Atovaquone

Atovaquone
Clinical data
Trade names	Mepron
AHFS/Drugs.com	Monograph
MedlinePlus	a693003
Routes of; administration	oral only
ATC code	P01AX06 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Elimination half-life	2.2 to 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	366.837 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 (alternative spelling: atavaquone) is a chemical compound that belongs to the class of naphthoquinones. Atovaquone is a hydroxy-1,4-naphthoquinone, an analog of ubiquinone, with antipneumocystic activity. It is manufactured in the US in the liquid form, or oral suspension, under the brand name Mepron.^[1]

Uses

Atovaquone is a medication used to treat or prevent:

For pneumocystis pneumonia (PCP),^[2]^[3] it is used in mild cases, although it is not approved for treatment of severe cases.
For toxoplasmosis,^[4] the medication has antiparasitic and therapeutic effects.
For malaria, it is one of the two components (along with proguanil) in the drug Malarone. Malarone has fewer side effects and is more expensive than mefloquine.^[5] Resistance has been observed.^[6]
For babesia, it is often used in conjunction with oral azithromycin.^[7]

Trimethoprim-sulfamethoxazole (TMP-SMX, Bactrim) is generally considered first-line therapy for PCP or toxoplasmosis. However, atovaquone may be used in patients who cannot tolerate, or are allergic to, sulfonamide medications such as TMP-SMX. In addition, atovaquone has the advantage of not causing myelosuppression, which is an important issue in patients who have undergone bone marrow transplantation.

Malaria

Atovaquone, as a combination preparation with proguanil, has been commercially available from GlaxoSmithKline since 2000 as Malarone for the treatment and prevention of malaria.

References

^ Mepron
^ Hughes W, Leoung G, Kramer F; et al. (May 1993). "Comparison of atovaquone (566C80) with trimethoprim-sulfamethoxazole to treat Pneumocystis carinii pneumonia in patients with AIDS". N. Engl. J. Med. 328 (21): 1521–7. doi:10.1056/NEJM199305273282103. PMID 8479489.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Dohn MN, Weinberg WG, Torres RA; et al. (August 1994). "Oral atovaquone compared with intravenous pentamidine for Pneumocystis carinii pneumonia in patients with AIDS. Atovaquone Study Group". Ann. Intern. Med. 121 (3): 174–80. doi:10.7326/0003-4819-121-3-199408010-00003. PMID 7880228.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Djurković-Djaković O, Milenković V, Nikolić A, Bobić B, Grujić J (December 2002). "Efficacy of atovaquone combined with clindamycin against murine infection with a cystogenic (Me49) strain of Toxoplasma gondii". J. Antimicrob. Chemother. 50 (6): 981–7. doi:10.1093/jac/dkf251. PMID 12461021.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Malarone: New Malaria Medication With Fewer Side-effects
^ Färnert A, Lindberg J, Gil P; et al. (March 2003). "Evidence of Plasmodium falciparum malaria resistant to atovaquone and proguanil hydrochloride: case reports". BMJ. 326 (7390): 628–9. doi:10.1136/bmj.326.7390.628. PMC 151974. PMID 12649236.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Krause PJ, Lepore T, Sikand VK; et al. (November 2000). "Atovaquone and azithromycin for the treatment of babesiosis". N. Engl. J. Med. 343 (20): 1454–8. doi:10.1056/NEJM200011163432004. PMID 11078770.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

Media related to Atovaquone at Wikimedia Commons
Molecular Basis for Atovaquone Resistance in Pneumocystis jirovecii
Atovaquone (Meprone)
British National Formulary

[1] Mepron

[pmid8479489-2] Hughes W, Leoung G, Kramer F; et al. (May 1993). "Comparison of atovaquone (566C80) with trimethoprim-sulfamethoxazole to treat Pneumocystis carinii pneumonia in patients with AIDS". N. Engl. J. Med. 328 (21): 1521–7. doi:10.1056/NEJM199305273282103. PMID 8479489.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[pmid7880228-3] Dohn MN, Weinberg WG, Torres RA; et al. (August 1994). "Oral atovaquone compared with intravenous pentamidine for Pneumocystis carinii pneumonia in patients with AIDS. Atovaquone Study Group". Ann. Intern. Med. 121 (3): 174–80. doi:10.7326/0003-4819-121-3-199408010-00003. PMID 7880228.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[pmid12461021-4] Djurković-Djaković O, Milenković V, Nikolić A, Bobić B, Grujić J (December 2002). "Efficacy of atovaquone combined with clindamycin against murine infection with a cystogenic (Me49) strain of Toxoplasma gondii". J. Antimicrob. Chemother. 50 (6): 981–7. doi:10.1093/jac/dkf251. PMID 12461021.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[5] Malarone: New Malaria Medication With Fewer Side-effects

[pmid12649236-6] Färnert A, Lindberg J, Gil P; et al. (March 2003). "Evidence of Plasmodium falciparum malaria resistant to atovaquone and proguanil hydrochloride: case reports". BMJ. 326 (7390): 628–9. doi:10.1136/bmj.326.7390.628. PMC 151974. PMID 12649236.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[7] Krause PJ, Lepore T, Sikand VK; et al. (November 2000). "Atovaquone and azithromycin for the treatment of babesiosis". N. Engl. J. Med. 343 (20): 1454–8. doi:10.1056/NEJM200011163432004. PMID 11078770.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1]

[2]

[3]

[4]

[5]

[6]

[7]