Atovaquone

Atovaquone
Clinical data
Trade names	Mepron
AHFS/Drugs.com	Monograph
MedlinePlus	a693003
Routes of; administration	By mouth
ATC code	P01AX06 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Elimination half-life	2.2–3.2 days
Identifiers
	IUPAC name trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione;
CAS Number	95233-18-4 ;
PubChem CID	74989;
DrugBank	DB01117 ;
ChemSpider	10482034 ;
UNII	Y883P1Z2LT;
KEGG	D00236 ;
ChEBI	CHEBI:575568 ;
ChEMBL	ChEMBL1450 ;
CompTox Dashboard (EPA)	DTXSID7022629 ;
ECHA InfoCard	100.158.738
Chemical and physical data
Formula	C22H19ClO3
Molar mass	366.84 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	216 to 219 °C (421 to 426 °F)
	SMILES OC=2C(=O)c1ccccc1C(=O)C=2[C@@H]3CC[C@H](CC3)c4ccc(Cl)cc4;
	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- ; Key:KUCQYCKVKVOKAY-CTYIDZIISA-N ;
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Atovaquone, sold under the brand name Mepron, is an naphthoquinone antiprotozoal medication used in the prevention and treatment Pneumocystis jirovecii pneumonia (PCP), and malaria (in combination with proguanil), as well as for treatment of babesiosis (in combination with azithromycin).

Atovaquone is an analogue of ubiquinone (coenzyme Q10) and exerts its pharmaceutical effects by binding to the ubiquinone binding site on the parasitic mitochondrial cytochrome bc1 complex, thus inhibiting a step of protozoal pyrimidine synthesis.

Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of both ubiquinone and lawsone.