ATOVAQUONE

First approved in 1992

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H19ClO3
Molecular Weight	366.837
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C([C@H]2CC[C@@H](CC2)C3=CC=C(Cl)C=C3)C(=O)C4=CC=CC=C4C1=O

InChI

InChIKey=KUCQYCKVKVOKAY-CTYIDZIISA-N

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-

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020500s015lbl.pdf

Atovaquone is a chemical compound that belongs to the class of naphthoquinones; it is manufactured in the US in the liquid form, or oral suspension, under the brand name Mepron. Meron is used for the treatment or prevention of Pneumocystis carinii 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. The mechanism of action against Pneumocystis jiroveci 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 electron transport chain via ubiquinone. Inhibition of electron transport by atovaquone results in indirect inhibition of these enzymes. The ultimate metabolic effects of such blockade may include inhibition of nucleic acid and adenosine triphosphate (ATP) synthesis. Several laboratories, using different in vitro methodologies, have shown the IC50 (50% inhibitory concentration) of atovaquone against P. jiroveci to be 0.1 to 3.0 mcg/mL.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome b 2 Target ID: CHEMBL1777 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12791689	Inhibitor 8504
Dihydroorotate dehydrogenase (quinone), mitochondrial 3 Target ID: Q08210 Gene ID: 3885966.0 Gene Symbol: NA Target Organism: Plasmodium falciparum (isolate 3D7) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7726490	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pneumocystis jiroveci pneumonia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020500s015lbl.pdf	Curative		Approved 8583	MEPRON Approved Use 1.1 Prevention of Pneumocystis jiroveci Pneumonia. MEPRON® suspension is indicated for the prevention of Pneumocystis jiroveci pneumonia (PCP) in adults and adolescents (aged 13 years and older) who cannot tolerate trimethoprimsulfamethoxazole (TMP-SMX). 1.2 Treatment of Mild-to-Moderate Pneumocystis jiroveci Pneumonia MEPRON suspension is indicated for the acute oral treatment of mild-to-mod Launch Date 1992

C_max

Value	Dose	Analyte	Population
15.1 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
8.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
15.1 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED
15.3 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg 1 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED
16.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED
24 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg 2 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
324 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
801 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
280 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
169 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Analyte	Population
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FASTED
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg 1 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FED
0.1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	750 mg 2 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	ATOVAQUONE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1000 mg 2 times / day multiple, oral Highest studied dose Dose: 1000 mg, 2 times / day Route: oral Route: multiple Dose: 1000 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8851570	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/8851570	Sources: https://pubmed.ncbi.nlm.nih.gov/8851570
31500 mg single, oral Overdose Dose: 31500 mg Route: oral Route: single Dose: 31500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	Other AEs: Methemoglobinemia, Rash... Other AEs: Methemoglobinemia Rash Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	Disc. AE: Rash, Diarrhea... AEs leading to discontinuation/dose reduction: Rash (grade 1-2, 6%) Diarrhea (4%) Nausea (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	Disc. AE: Vomiting, ALT increased... AEs leading to discontinuation/dose reduction: Vomiting (<1%) ALT increased (2%) Aspartate aminotransferase increase (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	Disc. AE: Creatinine increased, Blood urea nitrogen increased... AEs leading to discontinuation/dose reduction: Creatinine increased (1%) Blood urea nitrogen increased (1%) Amylase increased (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf

AEs

AE	Significance	Dose	Population
Methemoglobinemia		31500 mg single, oral Overdose Dose: 31500 mg Route: oral Route: single Dose: 31500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Rash		31500 mg single, oral Overdose Dose: 31500 mg Route: oral Route: single Dose: 31500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Nausea	3% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Diarrhea	4% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Rash	grade 1-2, 6% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Rash	4% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
ALT increased	2% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Aspartate aminotransferase increase	2% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Vomiting	<1% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Amylase increased	1% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Blood urea nitrogen increased	1% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf
Creatinine increased	1% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 BCRP 910 BSEP 550 MRP1 116 MRP2 499 MRP3 246 MRP4 290	UGT 219	MRP1 74 MRP2 146 MRP3 83 MRP4 53

Drug as perpetrator

Target	Modality	Activity
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP3 326	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP4 345	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11956677/	weak
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes [IC50 0.23 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes [IC50 6.8 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes
CYP3A4 2633	inhibitor 4027 Sources: https://openarchive.ki.se/xmlui/handle/10616/43294	yes
MRP1 232	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes
MRP2 625	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/26945713/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:575568	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:575568
ChemicalBook	CB4383893	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4383893
eMolecules	2728596	https://www.emolecules.com/cgi-bin/more?vid=2728596
MolPort	MolPort-003-666-542	https://www.molport.com/shop/molecule-link/MolPort-003-666-542
Selleck Chemicals	atovaquone-atavaquone	http://www.selleckchem.com/products/atovaquone-atavaquone.html
ZINC	ZINC000116473771	http://zinc15.docking.org/substances/ZINC000116473771

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
In vitro and in vivo combination of cepharanthine with anti-malarial drugs.	2014-03-12	24618129
A SYBR Green 1-based in vitro test of susceptibility of Ghanaian Plasmodium falciparum clinical isolates to a panel of anti-malarial drugs.	2013-12-17	24341604
Design, synthesis and biological evaluation of WC-9 analogs as antiparasitic agents.	2013-11	24090919
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013-09-05	23769903
Quinolin-4(1H)-imines are potent antiplasmodial drugs targeting the liver stage of malaria.	2013-06-13	23701465
The antimalarial activities of methylene blue and the 1,4-naphthoquinone 3-[4-(trifluoromethyl)benzyl]-menadione are not due to inhibition of the mitochondrial electron transport chain.	2013-05	23439633
Quinolone-3-diarylethers: a new class of antimalarial drug.	2013-03-20	23515079
4(1H)-Quinolones with liver stage activity against Plasmodium berghei.	2013-01	23129047
Targeting the ERAD pathway via inhibition of signal peptide peptidase for antiparasitic therapeutic design.	2012-12-26	23236186
New naphthoquinones and an alkaloid with in vitro activity against Toxoplasma gondii RH and EGS strains.	2012-12	23000485
Characterization of Plasmodium liver stage inhibition by halofuginone.	2012-05	22438279
Drug screen targeted at Plasmodium liver stages identifies a potent multistage antimalarial drug.	2012-04-15	22396598
Identification and validation of tetracyclic benzothiazepines as Plasmodium falciparum cytochrome bc1 inhibitors.	2011-12-23	22195562
Synthetic chromanol derivatives and their interaction with complex III in mitochondria from bovine, yeast, and Leishmania.	2011-10-17	21809846
Sensitivity of Plasmodium vivax to chloroquine, mefloquine, artemisinin and atovaquone in north-western Thailand.	2011-10	21935647
Novel HIV-1 protease inhibitors (PIs) containing a bicyclic P2 functional moiety, tetrahydropyrano-tetrahydrofuran, that are potent against multi-PI-resistant HIV-1 variants.	2011-04	21282450
In vitro atovaquone/proguanil susceptibility and characterization of the cytochrome b gene of Plasmodium falciparum from different endemic regions of Thailand.	2008-01-28	18226262
Acute hepatitis and atovaquone/proguanil.	2005-11-01	16256055
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Combined effect of atovaquone and pyrrolidine dithiocarbamate in the treatment of acute murine toxoplasmosis.	2004-06	15272229
Efficacy of atovaquone combined with clindamycin against murine infection with a cystogenic (Me49) strain of Toxoplasma gondii.	2002-12	12461021
Plasmodium falciparum: the effects of atovaquone resistance on respiration.	2001-08	11560411
Atovaquone nanosuspensions show excellent therapeutic effect in a new murine model of reactivated toxoplasmosis.	2001-06	11353624
Effects of aerosolized synthetic surfactant, atovaquone, and the combination of these on murine Pneumocystis carinii pneumonia.	1998-04	9534981
Chronic infection with Toxoplasma gondii does not prevent acute disease or colonization of the brain with tissue cysts following reinfection with different strains of the parasite.	1997-06	9194838
Immunodeficient and immunosuppressed mice as models to test anti-Pneumocystis carinii drugs.	1997-02	9021175
Clinically used antimicrobial drugs against experimental pneumocystosis, singly and in combination: analysis of drug interactions and efficacies.	1997-02	9021174
Efficacy of lasalocid against murine Pneumocystis carinii pneumonitis.	1997-01	8980779
Treatment with interleukin 12 in combination with atovaquone or clindamycin significantly increases survival of mice with acute toxoplasmosis.	1997-01	8980778
Evaluation of the activities of rifabutin combined with atovaquone or low-dose of cotrimoxazole for prevention of pneumocystosis and toxoplasmosis in a dual infection rat model.	1996-09-01	8822822
In-vitro activity of macrolides alone and in combination with artemisin, atovaquone, dapsone, minocycline or pyrimethamine against Cryptosporidium parvum.	1996-09	8889715
In vitro and in vivo effects of rifabutin alone or combined with atovaquone against Toxoplasma gondii.	1996-09	8878573
Use of rifabutin in combination with atovaquone, clindamycin, pyrimethamine, or sulfadiazine for treatment of toxoplasmic encephalitis in mice.	1996-05	8793398
Influence of antimicrobial agents on replication and stage conversion of Toxoplasma gondii.	1996	8791704
Nonionic block copolymers potentiate activities of drugs for treatment of infections with Toxoplasma gondii.	1995-12	8593005
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995-11-24	7490723
Acute severe autonomic insufficiency during pentamidine therapy.	1995-10	7481974
Effect of atovaquone and atovaquone drug combinations on prophylaxis of Pneumocystis carinii pneumonia in SCID mice.	1995-04	7785975
Effects of atovaquone and other inhibitors on Pneumocystis carinii dihydroorotate dehydrogenase.	1995-02	7726490
Relative potency of 10 drugs with anti-Pneumocystis carinii activity in an animal model.	1994-10	7930735
In vitro model to assess effect of antimicrobial agents on Encephalitozoon cuniculi.	1994-10	7840584
Rifabutin is active in murine models of toxoplasmosis.	1994-03	8203856
Mutants of Toxoplasma gondii resistant to atovaquone (566C80) or decoquinate.	1993-08	8331476
The activity of atovaquone (566C80) in murine toxoplasmosis is markedly augmented when used in combination with pyrimethamine or sulfadiazine.	1993-02	8421189
In vitro and in vivo activities of the hydroxynaphthoquinone 566C80 against the cyst form of Toxoplasma gondii.	1992-02	1605598
566C80, an antimalarial hydroxynaphthoquinone with broad spectrum: experimental activity against opportunistic parasitic infections of AIDS patients.	1991-11-01	1818143
Evaluation of the effect of drugs on the cyst form of Toxoplasma gondii.	1991-07	1647421
Remarkable in vitro and in vivo activities of the hydroxynaphthoquinone 566C80 against tachyzoites and tissue cysts of Toxoplasma gondii.	1991-02	2024964
Efficacy of a hydroxynaphthoquinone, 566C80, in experimental Pneumocystis carinii pneumonitis.	1990-02	2327770

Patents

Sample Use Guides

In Vivo Use Guide

Dosage for the Prevention of P. jiroveci Pneumonia: 1,500 mg (10 mL) once daily administered with food. Dosage for the Treatment of Mild-to-Moderate P. jiroveci Pneumonia The recommended oral dosage is 750 mg (5 mL) twice daily (total daily dose = 1,500 mg) administered with food for 21 days.

Route of Administration: Oral

In Vitro Use Guide

IC50 of atovaquone against P. jiroveci to be 0.1 to 3.0 mcg/mL.

Name

Type

Language

MALARONE COMPONENT ATOVAQUONE

Preferred Name

English

ATOVAQUONE

Official Name

English

2-(TRANS-4-(P-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-1,4-NAPHTHOQUINONE

Common Name

English

ATOVAQUONE [MART.]

Common Name

English

2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone

Systematic Name

English

MEPRON

Brand Name

English

NSC-759582

Code

English

ATOVAQUONE [USP MONOGRAPH]

Common Name

English

ATOVAQUONE [USAN]

Common Name

English

ATOVAQUONE [USP-RS]

Common Name

English

ATOVAQUONE [VANDF]

Common Name

English

ATOVAQUONE [ORANGE BOOK]

Common Name

English

MALARONE PEDIATRIC COMPONENT ATOVAQUONE

Common Name

English

1,4-NAPHTHALENEDIONE, 2-(4-(4-CHLOROPHENYL)CYCLOHEXYL)-3-HYDROXY-, TRANS-

Common Name

English

atovaquone [INN]

Common Name

English

ATOVAQUONE [JAN]

Common Name

English

ATOVAQUONE [EP MONOGRAPH]

Common Name

English

566C

Code

English

566C80

Code

English

ATOVAQUONE [MI]

Common Name

English

Atovaquone [WHO-DD]

Common Name

English

ATOVAQUONE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277