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
Biological 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 N
PubChem (CID)	74989
DrugBank	DB01117 Y
ChemSpider	10482034 Y
UNII	Y883P1Z2LT Y
KEGG	D00236 Y
ChEBI	CHEBI:575568 Y
ChEMBL	CHEMBL1450 Y
ECHA InfoCard	100.158.738
Chemical and physical data
Formula	C22H19ClO3
Molar mass	366.837 g/mol
3D model (Jmol)	Interactive image
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- Y Key:KUCQYCKVKVOKAY-CTYIDZIISA-N Y
NY (what is this?)

Atovaquone (alternative spelling: atavaquone) is a chemical compound that belongs to the class of naphthoquinones. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of ubiquinone, with antipneumocystic activity. It is manufactured in the US in the liquid form, or oral suspension, under the brand name Mepron.

Atovaquone is a medication used to treat or prevent:

Trimethoprim/sulfamethoxazole (TMP-SMX, Bactrim) is generally considered first-line therapy for PCP or toxoplasmosis. However, atovaquone may be used in patients who cannot tolerate, or are allergic to, sulfonamide medications such as TMP-SMX. In addition, atovaquone has the advantage of not causing myelosuppression, which is an important issue in patients who have undergone bone marrow transplantation.

Atovaquone, as a combination preparation with proguanil, has been commercially available from GlaxoSmithKline since 2000 as Malarone for the treatment and prevention of malaria.