An antiprotozoal agent
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Labeled Version(s)
28491Atovaquone-d4
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Atovaquone

Item No. 23802

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[trans-4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
CAS Number
95233-18-4
Synonyms
  • BW 566C
  • BW 556C-80
Molecular Formula
C22H19ClO3
Formula Weight
366.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMF:PBS (pH 7.2) (1:5): 0.16 mg/mlDMSO: 1 mg/mlEthanol: slightly soluble
λmax
203, 220, 253, 284
SMILES
O=C1C([C@@H]2CC[C@@H](C3=CC=C(Cl)C=C3)CC2)=C(O)C(C4=CC=CC=C41)=O
InChi Code
InChI=1S/C22H19ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-4,9-13,15,26H,5-8H2/t13-,15-
InChi Key
KUCQYCKVKVOKAY-CTYIDZIISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Atovaquone is a broad-spectrum antiprotozoal agent that is active against Plasmodium, Toxoplasma, and Babesia, among other protozoa.1 It inhibits complex III activity on dihydroorotate in isolated P. falciparum and P. yoelii mitochondria more potently than in rat liver mitochondria (EC50s = 0.95, 0.94, and 510 nM, respectively) and depolarizes the mitochondrial membrane in P. yoelii-infected mouse erythrocytes (EC50 = 260 nM).2,3 Atovaquone also inhibits transport mediated by human breast cancer resistance protein (BCRP) and P-glycoprotein in membrane vesicles (IC50s = 0.23 and 6.8 μM, respectively).4 It inhibits the growth of T. gondii in MRC-5 human lung fibroblasts in vitro (IC50 = ~64 nM) and increases mean survival of T. gondii-infected mice from 5.5 to 21.2 days when administered at a dose of 100 mg/kg per day.5 Formulations containing atovaquone have been used in the treatment of Pneumocystis pneumonia and toxoplasmosis as well as in combination with proguanil in the treatment of malaria and babesiosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kessl, J.J., Lange, B.B., Merbitz-Zahradnik, T., et al. Molecular basis for atovaquone binding to the cytochrome bc1 complex. The Journal of Biological Chemisty 278(33), 31312-31318 (2003).

    2. Fry, M., and Pudney, M. Site of action of the antimalarial hydroxynaphthoquinone, 2-[trans-4-(4'-chlorophenyl) cyclohexyl]-3-hydroxy-1,4-naphthoquinone (566C80). Biochem. Pharmacol. 43(7), 1545-1553 (1992).

    3. Srivastava, I.K., Rottenberg, H., and Vaidya, A.B. Atovaquone, a broad spectrum antiparasitic drug, collapses mitochondrial membrane potential in a malarial parasite. The Journal of Biological Chemisty 272(7), 3961-3966 (1997).

    4. Rijpma, S.R., van den Heuvel, J.J., van der Velden, M., et al. Atovaquone and quinine anti-malarials inhibit ATP binding cassette transporter activity. Malar. J. 13, 359 (2014).

    5. Romand, S., Pudney, M., and Derouin, F. In vitro and in vivo activities of the hydroxynaphthoquinone atovaquone alone or combined with pyrimethamine, sulfadiazine, clarithromycin, or minocycline against Toxoplasma gondii. Antimicrob. Agents Chemother. 37(11), 2371-2378 (1993).