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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

atovaquone is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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-
InChI Key KUCQYCKVKVOKAY-CTYIDZIISA-N
References
1. Boggild AK, Parise ME, Lewis LS, Kain KC. (2007)
Atovaquone-proguanil: report from the CDC expert meeting on malaria chemoprophylaxis (II).
Am J Trop Med Hyg, 76 (2): 208-23. [PMID:17297027]
2. Canfield CJ, Pudney M, Gutteridge WE. (1995)
Interactions of atovaquone with other antimalarial drugs against Plasmodium falciparum in vitro.
Exp Parasitol, 80 (3): 373-81. [PMID:7729473]
3. Delves M, Plouffe D, Scheurer C, Meister S, Wittlin S, Winzeler EA, Sinden RE, Leroy D. (2012)
The activities of current antimalarial drugs on the life cycle stages of Plasmodium: a comparative study with human and rodent parasites.
PLoS Med, 9 (2): e1001169. [PMID:22363211]
4. Fisher N, Abd Majid R, Antoine T, Al-Helal M, Warman AJ, Johnson DJ, Lawrenson AS, Ranson H, O'Neill PM, Ward SA et al.. (2012)
Cytochrome b mutation Y268S conferring atovaquone resistance phenotype in malaria parasite results in reduced parasite bc1 catalytic turnover and protein expression.
J Biol Chem, 287 (13): 9731-41. [PMID:22282497]
5. Hughes W, Leoung G, Kramer F, Bozzette SA, Safrin S, Frame P, Clumeck N, Masur H, Lancaster D, Chan C et al.. (1993)
Comparison of atovaquone (566C80) with trimethoprim-sulfamethoxazole to treat Pneumocystis carinii pneumonia in patients with AIDS.
N Engl J Med, 328 (21): 1521-7. [PMID:8479489]
6. Krause PJ, Lepore T, Sikand VK, Gadbaw Jr J, Burke G, Telford 3rd SR, Brassard P, Pearl D, Azlanzadeh J, Christianson D et al.. (2000)
Atovaquone and azithromycin for the treatment of babesiosis.
N Engl J Med, 343 (20): 1454-8. [PMID:11078770]
7. Looareesuwan S, Viravan C, Webster HK, Kyle DE, Hutchinson DB, Canfield CJ. (1996)
Clinical studies of atovaquone, alone or in combination with other antimalarial drugs, for treatment of acute uncomplicated malaria in Thailand.
Am J Trop Med Hyg, 54 (1): 62-6. [PMID:8651372]
8. Painter HJ, Morrisey JM, Mather MW, Vaidya AB. (2007)
Specific role of mitochondrial electron transport in blood-stage Plasmodium falciparum.
Nature, 446 (7131): 88-91. [PMID:17330044]
9. Srivastava IK, Rottenberg H, Vaidya AB. (1997)
Atovaquone, a broad spectrum antiparasitic drug, collapses mitochondrial membrane potential in a malarial parasite.
J Biol Chem, 272 (7): 3961-6. [PMID:9020100]
10. Vaidya AB, Lashgari MS, Pologe LG, Morrisey J. (1993)
Structural features of Plasmodium cytochrome b that may underlie susceptibility to 8-aminoquinolines and hydroxynaphthoquinones.
Mol Biochem Parasitol, 58 (1): 33-42. [PMID:8459834]