Proguanil

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Proguanil
File:Proguanil Structural Formulae.png
File:Proguanil sf.png
Systematic (IUPAC) name
1-(4-chlorophenyl)-2-(N'-propan-2-ylcarbamimidoyl) guanidine
Clinical data
Trade names Paludrine
AHFS/Drugs.com Micromedex Detailed Consumer Information
Routes of
administration		 Oral
Pharmacokinetic data
Metabolites cycloguanine
Biological half-life ~20 h
Identifiers
CAS Number 500-92-5 YesY
ATC code P01BB01 (WHO)
PubChem CID: 4923
DrugBank DB01131 YesY
ChemSpider 4754 YesY
UNII S61K3P7B2V YesY
KEGG D08428 YesY
ChEBI CHEBI:8455 YesY
ChEMBL CHEMBL1377 YesY
Chemical data
Formula C11H16ClN5
Molecular mass 253.731 g/mol
  • 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) YesY
  • Key:SSOLNOMRVKKSON-UHFFFAOYSA-N YesY
  (verify)

Proguanil (chlorguanide, chloroguanide) is a prophylactic antimalarial drug.[1][2] When taken, it is converted to the active metabolite cycloguanil. Proguanil is effective against sporozoites. Proguanil hydrochloride is marketed as Paludrine by AstraZeneca.

It has been used for malarial prophylaxis in children with sickle cell disease living in malaria-endemic areas for many years.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[3]

Medical uses

Proguanil is usually taken in combination with another antimalarial drug, such as atovaquone[4] (e.g. in the combination Malarone) or chloroquine.[5]

Malarone has fewer side effects than mefloquine, but can be more expensive because it is taken daily.

Proguanil is taken with atovaquone for chloroquine-resistant and multidrug resistant strains of P. falciparum and P. vivax. Proguanil combined with atovaquone is sold under the tradename Malarone (GlaxoSmithKline).

Precautions

General precautions regarding proguanil involve watching out for feelings of sullenness and anxiety to a level outside the ordinary, when taking it over a period of several months.[citation needed] These may come on gradually and may not be immediately attributable to anything in particular.

Mechanism

One mode of action involves cyclization to form cycloguanil,[6] which binds to the DHFR enzyme of the parasite and inhibits the folic acid metabolism. However, proguanil itself may have an alternative mechanism of antimalarial action besides dihydrofolate reductase inhibition.[7]

See also

References

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External links

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  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Importance of cytochromes in cyclization reactions: Quantum chemical study on a model reaction of proguanil to cycloguanil. Minhajul Arfeen, Dhilon S Patel, Sheenu Abbat, Nikhil Taxak, Prasad V Bharatam, Journal of Computational Chemistry, 2014, 35, 28, 2047-2055
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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