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QuickView for Atovaquone (compound)

Name: Atovaquone
PubChem Compound ID: 74989
Description: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.
Molecular formula: C22H19ClO3
Molecular weight: 366.837 g/mol
1,4-Naphthalenedione, 2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-; Malarone Pediatric; CRL-8131 & Atovaquone; SPBio_001849; 2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone; Spectrum2_001665; LS-178256; 2-[trans-4-(p-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone; KBio1_001726; KBio3_001901.
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Name: Atovaquone
Name (isomeric): DB01117
Drug Type: small molecule
Description: A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.
Brand: Malarone, Malarone Pediatric
Brand name mixture: Malarone Pediatric(Atovaquone + Proguanil Hydrochloride), Malarone(Atovaquone + Proguanil Hydrochloride)
Category: Antimalarials, Anti-Infective Agents, Antiprotozoal Agents, Antifungal Agents, Enzyme Inhibitors
CAS number: 95233-18-4
Indication: For the treatment or prevention of <i>Pneumocystis carinii</i> pneumonia in patients who are intolerant to trimethoprim-sulfamethoxazole (TMP-SMX). Also indicated for the acute oral treatment of mild to moderate PCP in patients who are intolerant to TMP-SMX.
Atovaquone is a highly lipophilic drug that closely resembles the structure ubiquinone. Its inhibitory effect being comparable to ubiquinone, in sensitive parasites atovaquone can act by selectively affecting mitochondrial electron transport and parallel processes such as ATP and pyrimidine biosynthesis. For illustration, cytochrome bc1 complex (co...
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Mechanism of Action:
Atovaquone is a hydroxy- 1, 4- naphthoquinone, an analog of ubiquinone, with antipneumocystis activity. The mechanism of action against Pneumocystis carinii has not been fully elucidated. In Plasmodium species, the site of action appears to be the cytochrome bc1 complex (Complex III). Several metabolic enzymes are linked to the mitochondrial...
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Absorption: The bioavailability of atovaquone is low and variable and is highly dependent on formulation and diet. Bioavailability of the suspension increases two-fold when administered with meals. When administered with food, bioavailability is approximately 47%. Without food, the bioavailability is 23%.
Protein binding: Atovaquone is extensively bound to plasma proteins (99.9%) over the concentration range of 1 to 90 µg/mL.
Biotransformation: Some evidence suggests limited metabolism (although no metabolites have been identified).
Route of elimination: The half-life of atovaquone is long due to presumed enterohepatic cycling and eventual fecal elimination. There was little or no excretion of atovaquone in the urine (less than 0.6%).
Half Life: 2.2 to 3.2 days
Clearance: 10.4 +/- 5.5 ml/min [HIV-infected patients receiving IV administration]
Toxicity: The median lethal dose is higher than the maximum oral dose tested in mice and rats (1825 mg/kg per day). Overdoses up to 31,500 mg of atovaquone have been reported. In one such patient who also took an unspecified dose of dapsone, methemoglobinemia occurred. Rash has also been reported after overdose.
Affected organisms: Plasmodium
Food interaction:
Fatty foods increase absorption.
Take with food, bioavailability is increased 2 to 3 fold.
Drug interaction:
RifabutinRifabutin decreases the effect of atovaquone
TetracyclineTetracycline may decrease the effect of atovaquone.
ZidovudineAtovaquone increases the effect and toxicity of zidovudine
RifampinRifampin may decrease the effect of atovaquone.