Buparvaquone

Buparvaquone is a naphthoquinone antiprotozoal drug related to atovaquone. It is a promising compound for the therapy and prophylaxis of all forms of theileriosis. Buparvaquone has been shown to have anti-leishmanial activity in vitro. It can be used to treat bovine East Coast fever protozoa in vitro, along with the only other substance known – Peganum harmala.^{[citation needed]} It is the only really effective commercial therapeutic product against bovine theileriosis, where it has been used since the late 1980s.^{[citation needed]}

Buparvaquone

Clinical data
ATCvet code	QP51EX03 (WHO)
Identifiers
IUPAC name 2-((4-tert-Butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone
CAS Number	88426-33-9 N
ChemSpider	10807457 Y
UNII	0354RT7LG4
ChEMBL	ChEMBL292009 N
CompTox Dashboard (EPA)	DTXSID4057849
ECHA InfoCard	100.115.556
Chemical and physical data
Formula	C21H26O3
Molar mass	326.436 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)C3CCC(C\C2=C(/O)C(=O)c1ccccc1C2=O)CC3
InChI InChI=1S/C21H26O3/c1-21(2,3)14-10-8-13(9-11-14)12-17-18(22)15-6-4-5-7-16(15)19(23)20(17)24/h4-7,13-14,24H,8-12H2,1-3H3 Y Key:KLLIVCPQDTYMLC-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Industrial production

It was first produced in Great Britain, then in Germany.^{[citation needed]} Its patent expired in the mid-2000s, and was then produced in different countries such as India and Iran.^{[citation needed]}

Use in bovine theileriosis

Using a single dose of 2.5 mg/kg, the recovery rate of curable cases is 90 to 98%. In tropical theileriosis, a dosage of 2.0 mg/kg has the same efficacy. Body temperature returns to normal in two to five days. Parasitemia lowers from 12% on day 0 to 5% the next day, then to 1% by day 5 and none at day 7.^[1]

Viruses

Buparvaquone has been shown to inhibit completely vaccinia virus in cell based assay in human cell line.^[2]

Molecular target

Buparvaquone resistance appears to be associated with parasite mutations in the Q_o quinone-binding site of mitochondrial cytochrome b.^[3] Its mode of action is thus likely to be similar to that of the antimalarial drug atovaquone, a similar 2-hydroxy-1,4-naphthoquinone that binds to the Q_o site of cytochrome b thus inhibiting Coenzyme Q – cytochrome c reductase.^{[citation needed]}