Atovaquone

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Atovaquone
Atovaquone Structural Formula V.1.svg
Atovaquone sf.png
Systematic (IUPAC) name
trans-2-[4-(4-chlorophenyl)cyclohexyl]-3-hydroxy-1,4-naphthalenedione
Clinical data
Trade names Mepron
AHFS/Drugs.com monograph
MedlinePlus a693003
Legal status
Routes of
administration		 oral only
Pharmacokinetic data
Biological half-life 2.2 to 3.2 days
Identifiers
CAS Number 95233-18-4 N
ATC code P01AX06 (WHO)
PubChem CID: 74989
DrugBank DB01117 YesY
ChemSpider 10482034 YesY
UNII Y883P1Z2LT YesY
KEGG D00236 YesY
ChEBI CHEBI:575568 YesY
ChEMBL CHEMBL1450 YesY
Chemical data
Formula C22H19ClO3
Molecular mass 366.837 g/mol
  • OC=2C(=O)c1ccccc1C(=O)C=2[C@@H]3CC[C@H](CC3)c4ccc(Cl)cc4
  • 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- YesY
  • Key:KUCQYCKVKVOKAY-CTYIDZIISA-N YesY
 NYesY (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:

  1. For pneumocystis pneumonia (PCP),[2][3] it is used in mild cases, although it is not approved for treatment of severe cases.
  2. For toxoplasmosis,[4] the medication has antiparasitic and therapeutic effects.
  3. 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]
  4. 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

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External links

  1. ↑ Mepron
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Malarone: New Malaria Medication With Fewer Side-effects
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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