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=C(C=CC=C4)C1=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 8297
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 8297

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 8429	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 7.2264961E11

C_max

Value	Dose	Analyte	Population
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 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
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
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
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
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

F_unbound

Value	Dose	Analyte	Population
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 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	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 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 Page: p.559	unhealthy n = 6 Health Status: unhealthy Condition: HIV inection Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/8851570 Page: p.559	Sources: https://pubmed.ncbi.nlm.nih.gov/8851570 Page: p.559
31500 mg single, oral Overdose Dose: 31500 mg Route: oral Route: single Dose: 31500 mg Co-administed with:: dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.16	unhealthy Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.16	Other AEs: Methemoglobinemia, Rash... Other AEs: Methemoglobinemia Rash Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.16
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 Page: p.12	unhealthy n = 175 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 175 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.12	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 Page: p.12
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 Page: p.12	unhealthy n = 203 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 203 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.12	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.12
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 Page: p.13	unhealthy n = 203 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 203 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.13	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 Page: p.13
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 Page: p.15	unhealthy n = 73 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 73 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.15	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 Page: p.15

AEs

AE	Significance	Dose	Population
Methemoglobinemia		31500 mg single, oral Overdose Dose: 31500 mg Route: oral Route: single Dose: 31500 mg Co-administed with:: dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.16	unhealthy Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.16
Rash		31500 mg single, oral Overdose Dose: 31500 mg Route: oral Route: single Dose: 31500 mg Co-administed with:: dapsone Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.16	unhealthy Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.16
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 Page: p.12	unhealthy n = 175 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 175 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.12
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 Page: p.12	unhealthy n = 175 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 175 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.12
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 Page: p.12	unhealthy n = 175 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 175 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.12
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 Page: p.12	unhealthy n = 203 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 203 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.12
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 Page: p.13	unhealthy n = 203 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 203 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.13
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 Page: p.13	unhealthy n = 203 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 203 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.13
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 Page: p.13	unhealthy n = 203 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 203 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.13
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 Page: p.15	unhealthy n = 73 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 73 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.15
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 Page: p.15	unhealthy n = 73 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 73 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.15
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 Page: p.15	unhealthy n = 73 Health Status: unhealthy Condition: Pneumocystis carinii pneumonia Population Size: 73 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/020500s010lbl.pdf Page: p.15

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 BCRP 699 BSEP 402 MRP1 106 MRP2 383 MRP3 157 MRP4 204	UGT 192	MRP1 48 MRP2 111 MRP3 53 MRP4 32

Drug as perpetrator

Target	Modality	Activity
MRP1 172	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP3 207	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP4 238	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11956677/	weak
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes [IC50 0.23 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes [IC50 6.8 uM]
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes
CYP3A4 1925	inhibitor 3277 Sources: https://openarchive.ki.se/xmlui/handle/10616/43294	yes
MRP1 172	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes
MRP2 475	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/25218605/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 192	substrate 3367 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
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
eMolecules	2728596	https://www.emolecules.com/cgi-bin/more?vid=2728596

PubMed

Title	Date	PubMed
Efficacy of a hydroxynaphthoquinone, 566C80, in experimental Pneumocystis carinii pneumonitis.	1990 Feb	2327770
566C80, an antimalarial hydroxynaphthoquinone with broad spectrum: experimental activity against opportunistic parasitic infections of AIDS patients.	1991 Nov-Dec	1818143
The activity of atovaquone (566C80) in murine toxoplasmosis is markedly augmented when used in combination with pyrimethamine or sulfadiazine.	1993 Feb	8421189
Relative potency of 10 drugs with anti-Pneumocystis carinii activity in an animal model.	1994 Oct	7930735
In vitro model to assess effect of antimicrobial agents on Encephalitozoon cuniculi.	1994 Oct	7840584
Nonionic block copolymers potentiate activities of drugs for treatment of infections with Toxoplasma gondii.	1995 Dec	8593005
Influence of antimicrobial agents on replication and stage conversion of Toxoplasma gondii.	1996	8791704
Use of rifabutin in combination with atovaquone, clindamycin, pyrimethamine, or sulfadiazine for treatment of toxoplasmic encephalitis in mice.	1996 May	8793398
Efficacy of lasalocid against murine Pneumocystis carinii pneumonitis.	1997 Jan	8980779
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 Jun	9194838
Effects of aerosolized synthetic surfactant, atovaquone, and the combination of these on murine Pneumocystis carinii pneumonia.	1998 Apr	9534981
Resistance mutations reveal the atovaquone-binding domain of cytochrome b in malaria parasites.	1999 Aug	10447880
Atovaquone-proguanil versus chloroquine-proguanil for malaria prophylaxis in non-immune travellers: a randomised, double-blind study. Malarone International Study Team.	2000 Dec 2	11130385
Plasmodium falciparum: the effects of atovaquone resistance on respiration.	2001 Aug	11560411
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.	2001 Jan	11124226
Atovaquone nanosuspensions show excellent therapeutic effect in a new murine model of reactivated toxoplasmosis.	2001 Jun	11353624
Efficacy of atovaquone combined with clindamycin against murine infection with a cystogenic (Me49) strain of Toxoplasma gondii.	2002 Dec	12461021
Combined effect of atovaquone and pyrrolidine dithiocarbamate in the treatment of acute murine toxoplasmosis.	2004 Jun	15272229
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
In vitro atovaquone/proguanil susceptibility and characterization of the cytochrome b gene of Plasmodium falciparum from different endemic regions of Thailand.	2008 Jan 28	18226262
New naphthoquinones and an alkaloid with in vitro activity against Toxoplasma gondii RH and EGS strains.	2012 Dec	23000485
Targeting the ERAD pathway via inhibition of signal peptide peptidase for antiparasitic therapeutic design.	2012 Dec 26	23236186
A SYBR Green 1-based in vitro test of susceptibility of Ghanaian Plasmodium falciparum clinical isolates to a panel of anti-malarial drugs.	2013 Dec 17	24341604
Quinolin-4(1H)-imines are potent antiplasmodial drugs targeting the liver stage of malaria.	2013 Jun 13	23701465
Quinolone-3-diarylethers: a new class of antimalarial drug.	2013 Mar 20	23515079
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 May	23439633
Design, synthesis and biological evaluation of WC-9 analogs as antiparasitic agents.	2013 Nov	24090919
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903
In vitro and in vivo combination of cepharanthine with anti-malarial drugs.	2014 Mar 12	24618129
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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

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

MALARONE COMPONENT ATOVAQUONE

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 COMPONENT OF MALARONE PEDIATRIC

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 COMPONENT OF MALARONE

Common Name

English

ATOVAQUONE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277