Atovaquone
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| 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 | |
| Routes of administration | oral only |
| Pharmacokinetic data | |
| Biological half-life | 2.2 to 3.2 days |
| Identifiers | |
| CAS Number |
95233-18-4  |
| ATC code | P01AX06 |
| PubChem | CID 74989 |
| DrugBank |
DB01117  |
| ChemSpider |
10482034 |
| UNII |
Y883P1Z2LT |
| KEGG |
D00236 |
| ChEBI |
CHEBI:575568 |
| ChEMBL |
CHEMBL1450 |
| Chemical data | |
| Formula | C22H19ClO3 |
| Molar mass | 366.837 g/mol |
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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
Atovaquone is a medication used to treat or prevent:
- For pneumocystis pneumonia (PCP),[2][3] it is used in mild cases, although it is not approved for treatment of severe cases.
- For toxoplasmosis,[4] the medication has antiparasitic and therapeutic effects.
- 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]
- 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
- ↑ Mepron
- ↑ 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.
- ↑ 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. doi:10.7326/0003-4819-121-3-199408010-00003. PMID 7880228.
- ↑ 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.
- ↑ Malarone: New Malaria Medication With Fewer Side-effects
- ↑ 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.
- ↑ 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
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Media related to Atovaquone at Wikimedia Commons - Molecular Basis for Atovaquone Resistance in Pneumocystis jirovecii
- Atovaquone (Meprone)
- British National Formulary
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