Atovaquone

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Atovaquone
Atovaquone Structural Formula V.1.svg
Atovaquone sf.png
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
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
 N (what is this?)  (verify)

Atovaquone (alternative spelling: atavaquone) is a chemical compound that belongs to the class of naphthoquinones. 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]

Uses[edit]

Atovaquone is a medication used to treat or prevent:

  1. For pneumocystis pneumonia (PCP),[2][3] it is used in mild cases, although it is not approved for treatment of severe cases.
  2. For toxoplasmosis,[4] the medication has antiparasitic and therapeutic effects.
  3. For 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. For 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[edit]

Atovaquone, as a combination preparation with proguanil, has been commercially available from GlaxoSmithKline since 2000 as Malarone for the treatment and prevention of malaria.

References[edit]

  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. 
  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. 
  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. 
  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. 
  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. 

External links[edit]