Atovaquone

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An antibiotic with activity against certain types of protozoa. Atovaquone is used for the treatment of mild to moderate pneumonia caused by Pneumocystis jirovecii (which is most common in people with AIDS); it is prescribed for people who cannot tolerate co-trimoxazole, and it should be taken with food. It is available as a suspension on prescription only. Atovaquone is also used in combination with proguanil hydrochloride for the treatment of falciparum malaria.

Side effects:
include diarrhoea, nausea, and vomiting (which may hinder its absorption), headache, insomnia, rash, and fever.

Precautions:
atovaquone should be used with caution by elderly people, pregnant women, and people with liver or kidney disease. It should not be taken by women who are breastfeeding.

Interactions with other drugs:

Antibiotics rifabutin, rifampicin, and tetracycline reduce the plasma concentration of atovaquone to the extent that it may not be effective.
Metoclopramide reduces the plasma concentration (and possibly the effectiveness) of atovaquone.

Proprietary preparations:
Wellvone; Malarone (combined with proguanil).

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A hydroxynaphthoquinone effective against protozoa; has been used in dogs to treat Pneumocystis infections and Toxoplasma tissue cysts.

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Atovaquone
Systematic (IUPAC) name
trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
Clinical data
Trade names Mepron
AHFS/Drugs.com monograph
MedlinePlus a693003
Pregnancy cat.  ?
Legal status PoM (UK), Rx [US]
Routes oral only
Pharmacokinetic data
Half-life 2.2 to 3.2 days
Identifiers
CAS number 94015-53-9 N
ATC code P01AX06
PubChem CID 74989
DrugBank DB01117
ChemSpider 10482034 YesY
UNII Y883P1Z2LT YesY
KEGG D00236 YesY
ChEBI CHEBI:575568 YesY
ChEMBL CHEMBL1450 YesY
Chemical data
Formula C22H19ClO3 
Mol. mass 366.837 g/mol
SMILES eMolecules & PubChem
 N (what is this?)  (verify)

Atovaquone (alternative spelling: atavaquone) is a chemical compound that belongs to the class of naphthalenes. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of ubiquinone, with antipneumocystic activity. It is manufactured in the US in the liquid form, or oral suspension, under the brand name Mepron.[1]

Contents

Uses

Atovaquone is a medication used to treat or prevent:

  1. Pneumocystis pneumonia (PCP),[2][3] although it is not approved for treatment of severe PCP.
  2. Toxoplasmosis.[4] The medication has antiparasitic and therapeutic effects.
  3. Malaria. 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.[5] Resistance has been observed.[6]
  4. Babesia. It is often used in conjunction with oral azithromycin.[7]

Trimethoprim-sulfamethoxazole (TMP-SMX, Bactrim) is generally considered first line therapy for PCP or toxoplasmosis. However, atovaquone may be used in patients who cannot tolerate, or are allergic to, 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.

Malaria

Atovaquone is available as a combination preparation with proguanil that has been commercially available from GlaxoSmithKline since 2000 as Malarone for the treatment and prevention of malaria. For further details see atovaquone/proguanil.

References

  1. ^ Mepron
  2. ^ Hughes W, Leoung G, Kramer F, et al. (May 1993). "Comparison of atovaquone (566C80) with trimethoprim-sulfamethoxazole to treat Pneumocystis carinii pneumonia in patients with AIDS". N. Engl. J. Med. 328 (21): 1521–7. doi:10.1056/NEJM199305273282103. PMID 8479489. http://content.nejm.org/cgi/pmidlookup?view=short&pmid=8479489&promo=ONFLNS19. 
  3. ^ Dohn MN, Weinberg WG, Torres RA, et al. (August 1994). "Oral atovaquone compared with intravenous pentamidine for Pneumocystis carinii pneumonia in patients with AIDS. Atovaquone Study Group". Ann. Intern. Med. 121 (3): 174–80. PMID 7880228. http://www.annals.org/cgi/pmidlookup?view=long&pmid=7880228. 
  4. ^ 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". J. Antimicrob. Chemother. 50 (6): 981–7. doi:10.1093/jac/dkf251. PMID 12461021. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12461021. 
  5. ^ Malarone: New Malaria Medication With Fewer Side-effects
  6. ^ Färnert A, Lindberg J, Gil P, et al. (March 2003). "Evidence of Plasmodium falciparum malaria resistant to atovaquone and proguanil hydrochloride: case reports". BMJ 326 (7390): 628–9. doi:10.1136/bmj.326.7390.628. PMC 151974. PMID 12649236. http://bmj.com/cgi/pmidlookup?view=long&pmid=12649236. 
  7. ^ Krause PJ, Lepore T, Sikand VK, et al. (November 2000). "Atovaquone and azithromycin for the treatment of babesiosis". N. Engl. J. Med. 343 (20): 1454–8. doi:10.1056/NEJM200011163432004. PMID 11078770. http://content.nejm.org/cgi/content/full/343/20/1454. 

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