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
Classification
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2000) in combination with atovaquone)
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(1E)-1-[amino-[(4-chlorophenyl)amino]methylidene]-2-propan-2-ylguanidine
International Nonproprietary Names
INN number INN
418 proguanil
Synonyms
Bigumal® | chloroguanide | Paludrine®
Database Links
CAS Registry No. 500-92-5 (source: Scifinder)
ChEBI CHEBI:8455
ChEMBL Ligand CHEMBL1377
DrugBank Ligand DB01131
DrugCentral Ligand 2282
GtoPdb PubChem SID 348353635
PubChem CID 6178111
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Wikipedia Proguanil