| 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=CC(O)=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)
| Molecular Formula | C8H9NO2 |
| Molecular Weight | 151.1626 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
CNS Activity
Approval Year
Sample Use Guides
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.
