Proguanil

Proguanil, also known as chlorguanide and chloroguanide, is a medication used to treat and prevent malaria. It is often used together with chloroquine or atovaquone. When used with chloroquine the combination will treat mild chloroquine resistant malaria. It is taken by mouth.

Proguanil
Clinical data
Trade namesPaludrine, others
Other nameschlorguanide, chloroguanide
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		By mouth (tablets)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding75%
MetabolismBy liver (CYP2C19)
Metabolitescycloguanil and 4-chlorophenylbiguanide
Elimination half-life12–21 hours
Identifiers
  • 1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.196
Chemical and physical data
FormulaC11H16ClN5
Molar mass253.73 g·mol−1
3D model (JSmol)
Melting point129 °C (264 °F)
  • Clc1ccc(NC(=N/C(=N/C(C)C)N)N)cc1
  • 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) Y
  • Key:SSOLNOMRVKKSON-UHFFFAOYSA-N Y
  (verify)

Side effects include diarrhea, constipation, skin rashes, hair loss, and itchiness. Because malaria tends to be more severe in pregnancy, the benefit typically outweighs the risk. If used during pregnancy it should be taken with folate. It is likely safe for use during breastfeeding. Proguanil is converted by the liver to its active metabolite, cycloguanil.

It is on the World Health Organization's List of Essential Medicines. In the United States and Canada it is only available in combination as atovaquone/proguanil.

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