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Atovaquone is a naphthalene analogue.Atovaquone is hydroxy-1,4-naphthoquinone, a ubiquinone analogue with antipneumocystis activity.
Atovaquone is an antiprotozoal mitochondrial electron transfer inhibitor, antimalarial, antipneumocystis, and is also used in the treatment of toxoplasmosis. It acts by interacting with Rieske iron-sulphur protein and cytochrome b in the ubiquinone oxidation pocket, inhibiting the cytochrome bc(1) complex.
Pharmacological Effect of Atovaquone.
Atovaquone is a hydroxy 1,4-naphthoquinoline, a homologue of coenzyme Q, with activity against several protozoa. Against the genus Plasmodium, the site of action is the cytochrome bcl binding site (binding site III). It reversibly binds to the 11,500 Da molecular motif on the peptide.
Dihydroorotic acid dehydrogenase is an important enzyme in the biosynthesis of pyridine, linking mitochondria for electron transfer via coenzyme Q. Therefore, this product prevents the synthesis of pyridine by inhibiting electron transfer. Therefore, it prevents pyridine synthesis by inhibiting electron transfer.
A number of metabolic enzymes are involved in mitochondrial electron transport via coenzyme Q. Therefore, the inhibition of electron transport by this product actually inhibits the activity of these enzymes.
The 100 mg/kg-d dose of this product prevents and treats 100% of P. carinii in mice.The IC50 for inhibition ranges from 0.1 to 3.0 μg/ml.
Drug interactions of Atovaquone.
1, due to the high protein binding rate of this product, if combined with another drug with high binding rate and narrow therapeutic window, the phenomenon of competition for binding sites will occur.
2、Combining this product with rifampicin will cause a significant decrease in the blood concentration of the former, and rifabutin also has the same effect.
3, Tetracycline or metoclopramide can reduce the blood concentration of this product.
Product methods of Bulk Atovaquone Powder.
Friedd-Crafts acylation of cyclohexene with acetyl chloride in the presence of aluminium trichloride yielded 4-(4-chlorophenyl)cyclohexylmethyl ketone (I) by reaction of the orange intermediate with benzene chloride. Its oxidation with bromine in sodium hydroxide aqueous tide night gave 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid (II). It was reacted with 2-chloro-1,4-naphthoquinone in the presence of nitric acid forging, and the resulting product was hydrolysed in methanol, and aqueous sodium hydroxide refluxed to give atovaquone.
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