Atovaquone

Atovaquone

Atovaquone
Systematic (IUPAC) name
trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
Clinical data
Trade names Mepron
AHFS/Drugs.com
MedlinePlus
Legal status
Routes of
administration
oral only
Pharmacokinetic data
Biological half-life 2.2 to 3.2 days
Identifiers
CAS Registry Number  N
ATC code P01
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  Y
ChEMBL  Y
Chemical data
Formula C22H19ClO3
Molecular mass 366.837 g/mol
 N   

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]

Contents

  • Uses 1
  • Malaria 2
  • References 3
  • External links 4

Uses

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, 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.

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.

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.  
  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.  
  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.  
  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.  
  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.  

External links

  • Pneumocystis jiroveciiMolecular Basis for Atovaquone Resistance in
  • Atovaquone (Meprone)
  • British National Formulary