Atovaquone

Names

[ Name ]:
Atovaquone

[Synonym ]:
2-Propanol,1-[2-(4-methyl-1,3-dioxolan-2-yl)ethoxy]
2-[trans-4-(4'-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
1,2-Naphthalenedione, 3-[4-(4-chlorophenyl)cyclohexyl]-4-hydroxy-
MFCD00889188
3-(4-(4-chlorophenyl)cyclohexyl)-4-hydroxy-naphthalene-1,2-dione
trans-2-[2-(2-hydroxypropoxy)-ethyl]-4-methyl-1,3-dioxolane
Atovaquone
trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthoquinone
3-[4-(4-Chlorophenyl)cyclohexyl]-4-hydroxy-1,2-naphthalenedione
2-(trans-4-(4-chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthalenedione
(trans-2-hydroxy-3-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone)

Biological Activity

[Description]:

Atovaquone is a medication used to treat or prevent for pneumocystis pneumonia, toxoplasmosis, malaria, and babesia.Target: AntiparasiticAtovaquone (atavaquone) is a chemical compound that belongs to the class of naphthalenes. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of ubiquinone, with antipneumocystic activity [1]. Atovaquone is an anti-protozoal mitochondrial electron transport inhibitor; Antimalarial; Antipneumocystic, and has also been used to treat toxoplasmosis. It acts by inhibiting the cytochrome bc(1) complex via interactions with the Rieske iron-sulfur protein and cytochrome b in the ubiquinol oxidation pocket [2]. Atovaquone is a unique naphthoquinone with broad-spectrum antiprotozoal activity. It is effective for the treatment and prevention of Pneumocystis carinii pneumonia (PCP), it is effective in combination with proguanil for the treatment and prevention of malaria, and it is effective in combination with azithromycin for the treatment of babesiosis [3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[References]

[1]. Looareesuwan, S., et al., Clinical studies of atovaquone, alone or in combination with other antimalarial drugs, for treatment of acute uncomplicated malaria in Thailand. Am J Trop Med Hyg, 1996. 54(1): p. 62-6.

[2]. Kessl, J.J., et al., Molecular basis for atovaquone binding to the cytochrome bc1 complex. J Biol Chem, 2003. 278(33): p. 31312-8.

[3]. Baggish, A.L. and D.R. Hill, Antiparasitic agent atovaquone. Antimicrobial agents and chemotherapy, 2002. 46(5): p. 1163-1173.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
542.2±50.0 °C at 760 mmHg

[ Melting Point ]:
216-2190C

[ Molecular Formula ]:
C₂₂H₁₉ClO₃

[ Molecular Weight ]:
366.837

[ Flash Point ]:
281.7±30.1 °C

[ Exact Mass ]:
366.102264

[ PSA ]:
54.37000

[ LogP ]:
5.86

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.653

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Statements ]:
H413

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50/53

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
QJ5616500

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914700090

[ Summary ]:
HS: 2914700090 halogenated, sulphonated, nitrated or nitrosated derivatives of ketones and quinones, whether or not with other oxygen function Tax rebate rate:9.0% Supervision conditions:none VAT:17.0% MFN tariff:5.5% General tariff:30.0%

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