Atovaquone: Difference between revisions
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| IUPAC_name = 3-[4-(4-chlorophenyl)cyclohexyl]- 4-hydroxy-naphthalene-1,2-dione | | IUPAC_name = 3-[4-(4-chlorophenyl)cyclohexyl]- 4-hydroxy-naphthalene-1,2-dione | ||
| image = | | image = 220px-Atovaquone_structure_svg.png | ||
| CAS_number = 95233-18-4 | | CAS_number = 95233-18-4 | ||
| ATC_prefix = P01 | | ATC_prefix = P01 | ||
Revision as of 19:58, 22 January 2009
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| Routes of administration | oral only |
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| Elimination half-life | 2.2 to 3.2 days |
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| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C22H19ClO3 |
| Molar mass | 366.837 g/mol |
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1] Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [2] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.
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. Its average wholesale price is about $2.13 per standard 250 mg. tablet.[1] It is also manufactured in the US in the liquid form, or oral suspension, under the brand name Mepron.[2]
Atovaquone is a medication used to treat or prevent:
- Pneumocystis pneumonia (PCP), although it is not approved for treatment of severe PCP.
- Toxoplasmosis. The medication has antiparasitic and therapeutic effects.
- Malaria. It is one of the two components (along with proguanil) in the drug Malarone. Malarone has fewer side effects than mefloquine, but can be more expensive because it's taken daily.[3]
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 only available as a fixed preparation with proguanil that has been commercially available from GlaxoSmithKline since 2000 as Malarone® (sometimes abbreviated A+P). It can be used both to treat and to prevent malaria.
A "standard" tablet of Malarone contains 100 mg of proguanil hydrochloride and 250 mg of atovaquone. A "pediatric" tablet of Malarone contains 25 mg of proguanil hydrochloride and 62.5 mg of atovaquone.
Treatment
The adult treatment dose is four "standard" tablets once a day for three days. In children, the drug is prescribed by body weight:
- 11 to 20 kg: 1 "standard" tablet once daily for 3 days;
- 21 to 30 kg: 2 "standard" tablets once daily for 3 days;
- 31 to 40 kg: 3 "standard" tablets once daily for 3 days;
- 41 kg and above: use adult dose.
Malarone is not licensed for use in children weighing 10 kg or less. The "pediatric" tablets are not used in malaria treatment.
The advice of a specialist should always be sought when starting malaria treatment. Malarone should not be used to treat severe malaria, when an injectable drug (quinine or artesunate in the UK; quinidine in the US) should be used instead.
Prevention
Medical advice should always be taken before choosing a drug for malaria prevention. Because some strains of malaria are resistant, Malarone is not effective for malaria prevention in all parts of the world. It must be taken with a fatty meal or at least some milk to be absorbed adequately.
The adult dose is one "standard" tablet daily starting one or two days before traveling into a malaria-endemic area, and continuing throughout the stay and then for another 7 days after returning from the malarious area.
The child dose is prescribed according to body weight:
- 11–20 kg: 1 "pediatric" tablet once daily;
- 21–30 kg: 2 "pediatric" tablets once daily;
- 31–40 kg: 3 "pediatric" tablets once daily;
- 41 kg and above use adult dose.
The duration of treatment is the same as for adults.
Resistance
Proguanil acts as a mitochondrial sensitiser and synergizes with atovaquone; also, there is a high natural frequency of cytochrome B mutants which leads to a high failure rate if atovaquone is used on its own to treat malaria. Specific mutations (Y268S, Y268C) have been shown to confer resistance in vivo,[4][5][6] but there are other mechanisms of resistance that remain unknown.[7]
References
- ↑ (ATN) Atovaquone (Mepron; 566C80) Approved for Pneumocystis; Drug Development, Activism Success
- ↑ Mepron
- ↑ Malarone: New Malaria Medication With Fewer Side-effects
- ↑ Färnet A, Lindberg J, Gil P; et al. (2003). "Evidence of Plasmodium falciparum malaria resistant to atovaquone and proguoanil hydrochloride: case reports". Brit Med J. 326: 628&ndash, 29.
- ↑ Fivelman QL, Butcher GA, Adagu IS; et al. (2002). "Malarone treatment failure and in-vitro confirmation of resistance of Plasmodium falciparum isolate from Lagos, Nigeria". Malaria J. 1: 1.
- ↑ Schwartz E, Bujanover S, Kain KC (2003). "Genetic confirmation of atovaquone-proguanil-resistant Plasmodium falciparum malaria acquired by a nonimmune traveller to east Africa". Clin Infect Dis. 37: 450&ndash, 51.
- ↑ Wichmann O, Muehlen M, Gruss H; et al. (2004). "Malarone treatment failure not associated with previously described mutations in the cytochrome b gene". Malaria J. 3: 14.
External links
- Molecular Basis for Atovaquone Resistance in Pneumocystis jirovecii
- Atovaquone (Meprone)
- British National Formulary
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