A7986
Atovaquone
≥98% (HPLC), powder, anti-protozoal agent
Synonym(s):
Mepron, trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
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About This Item
Empirical Formula (Hill Notation):
C22H19ClO3
CAS Number:
Molecular Weight:
366.84
MDL number:
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
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 in an anti-protozoal mitochondrial electron transport inhibitor. It also functions as an antimalarial and antipneumocystic agent.
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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