| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H10O3 |
| Molecular Weight | 166.1739 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=CC=C1O)C(C)=O
InChI
InChIKey=DFYRUELUNQRZTB-UHFFFAOYSA-N
InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
Apocynin, also known as acetovanillone, is a natural organic compound related to vanillin. It has been isolated from a variety of plant sources. Metabolites of apocynin are able to block the activity of NADPH oxidase, thus giving apocynin antioxidant and anti-inflammatory capabilities. Effects of apocynin on the concentration of reactive oxygen and nitrogen species in patients with asthma and chronic obstructive pulmonary disease were investigated in phase I clinical trials. In preclinical models, it was found that apocynin provides neuroprotective effects in models of stroke and Parkinson's disease.
CNS Activity
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In a clinical trial against chronic obstructive pulmonary disease, effects of nebulized apocynin (0.5 mg/ml, 6 ml) were assessed in exhaled breath condensate. In rat models of Parkinson's disease, apocynin was administered intraperitoneally at 10 mg/kg. In a model of rheumatoid arthritis, apocynin was administered orally.
Route of Administration:
Other
The NADPH oxidase inhibitory activity of apocynin and products of its oxidation (AOP) was assessed in an endothelial cell-based assay by measuring the generation of •O2− via cytochrome c reduction. Apocynin itself possesses minimal inhibitory activity (IC50 > 1 mM), while the extracted water-soluble phase of its metabolites exhibited an apparent IC50 value of 155 nM.
SUBSTANCE RECORD
