Atovaquone

Title: Atovaquone
CAS Registry Number: 95233-18-4
CAS Name: 2-[trans-4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
Additional Names: trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
Manufacturers' Codes: 566C80; BW-566C; BW-566C-80
Trademarks: Mepron (GSK); Wellvone (GSK)
Molecular Formula: C22H19ClO3
Molecular Weight: 366.84
Percent Composition: C 72.03%, H 5.22%, Cl 9.66%, O 13.08%
Literature References: Hydroxynaphthoquinone derivative that inhibits mitochondrial electron transport. Prepn: A. T. Hudson, A. W. Randall, EP 123238; eidem, US 5053432 (1984, 1991 both to Burroughs Wellcome). Antiprotozoal activity, metabolism, and pharmacokinetics: A. T. Hudson et al., Drugs Exp. Clin. Res. 17, 427 (1991). Mechanism of action study: M. Fry, M. Pudney, Biochem. Pharmacol. 43, 1545 (1992). Clinical trial for prevention of pneumocystis pneumonia in AIDS patients: W. M. El-Sadr et al., N. Engl. J. Med. 339, 1889 (1998).
Properties: Crystals from acetonitrile, mp 216-219°. Practically insol in water.
Melting point: mp 216-219°
Therap-Cat: Antipneumocystic.
Keywords: Antipneumocystic.
Atractyloside Atracurium Besylate Atranorin Atrasentan Atrazine

Atovaquone
Atovaquone Structural Formula V.1.svg
Atovaquone sf.png
Systematic (IUPAC) name
trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
Clinical data
Trade names Mepron
AHFS/Drugs.com monograph
MedlinePlus a693003
Legal status PoM (UK), Rx [US]
Routes oral only
Pharmacokinetic data
Half-life 2.2 to 3.2 days
Identifiers
CAS number 94015-53-9 N
ATC code P01AX06
PubChem CID 74989
DrugBank DB01117
ChemSpider 10482034 YesY
UNII Y883P1Z2LT YesY
KEGG D00236 YesY
ChEBI CHEBI:575568 YesY
ChEMBL CHEMBL1450 YesY
Chemical data
Formula C22H19ClO3 
Mol. mass 366.837 g/mol
 N (what is this?)  (verify)

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.[1]