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Merck

A7986

Sigma-Aldrich

Atovaquone

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C22H19ClO3
Número de CAS:
Peso molecular:
366.84
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

Atovaquone, ≥98% (HPLC)

Quality Level

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


Certificados de análisis (COA)

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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.
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
Nehal Gupta et al.
Pharmaceuticals (Basel, Switzerland), 14(6) (2021-06-03)
Triple-negative breast cancer (TNBC) is considered to be the most aggressive and malignant neoplasm and is highly metastatic in nature. In the current study, we investigated the anti-metastatic potential of atovaquone, a protozoal drug prescribed for Pneumocystis pneumonia. We showed
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
M Cella et al.
Clinical pharmacology and therapeutics, 91(4), 726-733 (2012-03-09)
Concurrent prescription of different drugs is common and is often necessary in many pediatric indications. A randomized concentration-controlled trial (RCCT) is proposed for pediatric studies in which drug combinations are used. The aim of our investigation was to show the

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