Atovaquone

Atovaquone
Clinical data
Trade names	Mepron
AHFS/Drugs.com	Monograph
MedlinePlus	a693003
Routes of; administration	By mouth
ATC code	P01AX06 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Elimination half-life	2.2–3.2 days
Identifiers
	IUPAC name trans-2-[4-(4-Chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione;
CAS Number	95233-18-4 ;
PubChem CID	74989;
DrugBank	DB01117 ;
ChemSpider	10482034 ;
UNII	Y883P1Z2LT;
KEGG	D00236 ;
ChEBI	CHEBI:575568 ;
ChEMBL	ChEMBL1450 ;
CompTox Dashboard (EPA)	DTXSID7022629 ;
ECHA InfoCard	100.158.738
Chemical and physical data
Formula	C22H19ClO3
Molar mass	366.84 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	216 to 219 °C (421 to 426 °F)
	SMILES OC=2C(=O)c1ccccc1C(=O)C=2[C@@H]3CC[C@H](CC3)c4ccc(Cl)cc4;
	InChI 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- ; Key:KUCQYCKVKVOKAY-CTYIDZIISA-N ;
	(what is this?) (verify)

Atovaquone, sold under the brand name Mepron,^[2] is an naphthoquinone antiprotozoal^[3] medication used in the prevention and treatment Pneumocystis jirovecii pneumonia (PCP),^[2] and malaria (in combination with proguanil), as well as for treatment of babesiosis (in combination with azithromycin).^[4]

Atovaquone is an analogue of ubiquinone (coenzyme Q10) and exerts its pharmaceutical effects by binding to the ubiquinone binding site on the parasitic mitochondrial cytochrome bc1 complex, thus inhibiting a step of protozoal pyrimidine synthesis.^[5]

Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of both ubiquinone and lawsone.

^ "Wellvone 750mg/5ml oral suspension - Summary of Product Characteristics (SmPC)". (emc). 28 November 2019. Retrieved 18 September 2020.
^ ^a ^b "Atovaquone Oral SUSPENSION- atovaquone suspension". DailyMed. 10 December 2019. Retrieved 18 September 2020.
^ Ritter JM, Flower R, Henderson G, Loke YK, MacEwan D, Rang HP (2020). Rang & Dale's Pharmacology (9th ed.). Edinburgh London New York: Elsevier. pp. 704–705. ISBN 978-0-7020-7448-6.
^ Baggish AL, Hill DR (May 2002). "Antiparasitic agent atovaquone". Antimicrobial Agents and Chemotherapy. 46 (5): 1163–1173. doi:10.1128/AAC.46.5.1163-1173.2002. ISSN 0066-4804. PMC 127192. PMID 11959541.
^ Cite error: The named reference Brunton_2023 was invoked but never defined (see the help page).

[1] "Wellvone 750mg/5ml oral suspension - Summary of Product Characteristics (SmPC)". (emc). 28 November 2019. Retrieved 18 September 2020.

[DailyMed-2] "Atovaquone Oral SUSPENSION- atovaquone suspension". DailyMed. 10 December 2019. Retrieved 18 September 2020.

[Ritter_2020-3] Ritter JM, Flower R, Henderson G, Loke YK, MacEwan D, Rang HP (2020). Rang & Dale's Pharmacology (9th ed.). Edinburgh London New York: Elsevier. pp. 704–705. ISBN 978-0-7020-7448-6.

[4] Baggish AL, Hill DR (May 2002). "Antiparasitic agent atovaquone". Antimicrobial Agents and Chemotherapy. 46 (5): 1163–1173. doi:10.1128/AAC.46.5.1163-1173.2002. ISSN 0066-4804. PMC 127192. PMID 11959541.

[Brunton_2023-5] Cite error: The named reference Brunton_2023 was invoked but never defined (see the help page).

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Atovaquone

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