Ligand id: 5535

Name: chloroquine

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 28.16
Molecular weight 319.18
XLogP 4.27
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

No information available.
Summary of Clinical Use
Chloroquine is one of the antimalarials listed in the World Health Organisation's 21st Essential Medicines List (2019), with its recommended use restricted to the prevention and treatment of P. vivax infection in areas where resistance has not yet developed.
It is also used off-label for other conditions/diseases, including treatment of autoimmune disorders (rheumatoid arthritis and lupus erythematosus), as an antiretroviral (HIV-1/AIDS and chikungunya fever) and as a radiosensitizing/chemosensitizing agent benefitting cancer therapies.
Mechanism Of Action and Pharmacodynamic Effects
Chloroquine inhibits ferriprotoporphyrin IX (FP, a heme detoxifying enzyme) found in Plasmodium species. Chloroquine kills the malarial parasite by causing a build up of toxic heme by inhibiting the enzyme that normally converts it to non-toxic hamazion. Chloroquine may also form a complex with FP which is additionally highly toxic to the organism.
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