General
Preferred name
ATOVAQUONE
Synonyms
Atavaquone ()
Atovaquone D4 ()
Wellvone ()
Mepron ()
566C80 ()
566C ()
NSC-759582 ()
Atovaquone-d4 ()
P&D ID
PD001232
CAS
95233-18-4
2070015-14-2
Tags
natural product
drug
available
Approved by
FDA
First approval
1992
Drug Status
approved
Max Phase
Phase 4
Drug indication
Antipneumocystic
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with .
Note that we have drawn the molecule as specified by the INN record and ChEMBL entry listed on this summary page. The structure for PubChem CID 74989 (link in table below) is shown without specified stereochemistry (InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N). (GtoPdb)
MOA The mechanism of action against Pneumocystis carinii has not been fully elucidated. In Plasmodium species, the site of action appears to be the cytochrome bc1 complex (Complex III). Several metabolic enzymes are linked to the mitochondrial electron transport chain via ubiquinone. Inhibition of electron transport by atovaquone will result in indirect inhibition of these enzymes. The ultimate metabolic effects of such blockade may include inhibition of nucleic acid and ATP synthesis. Atovaquone also has been shown to have good in vitro activity against Toxoplasma gondii.
PHARMACODYNAMICS Atovaquone is a highly lipophilic drug that closely resembles the structure [ubiquinone]. Its inhibitory effect being comparable to ubiquinone, atovaquone can act by selectively affecting mitochondrial electron transport and parallel processes such as ATP and pyrimidine biosynthesis in atovaquone-responsive parasites. Cytochrome bc1 complex (complex III) seems to serve as a highly discriminating molecular target for atovaquone in Plasmodia. There is no significant risk for myelosuppression associated with atovaquone, making this drug a beneficial therapeutic agent for recipients of bone marrow transplantation.
DESCRIPTION Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with .
Note that we have drawn the molecule as specified by the INN record and ChEMBL entry listed on this summary page. The structure for PubChem CID 74989 is shown without specified stereochemistry (InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N).
DESCRIPTION Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with .
Note that we have drawn the molecule as specified by the INN record and ChEMBL entry listed on this summary page. The structure for PubChem CID 74989 shows a different tautomer, with InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N.
DESCRIPTION Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with .
Note that we have drawn the molecule as specified by the INN record and ChEMBL entry listed above. The structure for PubChem CID 74989 shows a different tautomer, with InChi Key BSJMWHQBCZFXBR-UHFFFAOYSA-N.
DESCRIPTION Atovaquone is a synthetic hydroxynaphthoquinone with broad-spectrum antiprotozoal activity. It is an antimalarial drug and used in combination with .
Cell lines
5
Organisms
9
Compound Sets
17
Cayman Chemical Bioactives
23802
28491
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
CHEMBL1450
ChEMBL Drugs
CHEMBL1450
DrugBank
DB01117
DrugBank Approved Drugs
DB01117
DrugCentral
258
DrugCentral Approved Drugs
258
Enamine BioReference Compounds
Guide to Pharmacology
9695
MedChem Express Bioactive Compound Library
HY-13832
NCATS Inxight Approved Drugs
Y883P1Z2LT
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
atovaquone-atavaquone
TargetMol Bioactive Compound Library
T1491
The Spectrum Collection
External IDs
32
Properties
(calculated by RDKit )
Molecular Weight
366.1
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
2
Ring Count
4
Aromatic Ring Count
2
cLogP
5.51
TPSA
54.37
Fraction CSP3
0.27
Chiral centers
0.0
Largest ring
6.0
QED
0.76
Structural alerts
1
quinone_A(370)
[!#6&!#1]=[#6]-1-[#6]=,:[#6]-[#6](=[!#6&!#1])-[#6]=,:[#6]-1
PAINS Family A
Related compounds
Custom attributes
(extracted from source data)
MOA
cytochrome bc1 inhibitor
Dehydrogenase inhibitor
Target
Dihydroorotate dehydrogenase (quinone), mitochondrial
Cytochrome b
DHODH
Parasite
antibiotic
Bacterial
Cytochrome P450
COVID-19,Fungal,Parasite
Pathway
Metabolism
Anti-infection
Metabolic Enzyme/Protease
Source data