Atovaquone

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Atovaquone
Atovaquone Structural Formula V.1.svg
Atovaquone-from-xtal-Mercury-3D-bs.png
Clinical data
Trade names Mepron
AHFS/Drugs.com Monograph
MedlinePlus a693003
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 2.2–3.2 days
Identifiers
  • trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.158.738 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H19ClO3
Molar mass 366.84 g·mol−1
3D model (JSmol)
Melting point 216 to 219 °C (421 to 426 °F)
  • OC=2C(=O)c1ccccc1C(=O)C=2[C@@H]3CC[C@H](CC3)c4ccc(Cl)cc4
  • InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15- Yes check.svgY
  • Key:KUCQYCKVKVOKAY-CTYIDZIISA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Atovaquone, sold under the brand name Mepron, is an antimicrobial medication for the prevention and treatment of Pneumocystis jirovecii pneumonia (PCP). [2]

Contents

Atovaquone is a chemical compound that belongs to the class of naphthoquinones. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of both ubiquinone and lawsone.

Medical uses

Atovaquone is a medication used to treat or prevent:

Trimethoprim/sulfamethoxazole (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 medications such as TMP-SMX. In addition, atovaquone has the advantage of not causing myelosuppression, which is an important issue in patients who have undergone bone marrow transplantation.[ citation needed ]

Atovaquone is given prophylactically to kidney transplant patients to prevent PCP in cases where Bactrim is contraindicated for the patient.[ medical citation needed ]

Malaria

Atovaquone, as a combination preparation with proguanil, has been commercially available from GlaxoSmithKline 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 in vitro. [9] Clinical trials of atovaquone for the treatment of COVID-19 are planned, [10] [11] and ongoing in United States in December 2021. [12] [ needs update ]

Atovaquone has also been found to inhibit human coronavirus OC43 and feline coronavirus in vitro. [13]

In newer researches, atovaquone did not demonstrate evidence of enhanced SARS-CoV-2 viral clearance compared with placebo. [14]

Veterinary use

Atovaquone is used in livestock veterinary cases of babesiosis in cattle, especially if imidocarb resistance is a concern. [15]

Related Research Articles

<span class="mw-page-title-main">Trimethoprim</span> Antibiotic

Trimethoprim (TMP) is an antibiotic used mainly in the treatment of bladder infections. Other uses include for middle ear infections and travelers' diarrhea. With sulfamethoxazole or dapsone it may be used for Pneumocystis pneumonia in people with HIV/AIDS. It is taken orally.

<span class="mw-page-title-main">Pentamidine</span> Medical antimicrobial drug

Pentamidine is an antimicrobial medication used to treat African trypanosomiasis, leishmaniasis, Balamuthia infections, babesiosis, and to prevent and treat pneumocystis pneumonia (PCP) in people with poor immune function. In African trypanosomiasis it is used for early disease before central nervous system involvement, as a second line option to suramin. It is an option for both visceral leishmaniasis and cutaneous leishmaniasis. Pentamidine can be given by injection into a vein or muscle or by inhalation.

<span class="mw-page-title-main">Mefloquine</span> Pharmaceutical drug

Mefloquine, sold under the brand name Lariam among others, is a medication used to prevent or treat malaria. When used for prevention it is typically started before potential exposure and continued for several weeks after potential exposure. It can be used to treat mild or moderate malaria but is not recommended for severe malaria. It is taken by mouth.

<span class="mw-page-title-main">Azithromycin</span> Antibiotic

Azithromycin, sold under the brand names Zithromax and Azasite, is an antibiotic medication used for the treatment of a number of bacterial infections. This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, and certain other intestinal infections. Along with other medications, it may also be used for malaria. It is administered by mouth, into a vein, or into the eye.

<span class="mw-page-title-main">Trimethoprim/sulfamethoxazole</span> Combination of two antibiotic drugs

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 sulfamethoxazole. It is used to treat urinary tract infections, methicillin-resistant Staphylococcus aureus (MRSA) skin infections, travelers' diarrhea, respiratory tract infections, and cholera, among others. It is used both to treat and prevent pneumocystis pneumonia and toxoplasmosis in people with HIV/AIDS and other causes of immunosuppression. It can be given orally or intravenous infusion.

<span class="mw-page-title-main">Folinic acid</span> Derivative of folic acid used in cancer treatment

Folinic acid, also known as leucovorin, is a medication used to decrease the toxic effects of methotrexate and pyrimethamine. It is also used in combination with 5-fluorouracil to treat colorectal cancer and pancreatic cancer, may be used to treat folate deficiency that results in anemia, and methanol poisoning. It is taken by mouth, injection into a muscle, or injection into a vein.

<span class="mw-page-title-main">Sulfamethoxazole</span> Chemical compound

Sulfamethoxazole is an antibiotic. It is used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Escherichia coli and Listeria monocytogenes.

<span class="mw-page-title-main">Primaquine</span> Pharmaceutical drug

Primaquine is a medication used to treat and prevent malaria and to treat Pneumocystis pneumonia. Specifically it is used for malaria due to Plasmodium vivax and Plasmodium ovale along with other medications and for prevention if other options cannot be used. It is an alternative treatment for Pneumocystis pneumonia together with clindamycin. It is taken by mouth.

<span class="mw-page-title-main">Opportunistic infection</span> Infection caused by pathogens that take advantage of an opportunity not normally available

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<span class="mw-page-title-main">Proguanil</span> Chemical compound

Proguanil, also known as chlorguanide and chloroguanide, is a medication used to treat and prevent malaria. It is often used together with chloroquine or atovaquone. When used with chloroquine the combination will treat mild chloroquine resistant malaria. It is taken by mouth.

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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 been identified.

<i>Pneumocystis jirovecii</i> Species of fungus

Pneumocystis jirovecii is a yeast-like fungus of the genus Pneumocystis. The causative organism of Pneumocystis pneumonia, it is an important human pathogen, particularly among immunocompromised hosts. Prior to its discovery as a human-specific pathogen, P. jirovecii was known as P. carinii.

<i>Pneumocystis</i> pneumonia Medical condition

Pneumocystis pneumonia (PCP), also known as Pneumocystis jirovecii pneumonia (PJP), is a form of pneumonia that is caused by the yeast-like fungus Pneumocystis jirovecii.

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Atovaquone/proguanil, sold under the brand name Malarone among others, is a fixed-dose combination medication used to treat and prevent malaria, including chloroquine-resistant malaria. It contains atovaquone and proguanil. It is not recommended for severe or complicated malaria. It is taken by mouth.

Pafuramidine is an experimental drug for the treatment of pneumocystis pneumonia (PCP). In 2006, pafuramidine was given orphan drug status by the US Food and Drug Administration for PCP in patients with HIV/AIDS. Preliminary clinical trials indicated that pafuramide was effective against pneumocystis pneumonia and had the potential for fewer side effects than the standard treatment with trimethoprim/sulfamethoxazole (TMP-SMX).

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<span class="mw-page-title-main">Sandy Ford</span> American drug technician, identifier of first known AIDS cluster

Sandy Ford was a drug technician for the Centers for Disease Control in Atlanta, Georgia. In April 1981, she identified unusual clusters of young homosexual patients in New York and California with pneumocystis pneumonia and Kaposi's sarcoma and alerted her supervisor about it. Those patients had HIV/AIDS; pneumocystis pneumonia and Kaposi's sarcoma were later found to be AIDS-defining diseases.

References

  1. ↑ "Wellvone 750mg/5ml oral suspension - Summary of Product Characteristics (SmPC)". (emc). 28 November 2019. Retrieved 18 September 2020.
  2. ↑ "Atovaquone Oral SUSPENSION- atovaquone suspension". DailyMed. 10 December 2019. Retrieved 18 September 2020.
  3. ↑ Hughes W, Leoung G, Kramer F, Bozzette SA, Safrin S, Frame P, et al. (May 1993). "Comparison of atovaquone (566C80) with trimethoprim-sulfamethoxazole to treat Pneumocystis carinii pneumonia in patients with AIDS". The New England Journal of Medicine. 328 (21): 1521–1527. doi: 10.1056/NEJM199305273282103 . PMID   8479489.
  4. ↑ Dohn MN, Weinberg WG, Torres RA, Follansbee SE, Caldwell PT, Scott JD, et al. (August 1994). "Oral atovaquone compared with intravenous pentamidine for Pneumocystis carinii pneumonia in patients with AIDS. Atovaquone Study Group". Annals of Internal Medicine. 121 (3): 174–180. doi:10.7326/0003-4819-121-3-199408010-00003. PMID   7880228. S2CID   24263604.
  5. ↑ Djurković-Djaković O, Milenković V, Nikolić A, Bobić B, Grujić J (December 2002). "Efficacy of atovaquone combined with clindamycin against murine infection with a cystogenic (Me49) strain of Toxoplasma gondii". The Journal of Antimicrobial Chemotherapy. 50 (6): 981–987. doi: 10.1093/jac/dkf251 . PMID   12461021.
  6. ↑ Malarone: New Malaria Medication With Fewer Side-effects Archived May 14, 2006, at the Wayback Machine
  7. ↑ Färnert A, Lindberg J, Gil P, Swedberg G, Berqvist Y, Thapar MM, et al. (March 2003). "Evidence of Plasmodium falciparum malaria resistant to atovaquone and proguanil hydrochloride: case reports". BMJ. 326 (7390): 628–629. doi:10.1136/bmj.326.7390.628. PMC   151974 . PMID   12649236.
  8. ↑ Krause PJ, Lepore T, Sikand VK, Gadbaw J, Burke G, Telford SR, et al. (November 2000). "Atovaquone and azithromycin for the treatment of babesiosis". The New England Journal of Medicine. 343 (20): 1454–1458. doi: 10.1056/NEJM200011163432004 . PMID   11078770.
  9. ↑ Farag A, Wang P, et al. (May 2020). "Identification of Atovaquone, Ouabain and Mebendazole as FDA-Approved Drugs Targeting SARS-CoV-2". chemRxiv (preprint). doi:10.26434/chemrxiv.12003930.v4. S2CID   219428383 . Retrieved 20 June 2020.
  10. ↑ "Atovaquone and Azithromycin Combination for Confirmed COVID-19 Infection". ClinicalTrials.gov. Retrieved 22 October 2020.
  11. ↑ "Atovaquone for Treatment of COVID-19". ClinicalTrials.gov. Retrieved 22 October 2020.
  12. ↑ KATHRINE EMILIE KRISTENSEN (10 December 2021). "Ny forskning finder lægemiddel mod corona: 'Kan redde menneskeliv'". B.T. (in Danish). Retrieved 10 December 2021.
  13. ↑ Yang CW, Peng TT, Hsu HY, Lee YZ, Wu SH, Lin WH, et al. (August 2020). "Repurposing old drugs as antiviral agents for coronaviruses". Biomedical Journal. 43 (4): 368–374. doi: 10.1016/j.bj.2020.05.003 . PMC   7245249 . PMID   32563698.
  14. ↑ Jain MK, De Lemos JA, McGuire DK, Ayers C, Eitson JL, Sanchez CL, et al. (2022). "Atovaquone for treatment of COVID-19: A prospective randomized, double-blind, placebo-controlled clinical trial". Frontiers in Pharmacology. 13: 1020123. doi: 10.3389/fphar.2022.1020123 . PMC   9561237 . PMID   36249792.
  15. ↑ Vial HJ, Gorenflot A (May 2006). "Chemotherapy against babesiosis". Veterinary Parasitology. 138 (1–2): 147–160. doi:10.1016/j.vetpar.2006.01.048. PMID   16504402.

Further reading

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