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A7986

Sigma-Aldrich

Atovaquone

≥98% (HPLC), powder, anti-protozoal agent

Synonyma:

Mepron, trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione

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About This Item

Empirický vzorec (Hillův zápis):
C22H19ClO3
Číslo CAS:
95233-18-4
Molekulová hmotnost:
366.84
UNSPSC Code:
12352200
PubChem Substance ID:
329770944
NACRES:
NA.77

product name

Atovaquone, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: >10 mg/mL

originator

GlaxoSmithKline

storage temp.

−20°C

SMILES string

OC1=C([C@H]2CC[C@@H](CC2)c3ccc(Cl)cc3)C(=O)c4ccccc4C1=O

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

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Application

Atovaquone inhibits the cytochrome bc(1) complex via interactions with the Rieske iron-sulfur protein and cytochrome b in the ubiquinol oxidation pocket. In addition to its use as a treatment for toxoplasmosis, atovaquone has antimalarial properties and prevents pneumocystis pneumonia post-renal transplant.

Biochem/physiol Actions

Atovaquone is an anti-protozoal mitochondrial electron transport inhibitor; Antimalarial; Antipneumocystic, and has also been used to treat toxoplasmosis. It is an analog of protozoan mitochondrial protein ubiquinone, and acts by inhibiting the cytochrome bc(1) complex via interactions with the Rieske iron-sulfur protein and cytochrome b in the ubiquinol oxidation pocket.

Features and Benefits

This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

Steven Gabardi et al.
Clinical transplantation, 26(3), E184-E190 (2012-04-11)
Pneumocystis pneumonia (PCP) is associated with significant morbidity and mortality in renal transplant recipients (RTR). Trimethoprim-sulfamethoxazole (TMP-SMZ) is considered the prophylactic agent-of-choice. Some patients require an alternative owing to TMP-SMZ intolerance. This is the first evaluation of full-dose atovaquone vs.
Zehua Song et al.
Antimicrobial agents and chemotherapy, 59(7), 4053-4058 (2015-04-29)
The bc1 complex is central to mitochondrial bioenergetics and the target of the antimalarial drug atovaquone that binds in the quinol oxidation (Qo) site of the complex. Structural analysis has shown that the Qo site residue Y279 (Y268 in Plasmodium
Mikio Kimura et al.
Parasitology international, 61(3), 466-469 (2012-04-10)
Malaria remains an important health risk among travelers to tropical/subtropical regions. However, in Japan, only 2 antimalarials are licensed for clinical use - oral quinine and mefloquine. The Research Group on Chemotherapy of Tropical Diseases introduced atovaquone-proguanil in 1999, and
Kai J Rogers et al.
Cell reports, 30(12), 4041-4051 (2020-03-27)
During the 2013-2016 Ebola virus (EBOV) epidemic, a significant number of patients admitted to Ebola treatment units were co-infected with Plasmodium falciparum, a predominant agent of malaria. However, there is no consensus on how malaria impacts EBOV infection. The effect
Zehua Song et al.
Biochimica et biophysica acta, 1847(12), 1487-1494 (2015-08-25)
The respiratory chain bc1 complex is central to mitochondrial bioenergetics and the target of antiprotozoals. We characterized a modified yeast bc1 complex that more closely resemble Plasmodium falciparum enzyme. The mutant version was generated by replacing ten cytochrome b Qo
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