Proguanil

Proguanil
Clinical data
Trade namesPaludrine, others
Other nameschlorguanide, chloroguanide[1]
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		By mouth
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[2]
Identifiers
IUPAC name
  • 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)
SMILES
  • Clc1ccc(NC(=N/C(=N/C(C)C)N)N)cc1
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) Y
  • Key:SSOLNOMRVKKSON-UHFFFAOYSA-N Y
  (verify)

Proguanil, also known as chlorguanide and chloroguanide, is a medication used to treat and prevent malaria.[3][4] It is often used together with chloroquine or atovaquone.[4][3] When used with chloroquine the combination will treat mild chloroquine resistant malaria.[3] It is taken by mouth.[4]

Side effects include diarrhea, constipation, skin rashes, hair loss, and itchiness.[3] Because malaria tends to be more severe in pregnancy, the benefit typically outweighs the risk.[3] If used during pregnancy it should be taken with folate.[3] It is likely safe for use during breastfeeding.[3] Proguanil is converted by the liver to its active metabolite, cycloguanil.[4]

It is on the World Health Organization's List of Essential Medicines.[5] In the United States and Canada it is only available in combination as atovaquone/proguanil.[6]

  1. ^ Mehlhorn H (2008). "Proguanil". Encyclopedia of Parasitology: A-M. Springer Science & Business Media. p. 388. ISBN 9783540489948. Archived from the original on 20 December 2016.
  2. ^ "Malarone (atovaquone/proguanil) Tablets, Pediatric Tablets. Full Prescribing Information" (PDF). GlaxoSmithKline. Research Triangle Park, NC 27709. Archived (PDF) from the original on 20 September 2016. Retrieved 14 July 2016.
  3. ^ a b c d e f g World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 199, 203. hdl:10665/44053. ISBN 9789241547659.
  4. ^ a b c d "Atovaquone and Proguanil Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  5. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  6. ^ "Proguanil". www.medscape.com. Medscape. Archived from the original on 9 November 2016. Retrieved 8 November 2016.
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