A7986
Atovaquone
≥98% (HPLC), powder, anti-protozoal agent
Synonyme(s) :
Mepron, trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
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A propos de cet article
Formule empirique (notation de Hill) :
C22H19ClO3
Numéro CAS:
Poids moléculaire :
366.84
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Laissez-nous vous aiderNom du produit
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.
Classe de stockage
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.
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
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