Structure via PubChem · Public domain (PubChem)
atovaquone
Sign in to saveAlso known as Acuvel, 2-(trans-4-(P-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone, Mepron, Wellvone, 566C, 566C80
Atovaquone, sold under the brand name Mepron, is an naphthoquinone antiprotozoal medication used in the prevention and treatment Pneumocystis jirovecii pneumonia (PCP), and malaria (in combination with proguanil), as well as for treatment of babesiosis (in combination with azithromycin).
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 458780973
- Drug.image
- Atovaquone Structural Formula V.1.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 215
- Drug.image2
- Atovaquone-from-xtal-Mercury-3D-bs.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Mepron
- Drug.MedlinePlus
- a693003
- Drug.pregnancy_US
- C
- Drug.legal_US
- Rx-only
- Drug.legal_UK
- POM
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- P01
- Drug.ATC_suffix
- AX06
- Drug.elimination_half life
- 2.2–3.2 days
- Drug.CAS_number
- 95233-18-4
via Wikipedia infobox
Chemical data
- Formula
- C22H19ClO3
- Molecular weight
- 366.8 g/mol
- IUPAC name
- 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
- SMILES
- C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
- InChIKey
- BSJMWHQBCZFXBR-UHFFFAOYSA-N
- XLogP
- 5.2
- Polar surface area
- 54.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
1,705 papersvia PubMed
~7 min read
Encyclopedic overview
17 sectionsContents
- Medical uses
- Pneumocystis pneumonia
- Malaria
- Chemoprophylaxis
- Treatment
- Resistance
- Adverse effects
- Pharmacology
- Pharmacodynamics
- Synergism
- Interactions
- Research
- COVID-19
- Veterinary use
- References
- Further reading
- External links
Atovaquone, sold under the brand name Mepron, is an naphthoquinone antiprotozoal medication used in the prevention and treatment Pneumocystis jirovecii pneumonia (PCP), and malaria (in combination with proguanil), as well as for treatment of babesiosis (in combination with azithromycin).
Atovaquone is an analogue of ubiquinone (coenzyme Q10) and exerts its pharmaceutical effects by binding to the ubiquinone binding site on the parasitic mitochondrial cytochrome bc1 complex, thus inhibiting a step of protozoal pyrimidine synthesis.
Excerpted from Wikipedia’s “atovaquone” article, available under the CC BY-SA 4.0 licence.