Atovaquone

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Atovaquone
Category Others
Catalog number BBF-03966
CAS 95233-18-4
Molecular Weight 366.84
Molecular Formula C22H19ClO3
Purity >98%

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Description

Atovaquone is a medication used to treat or prevent pneumocystis pneumonia, toxoplasmosis, malaria, and babesia.

Specification

Synonyms 566C; 566C80; 566C80 hydroxynaphthoquinone; 566C80, hydroxynaphthoquinone; Atovaquone; hydroxynaphthoquinone 566C80; hydroxynaphthoquinone, 566C80; Mepron; Wellvone
Storage Store at -20°C
IUPAC Name 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxynaphthalene-1,2-dione
Canonical SMILES C1CC(CCC1C2=CC=C(C=C2)Cl)C3=C(C4=CC=CC=C4C(=O)C3=O)O
InChI 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/h1-4,9-13,15,24H,5-8H2
InChI Key BSJMWHQBCZFXBR-UHFFFAOYSA-N
Source Synthetic

Properties

Appearance Yellow to Orange Solid
Application Antipneumocystic
Boiling Point 542.2°C at 760 mmHg
Melting Point >219°C
Density 1.349 g/cm3
Solubility Soluble in tetrahydrofuran, DMSO

Reference Reading

1. The development of quinolone esters as novel antimalarial agents targeting the Plasmodium falciparum bc1 protein complex
Robin Cowley, Suet Leung, Giancarlo A. Biagini* and Paul M. O Neill*. Med. Chem. Commun., 2012, 3,39
The target active site in this study is the Qo site at which ubiquinol is oxidized. The Qo site is located at the interface of two four-helical bundles in the cytochrome b subunit, residing in-between the bL heme and the 2Fe–2S cluster of the iron-sulphur protein when the latter is docked in ISP docking crater. This mainly hydrophobic pocket of approximately 15 A in length, which has the shape of a saddle, is also believed to be the target site a number of pesticides15 as well as that of atovaquone, as evidenced by mutation studies in model organisms, e.g., identification of point mutations in atovaquone/Malarone resistant parasites and molecular modelling studies. The Qo site is also known to be the site of action of the natural bc1 inhibitor stigmatellin 3.
2. The antimalarial drug atovaquone binds to saposin B with comparable affinity to coenzyme Q10
B. P. Huta, A. M. Roberts, E. S. Waters, V. Y. Yu, R. P. Doyle,* M. R. Mehlenbacher and F. Bou-Abdallah*. Med. Chem. Commun.,2014, 5,787–791
Atovaquone (ATO) is a quinone based, orally administered, pharmaceutical effective against several disease-causing protozoa including Plasmodium falciparum (malaria), Pneumocystis jiroveci (pneumonia), and Toxoplasma gondii (toxoplasmosis). The activity of ATO is tracked to its ability to competitively inhibit (Ki, 9 nM) Coenzyme Q10 (CoQ10; ubiquinol) binding to the parasite cytochrome bc1 complex, with a myriad of down-stream consequences to the parasite's mitochondrial respiratory chain.
3. A structure guided drug-discovery approach towards identification of Plasmodium inhibitors
Babita Aneja, Bhumika Kumar, Mohamad Aman Jairajpuri and Mohammad Abid*. RSC Adv.,2016, 6,18364–18406
Noteworthy feature of 183 was its 30-fold more potency than atovaquone against murine malaria. It was found to be $ 20 000-fold more selective for parasite bc1 complex over human enzyme with EC50 value of 0.56 nM thus exhibiting superiority over atovaquone (IC50 = 2.0 nM). Preclinical animal studies on 183 demonstrated nonlinear pharmacokinetics i.e. good to excellent oral bioavailability at low doses needed for therapeutic effect but fell off rapidly at higher doses. Further studies need to be carried out to identify clinical formulation in order to improve exposure at higher doses. Compound 183 displayed potential that might be carried forward for clinical studies.

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