites in mouse urine. | 2008 Mar 1 |
|
| Differential gene expression analysis of a known hepatotoxin, N-acetyl-p-amino-phenol (APAP) as compared to its non-toxic analog, N-acetyl-m-amino-phenol (AMAP) in mouse liver. | 2008 May |
|
| Bioinformatic analysis of xenobiotic reactive metabolite target proteins and their interacting partners. | 2009 Jun 12 |
|
| Differential regulation of mitogen-activated protein kinase pathways by acetaminophen and its nonhepatotoxic regioisomer 3'-hydroxyacetanilide in TAMH cells. | 2010 Jul |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Toxicity of meta or Metacetamol (3-hydroxyacetanilide) was evaluated in mice. The LD50 was 1025 mg/kg when given intraperitoneally (i.p.). The drug in doses greater than 400 mg/kg i.p. caused significant sedation. 3-Hydroxyacetanilide, 900 mg/kg i.p., did not cause hepatic necrosis evaluated by either histology or changes in plasma glutamate pyruvate transaminase activity.
The administration of acetyl-labeled [3H or 14C]3HAA (Metacetamol) (400 mg/kg, ip) produced levels of covalently bound radiolabel that were similar to those observed after an equimolar, hepatotoxic dose of [G-3H]acetaminophen.
Route of Administration:
Intraperitoneal
Metacetamol (3-hydroxyacetanilide), when incubated with liver
microsomes isolated from CS1 and DBA/2J mice,
co-factors and reduced glutathione (GSH) produced a dose-dependent depletion of GSH. 3-Hydroxyacetanilide (0.5 mM)
was a more potent depletor of GSH in vitro than was
paracetamol.
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NCI_THESAURUS |
C241
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621-42-1
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100000081191
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C81395
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CHEMBL9419
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3990
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Metacetamol
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ACTIVE MOIETY
