Buparvaquone

Buparvaquone
Clinical data
ATCvet code	QP51AX22 (WHO) ;
Identifiers
	IUPAC name 2-((4-tert-butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone;
CAS Number	88426-33-9 ;
ChemSpider	10807457 ;
UNII	0354RT7LG4;
ChEMBL	ChEMBL292009 ;
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 ; Key:KLLIVCPQDTYMLC-UHFFFAOYSA-N ;
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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. It is the only really effective commercial therapeutic product against bovine theileriosis, where it has been used since the late 1980s.

Industrial production

It was first produced in Great Britain, then in Germany. Its patent expired in the mid-2000s, and was then produced in different countries, e.g., India and Iran.

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]

Molecular target

Buparvaquone resistance appears to be associated with parasite mutations in the Q_o quinone-binding site of mitochondrial cytochrome b.[2] 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.

References

Abdou TA, Abou-El-naga TR, Mahmoud MA (2005). "Clinicopathological Studies on Theileria Annulata Infection in Siwa Oasis in Egypt" (PDF). BS. Vet. Med. J. 15 (2): 40–6.
Sharifiyazdi H, Namazi F, Oryan A, Shahriari R, Razavi M (July 2012). "Point mutations in the Theileria annulata cytochrome b gene is associated with buparvaquone treatment failure". Veterinary Parasitology. 187 (3–4): 431–5. doi:10.1016/j.vetpar.2012.01.016. PMID 22305656.

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[1] Abdou TA, Abou-El-naga TR, Mahmoud MA (2005). "Clinicopathological Studies on Theileria Annulata Infection in Siwa Oasis in Egypt" (PDF). BS. Vet. Med. J. 15 (2): 40–6.

[2] Sharifiyazdi H, Namazi F, Oryan A, Shahriari R, Razavi M (July 2012). "Point mutations in the Theileria annulata cytochrome b gene is associated with buparvaquone treatment failure". Veterinary Parasitology. 187 (3–4): 431–5. doi:10.1016/j.vetpar.2012.01.016. PMID 22305656.