Buparvaquone

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 ;
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.^{[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]}

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]

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.^{[citation needed]}

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.

[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.

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