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
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-napht ...
s. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of both
ubiquinone
Coenzyme Q, also known as ubiquinone and marketed as CoQ10, is a coenzyme family that is ubiquitous in animals and most bacteria (hence the name ubiquinone). In humans, the most common form is coenzyme Q10 or ubiquinone-10.
It is a 1,4-benzoq ...
and
lawsone
Lawsone (2-hydroxy-1,4-naphthoquinone), also known as hennotannic acid, is a red-orange dye present in the leaves of the henna plant (''Lawsonia inermis''), for which it is named, as well as in the flower of water hyacinth ('' Eichhornia crassipe ...
, with antipneumocystic activity.
Medical uses
Atovaquone is a medication used to treat or prevent:
* For
pneumocystis pneumonia (PCP),
it is used in mild cases, although it is not approved for treatment of severe cases.
* For
toxoplasmosis
Toxoplasmosis is a parasitic disease caused by ''Toxoplasma gondii'', an apicomplexan. Infections with toxoplasmosis are associated with a variety of neuropsychiatric and behavioral conditions. Occasionally, people may have a few weeks or months ...
,
the medication has antiparasitic and therapeutic effects.
* For
malaria
Malaria is a mosquito-borne infectious disease that affects humans and other animals. Malaria causes symptoms that typically include fever, tiredness, vomiting, and headaches. In severe cases, it can cause jaundice, seizures, coma, or death. S ...
, it is one of the two components (along with
proguanil) in the drug
Malarone. Malarone has fewer side effects and is more expensive than
mefloquine. Resistance has been observed.
* For
babesia
''Babesia'', also called ''Nuttallia'', is an apicomplexan parasite that infects red blood cells and is transmitted by ticks. Originally discovered by the Romanian bacteriologist Victor Babeș in 1888, over 100 species of ''Babesia'' have since ...
, it is often used in conjunction with oral
azithromycin
Azithromycin, sold under the brand names Zithromax (in oral form) and Azasite (as an eye drop), is an antibiotic medication used for the treatment of a number of bacterial infections. This includes middle ear infections, strep throat, pneumon ...
.
Trimethoprim/sulfamethoxazole
Trimethoprim/sulfamethoxazole, sold under the brand name Bactrim among others, is a fixed-dose combination antibiotic medication used to treat a variety of bacterial infections. It consists of one part trimethoprim to five parts sulfamethoxazo ...
(TMP-SMX, Bactrim) is generally considered first-line therapy for PCP (not to be confused with sulfadiazine and pyrimethamine, which is first line for toxoplasmosis). However, atovaquone may be used in patients who cannot tolerate, or are allergic to,
sulfonamide
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this group is unreactive. ...
medications such as TMP-SMX. In addition, atovaquone has the advantage of not causing
myelosuppression
Bone marrow suppression also known as myelotoxicity or myelosuppression, is the decrease in production of cells responsible for providing immunity (leukocytes), carrying oxygen (erythrocytes), and/or those responsible for normal blood clotting (t ...
, which is an important issue in patients who have undergone
bone marrow transplantation
Hematopoietic stem-cell transplantation (HSCT) is the transplantation of multipotent hematopoietic stem cells, usually derived from bone marrow, peripheral blood, or umbilical cord blood in order to replicate inside of a patient and to produc ...
.
Atovaquone is given prophylactically to kidney transplant patients to prevent PCP in cases where Bactrim is contraindicated for the patient.
Malaria
Atovaquone, as a
combination
In mathematics, a combination is a selection of items from a set that has distinct members, such that the order of selection does not matter (unlike permutations). For example, given three fruits, say an apple, an orange and a pear, there are th ...
preparation with
proguanil, has been commercially available from
GlaxoSmithKline
GSK plc, formerly GlaxoSmithKline plc, is a British multinational pharmaceutical and biotechnology company with global headquarters in London, England. Established in 2000 by a merger of Glaxo Wellcome and SmithKline Beecham. GSK is the ten ...
since 2000 as Malarone for the treatment and prevention of malaria.
Research
COVID-19
Preliminary research found that atovaquone could inhibit the replication of
SARS-CoV-2
Severe acute respiratory syndrome coronavirus 2 (SARS‑CoV‑2) is a strain of coronavirus that causes COVID-19 (coronavirus disease 2019), the respiratory illness responsible for the ongoing COVID-19 pandemic. The virus previously had a ...
in vitro. Clinical trials of atovaquone for the treatment of
COVID-19
Coronavirus disease 2019 (COVID-19) is a contagious disease caused by a virus, the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The first known case was COVID-19 pandemic in Hubei, identified in Wuhan, China, in December ...
are planned, and ongoing in
USA
The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...
in
December
December is the twelfth and final month of the year in the Julian and Gregorian calendars and is also the last of seven months to have a length of 31 days.
December got its name from the Latin word ''decem'' (meaning ten) because it was or ...
2021.
Atovaquone has also been found to inhibit
human coronavirus OC43
Human coronavirus OC43 (HCoV-OC43) is a member of the species '' Betacoronavirus 1'', which infects humans and cattle. The infecting coronavirus is an enveloped, positive-sense, single-stranded RNA virus that enters its host cell by binding to ...
and
feline coronavirus
Feline coronavirus (FCoV) is a positive-stranded RNA virus that infects cats worldwide. It is a coronavirus of the species '' Alphacoronavirus 1'' which includes canine coronavirus (CCoV) and porcine transmissible gastroenteritis coronavirus (T ...
in vitro.
Veterinary use
Atovaquone is used in livestock veterinary cases of
babesiosis
Babesiosis or piroplasmosis is a malaria-like parasitic disease caused by infection with a eukaryotic parasite in the order Piroplasmida, typically a ''Babesia'' or ''Theileria'', in the phylum Apicomplexa. Human babesiosis transmission via ti ...
in
cattle
Cattle (''Bos taurus'') are large, domesticated, cloven-hooved, herbivores. They are a prominent modern member of the subfamily Bovinae and the most widespread species of the genus ''Bos''. Adult females are referred to as cows and adult mal ...
, especially if
imidocarb
Imidocarb is a urea derivative used in veterinary medicine as an antiprotozoal agent for the treatment of infection with ''Babesia'' (babesiosis
Babesiosis or piroplasmosis is a malaria-like parasitic disease caused by infection with a eukary ...
resistance is a concern.
References
Further reading
*
External links
*
{{Authority control
Antimalarial agents
Antiprotozoal agents
1,4-Naphthoquinones
Chloroarenes
GSK plc brands
Hydroxynaphthoquinones