proguanil   Click here for help

GtoPdb Ligand ID: 9676

Synonyms: Bigumal® | chloroguanide | Paludrine®
Approved drug Antimalarial Ligand
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).
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2D Structure
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Physico-chemical Properties
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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
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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)
1. Boggild AK, Parise ME, Lewis LS, Kain KC. (2007)
Atovaquone-proguanil: report from the CDC expert meeting on malaria chemoprophylaxis (II).
Am J Trop Med Hyg, 76 (2): 208-23. [PMID:17297027]
2. Srivastava IK, Vaidya AB. (1999)
A mechanism for the synergistic antimalarial action of atovaquone and proguanil.
Antimicrob Agents Chemother, 43 (6): 1334-9. [PMID:10348748]