proguanil   

GtoPdb Ligand ID: 9676

Synonyms: Bigumal® | chloroguanide | Paludrine®
proguanil is an approved drug (FDA (2000) in combination with atovaquone)
Compound class: Synthetic organic
Comment: Proguanil is a biguanide derivative that, once administered, is converted to the active metabolite cycloguanil. It is an antimalarial drug, used in combination with atovaquone or with chloroquine.
The marketed formulations contain proguanil hydrochloride (PubChem CID 9570076).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 88.79
Molecular weight 253.11
XLogP 1.84
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(N=C(N=C(Nc1ccc(cc1)Cl)N)N)C
Isomeric SMILES CC(N=C(/N=C(/Nc1ccc(cc1)Cl)\N)N)C
InChI InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)
InChI Key SSOLNOMRVKKSON-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Proguanil is used in combination with atovaquone in both the treatment of uncomplicated malaria caused by P. falciparum and in malaria prophylaxis [1].
Proguanil is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
Mechanism Of Action and Pharmacodynamic Effects
Cycloguanil, the active metabolite of proguanil, is an inhibitor of Plasmodium dihydrofolate reductase (DHFR). Proguanil has a different mechanism of action when used in combination with atovaquone, with the prodrug having synergistic activity, leading to enhanced collapse of the mitochondrial membrane potential [2].
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