Buparvaquone is a

naphthoquinone Naphthoquinones constitute a class of organic compounds structurally related to naphthalene. Two isomers are common for the parent naphthoquinones: * 1,2-Naphthoquinone * 1,4-Naphthoquinone Natural products * Alkannin * Hexahydroxy-1,4-nap ...

antiprotozoal Antiprotozoal agents ( ATC code: ATC P01) is a class of pharmaceuticals used in treatment of protozoan infection. A paraphyletic group, protozoans have little in common with each other. For example, '' Entamoeba histolytica'', a unikont eukary ...

drug related to

atovaquone Atovaquone, sold under the brand name Mepron, is an antimicrobial medication for the prevention and treatment of ''Pneumocystis jirovecii'' pneumonia (PCP). Atovaquone is a chemical compound that belongs to the class of naphthoquinones. Atova ...

. It is a promising compound for the therapy and prophylaxis of all forms of theileriosis. Buparvaquone has been shown to have anti-

leishmania ''Leishmania'' () is a genus of parasitic protozoans, single-celled eukaryotic organisms of the trypanosomatid group that are responsible for the disease leishmaniasis. The parasites are transmitted by sandflies of the genus '' Phlebotomus'' ...

l 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 ''Peganum harmala'', commonly called wild rue, Syrian rue, African rue, esfand or espand,Mahmoud OmidsalaEsfand: a common weed found in Persia, Central Asia, and the adjacent areasEncyclopædia Iranica Vol. VIII, Fasc. 6, pp. 583–584. Origina ...

''. 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 Great Britain is an island in the North Atlantic Ocean off the north-west coast of continental Europe, consisting of the countries England, Scotland, and Wales. With an area of , it is the largest of the British Isles, the List of European ...

, then in

Germany Germany, officially the Federal Republic of Germany, is a country in Central Europe. It lies between the Baltic Sea and the North Sea to the north and the Alps to the south. Its sixteen States of Germany, constituent states have a total popu ...

. Its patent expired in the mid-2000s, and was then produced in different countries such as

India India, officially the Republic of India, is a country in South Asia. It is the List of countries and dependencies by area, seventh-largest country by area; the List of countries by population (United Nations), most populous country since ...

and

Iran Iran, officially the Islamic Republic of Iran (IRI) and also known as Persia, is a country in West Asia. It borders Iraq to the west, Turkey, Azerbaijan, and Armenia to the northwest, the Caspian Sea to the north, Turkmenistan to the nort ...

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.

Viruses

Buparvaquone has been shown to inhibit completely

vaccinia The vaccinia virus (VACV or VV) is a large, complex, enveloped virus belonging to the poxvirus family. It has a linear, double-stranded DNA genome approximately 190 kbp in length, which encodes approximately 250 genes. The dimensions of the ...

virus in cell based assay in human cell line.

Molecular target

Buparvaquone resistance appears to be associated with parasite mutations in the Q_o quinone-binding site of mitochondrial

cytochrome b Cytochrome b is a protein found in the membranes of aerobic cells. In eukaryotic mitochondria (inner membrane) and in aerobic prokaryotes, cytochrome b is a component of respiratory chain complex III () — also known as the bc1 complex or ubiq ...

. 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 The coenzyme Q : cytochrome ''c'' – oxidoreductase, sometimes called the cytochrome ''bc''1 complex, and at other times complex III, is the third complex in the electron transport chain (), playing a critical role in biochemical generation of ...

References

{{reflist Antiprotozoal agents 1,4-Naphthoquinones