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Proguanil

Proguanil
Systematic (IUPAC) name
1-(4-chlorophenyl)-2-(N'-propan-2-ylcarbamimidoyl) guanidine
Clinical data
Trade names Paludrine
AHFS/Drugs.com
Routes of
administration
Oral
Pharmacokinetic data
Metabolites cycloguanine
Biological half-life ~20 h
Identifiers
CAS Registry Number  Y
ATC code P01
PubChem CID:
DrugBank  Y
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  Y
ChEMBL  Y
Chemical data
Formula C11H16ClN5
Molecular mass 253.731 g/mol
 Y   

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 health system.[3]

Contents

  • Medical uses 1
  • Precautions 2
  • Mechanism 3
  • See also 4
  • References 5
  • External links 6

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. These may come on gradually and may not be immediately attributable to anything in particular.

Mechanism

The active metabolite of the proguanil is cycloguanil, which binds to the DHFR enzyme of the parasite and inhibits the folic acid metabolism. The mechanism for the cyclization of the proguanil to cycloguanil has been recently explored by Bharatam et al.[6]

See also

References

  1. ^ Carrington HC, Crowther AF, Davey DG, Levi AA, Rose FL (1951). "A metabolite of paludrine with high antimalarial activity".  
  2. ^ Crowther AF, Levi AA (1953). "Proguanil, the isolation of a metabolite with high antimalarial activity".  
  3. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  4. ^ Sutherland CJ, Laundy M, Price N, et al. (November 2008). cytochrome b gene are associated with delayed parasite recrudescence in malaria patients treated with atovaquone-proguanill"Plasmodium falciparum"Mutations in the . Malar. J. 7 (1): 240.  
  5. ^ Payen C, Monnin L, Pulce C, Descotes J (December 2008). "Bone marrow aplasia following acute poisoning with chloroquine-proguanil". Clin Toxicol (Phila) 46 (10): 1085–7.  
  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

External links

  • http://healthlink.mcw.edu/article/979237802.html
  • Malarone official website
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