Atovaquone

Modify Date: 2024-01-02 17:57:31

Atovaquone Structure
Atovaquone structure
 Common Name Atovaquone
CAS Number 95233-18-4 Molecular Weight 366.837
Density 1.4±0.1 g/cm3 Boiling Point 542.2±50.0 °C at 760 mmHg
Molecular Formula C22H19ClO3 Melting Point 216-2190C
MSDS Chinese USA Flash Point 281.7±30.1 °C

 Use of Atovaquone


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].

 Names

Name atovaquone
Synonym More Synonyms

 Atovaquone 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
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.

 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

 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

cis-atovaquone structure

cis-atovaquone

CAS#:137732-39-9

~85%

Atovaquone Structure

Atovaquone

CAS#:95233-18-4

Literature: WO2010/1378 A1, ; Page/Page column 11 ;
2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone structure

2-(4-(4-Chlorop...

CAS#:94015-53-9

~78%

Atovaquone Structure

Atovaquone

CAS#:95233-18-4

Literature: US2010/137644 A1, ; Page/Page column 3-4 ;
2-chloro-3-(4-(4-chlorophenyl)cyclohexyl)naphthalene-1,4-dione structure

2-chloro-3-(4-(...

CAS#:129719-64-8

~93%

Atovaquone Structure

Atovaquone

CAS#:95233-18-4

Literature: Tetrahedron Letters, , vol. 39, # 42 p. 7629 - 7632
2-(4-(4-Chlorophenyl)cyclohexyl)-3-hydroxy-1,4-naphthoquinone structure

2-(4-(4-Chlorop...

CAS#:94015-53-9

~%

cis-atovaquone structure

cis-atovaquone

CAS#:137732-39-9

Atovaquone Structure

Atovaquone

CAS#:95233-18-4

Literature: WO2012/153162 A1, ; Page/Page column 33 ;
2-Chloro-1,4-naphthoquinone structure

2-Chloro-1,4-na...

CAS#:1010-60-2

~%

Atovaquone Structure

Atovaquone

CAS#:95233-18-4

Literature: Tetrahedron Letters, , vol. 39, # 42 p. 7629 - 7632
cis/trans-1a-(4-(4-chlorophenyl)cyclohexyl)naphtho[2,3-b]oxyrene-2,7(1aH,7aH)-dione structure

cis/trans-1a-(4...

CAS#:1409957-21-6

~74%

Atovaquone Structure

Atovaquone

CAS#:95233-18-4

Literature: WO2013/14486 A1, ; Page/Page column 27; 28 ;
4-(4-Chlorophenyl)cyclohexanecarboxylic acid structure

4-(4-Chlorophen...

CAS#:95233-37-7

~%

Atovaquone Structure

Atovaquone

CAS#:95233-18-4

Literature: Tetrahedron Letters, , vol. 39, # 42 p. 7629 - 7632

 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%

 Articles15

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CYP2C19*17 increases clopidogrel-mediated platelet inhibition but does not alter the pharmacokinetics of the active metabolite of clopidogrel.

Clin. Exp. Pharmacol. Physiol. 41(11) , 870-8, (2014)

The aim of the present study was to determine the impact of CYP2C19*17 on the pharmacokinetics and pharmacodynamics of the active metabolite of clopidogrel and the pharmacokinetics of proguanil. Thus,...

A screen of approved drugs and molecular probes identifies therapeutics with anti-Ebola virus activity.

Sci. Transl. Med. 7 , 290ra89, (2015)

Currently, no approved therapeutics exist to treat or prevent infections induced by Ebola viruses, and recent events have demonstrated an urgent need for rapid discovery of new treatments. Repurposing...

Atovaquone and quinine anti-malarials inhibit ATP binding cassette transporter activity.

Malaria Journal 13 , 359, (2014)

Therapeutic blood plasma concentrations of anti-malarial drugs are essential for successful treatment. Pharmacokinetics of pharmaceutical compounds are dependent of adsorption, distribution, metabolis...

 Synonyms

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)
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