atovaquone   Click here for help

GtoPdb Ligand ID: 9695

Synonyms: 566C80 | Mepron® | Wellvone®
Approved drug PDB Ligand Antimalarial Ligand
atovaquone is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with proguanil.
Note that we have drawn the molecule as specified by the INN record and ChEMBL entry listed on this summary page. The structure for PubChem CID 74989 (link in table below) is shown without specified stereochemistry (InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 54.37
Molecular weight 366.1
XLogP 6.31
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc(cc1)C1CCC(CC1)C1=C(O)C(=O)c2c(C1=O)cccc2
Isomeric SMILES Clc1ccc(cc1)[C@@H]1CC[C@H](CC1)C1=C(O)C(=O)c2c(C1=O)cccc2
InChI InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-
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Summary of Clinical Use Click here for help
Atovaquone is used in combination with proguanil in both the treatment of uncomplicated malaria caused by P. falciparum and in malaria prophylaxis [1-2]. The use of atovaquone as an antimalarial monotherapy is not indicated because of concerns regarding recrudescence rates and parasite resistance [7].
Other uses of atovaquone are as a combined therapy with azithromycin for the treatment of babesiosis [6] and as a monotherapy for the prevention and treatment of mild-to moderate pneumonia caused by P. jirovecii (PCP) in individuals who are sensitive to trimethoprim-sulfamethoazole treatment [5].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The mechanism of action of atovaquone has been studied most extensively in the Plasmodium parasite. The compound inhibits the cytochrome bc1 complex of the mitochondrial electron-transfer chain, with a subsequent collapse of the mitochondrial membrane potential [9-10]. An active cytochrome bc1 complex is necessary for the biosynthesis of pyrimidines and disruption of this pathway is lethal to the parasite [8].
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