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This repository is under review for potential modification in compliance with Administration directives.

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 of ATOVAQUONE

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

Molecular Formula C22H19ClO3
Molecular Weight 366.837
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q08210
Gene ID: 3885966.0
Gene Symbol: NA
Target Organism: Plasmodium falciparum (isolate 3D7)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15.1 μg/mL
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
324 μg × h/mL
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
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
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
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%
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%
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%
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%
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%
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%
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%
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

Doses

DosePopulationAdverse 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:
unhealthy
Health Status: unhealthy
Sources:
31500 mg single, oral
Overdose
Dose: 31500 mg
Route: oral
Route: single
Dose: 31500 mg
Sources:
unhealthy
Other AEs: Methemoglobinemia, Rash...
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:
unhealthy
Disc. AE: Rash, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Rash (grade 1-2, 6%)
Diarrhea (4%)
Nausea (3%)
Sources:
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:
unhealthy
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (4%)
Sources:
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:
unhealthy
Disc. AE: Vomiting, ALT increased...
AEs leading to
discontinuation/dose reduction:
Vomiting (<1%)
ALT increased (2%)
Aspartate aminotransferase increase (2%)
Sources:
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:
unhealthy
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:
AEs

AEs

AESignificanceDosePopulation
Methemoglobinemia
31500 mg single, oral
Overdose
Dose: 31500 mg
Route: oral
Route: single
Dose: 31500 mg
Sources:
unhealthy
Rash
31500 mg single, oral
Overdose
Dose: 31500 mg
Route: oral
Route: single
Dose: 31500 mg
Sources:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
PubMed

PubMed

TitleDatePubMed
Efficacy of a hydroxynaphthoquinone, 566C80, in experimental Pneumocystis carinii pneumonitis.
1990 Feb
566C80, an antimalarial hydroxynaphthoquinone with broad spectrum: experimental activity against opportunistic parasitic infections of AIDS patients.
1991 Nov-Dec
Relative potency of 10 drugs with anti-Pneumocystis carinii activity in an animal model.
1994 Oct
Influence of antimicrobial agents on replication and stage conversion of Toxoplasma gondii.
1996
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
Resistance mutations reveal the atovaquone-binding domain of cytochrome b in malaria parasites.
1999 Aug
Synergistic effect of clindamycin and atovaquone in acute murine toxoplasmosis.
1999 Sep
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Sensitivity of Plasmodium vivax to chloroquine, mefloquine, artemisinin and atovaquone in north-western Thailand.
2011 Oct
Design, synthesis and biological evaluation of WC-9 analogs as antiparasitic agents.
2013 Nov
In vitro and in vivo combination of cepharanthine with anti-malarial drugs.
2014 Mar 12
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

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
IC50 of atovaquone against P. jiroveci to be 0.1 to 3.0 mcg/mL.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:10:59 GMT 2025
Edited
by admin
on Mon Mar 31 18:10:59 GMT 2025
Record UNII
Y883P1Z2LT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MALARONE COMPONENT ATOVAQUONE
Preferred Name English
ATOVAQUONE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
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
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
FDA ORPHAN DRUG 48890
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
FDA ORPHAN DRUG 66692
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
FDA ORPHAN DRUG 48990
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
NDF-RT N0000175482
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
WHO-ATC P01AX06
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
FDA ORPHAN DRUG 66792
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
LIVERTOX NBK548592
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
NDF-RT N0000175485
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
Code System Code Type Description
WIKIPEDIA
ATOVAQUONE
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
RXCUI
60212
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY RxNorm
HSDB
7083
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
NCI_THESAURUS
C28838
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
MERCK INDEX
m2127
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB01117
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
ChEMBL
CHEMBL1450
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
INN
6914
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
LACTMED
Atovaquone
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
FDA UNII
Y883P1Z2LT
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
MESH
D053626
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
RS_ITEM_NUM
1044651
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
DAILYMED
Y883P1Z2LT
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
SMS_ID
100000086636
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
LACTMED
Atovaquone and Proquanil
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
CAS
95233-18-4
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
CHEBI
575568
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
USAN
EE-53
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
NSC
759582
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
DRUG CENTRAL
258
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
EVMPD
SUB05602MIG
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID7022629
Created by admin on Mon Mar 31 18:10:59 GMT 2025 , Edited by admin on Mon Mar 31 18:10:59 GMT 2025
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
calculated on the anhydrous and organic solvent-free basis
ASSAY (HPLC)
USP
BINDER->LIGAND
BINDING
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC