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Atovaquone (also called atavaquone) is a hydroxynaphthoquinone based antiprotozoal and antimicrobial medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia. Atovaquone 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. Atovaquone is an anti-protozoal mitochondrial electron transport inhibitor; Antimalarial; Antipneumocystic, and has also been used to treat toxoplasmosis. It acts by inhibiting the cytochrome bc(1) complex via interactions with the Rieske iron-sulfur protein and cytochrome b in the ubiquinol oxidation pocket.
Physicochemical Properties
| Molecular Formula | C22H19CLO3 |
| Molecular Weight | 366.84 |
| Exact Mass | 366.102 |
| Elemental Analysis | C, 72.03; H, 5.22; Cl, 9.66; O, 13.08 |
| CAS # | 95233-18-4 |
| Related CAS # | Atovaquone-d4;2070015-14-2;Atovaquone-d5;1329792-63-3;cis-Atovaquone-d4 |
| PubChem CID | 74989 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 542.2±50.0 °C at 760 mmHg |
| Melting Point | 216-2190C |
| Flash Point | 281.7±30.1 °C |
| Vapour Pressure | 0.0±1.5 mmHg at 25°C |
| Index of Refraction | 1.653 |
| LogP | 5.86 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 26 |
| Complexity | 595 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C1C2C=CC=CC=2C(=O)C(O)=C1[C@@H]1CC[C@@H](C2C=CC(Cl)=CC=2)CC1 |
| InChi Key | KUCQYCKVKVOKAY-CTYIDZIISA-N |
| 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- |
| Chemical Name | trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione |
| Synonyms | 566C; 566C80; 566C80 hydroxynaphthoquinone; 566C80, hydroxynaphthoquinone; Atovaquone; atovaquone GlaxoSmithKline brand; compound 566; Glaxo Wellcome brand of atovaquone; GlaxoSmithKline brand of atovaquone; hydroxynaphthoquinone 566C80; hydroxynaphthoquinone, 566C80; Mepron; Wellvone |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
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| References | Am J Trop Med Hyg.1996 Jan;54(1):62-6;J Biol Chem.2003 Aug 15;278(33):31312-8;Antimicrob Agents Chemother. 2002 May; 46(5): 1163–1173. | ||
| Additional Infomation |
Atovaquone is a naphthoquinone compound having a 4-(4-chlorophenyl)cyclohexyl group at the 2-position and a hydroxy substituent at the 3-position. It has a role as an antimalarial, an antifungal agent, an EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor, an EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor and an EC 1.10.2.2 (quinol--cytochrome-c reductase) inhibitor. It is a member of monochlorobenzenes and a hydroxy-1,4-naphthoquinone. Atovaquone is an Antimalarial and Antiprotozoal. A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols. See also: Atovaquone (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO :8.33 ~ 11 mg/mL ( 22.71 ~29.98 mM ) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 0.83 mg/mL (2.26 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.83 mg/mL (2.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 3: 5% DMSO + Corn oil: 0.5mg/ml (1.36mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7260 mL | 13.6299 mL | 27.2598 mL | |
| 5 mM | 0.5452 mL | 2.7260 mL | 5.4520 mL | |
| 10 mM | 0.2726 mL | 1.3630 mL | 2.7260 mL |