Proguanil

Proguanil
Proguanil
Systematic (IUPAC) name
1-(4-chlorophenyl)-2-(N'-propan-2-ylcarbamimidoyl) guanidine
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat.  ?
Legal status  ?
Routes Oral
Pharmacokinetic data
Half-life ~20 h
Identifiers
CAS number 500-92-5 YesY
ATC code P01BB01
PubChem CID 4923
DrugBank APRD00188
ChemSpider 4754 YesY
UNII S61K3P7B2V YesY
KEGG D08428 YesY
ChEBI CHEBI:8455 N
ChEMBL CHEMBL1377 YesY
Chemical data
Formula C11H16ClN5 
Mol. mass 253.731 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Proguanil (chlorguanide, chloroguanide) is a prophylactic antimalarial drug.

Proguanil is effective against sporozoites.

Proguanil hydrochloride is marketed as Paludrine by AstraZeneca.

Contents

Mechanism

It works by stopping the malaria parasite, Plasmodium falciparum and Plasmodium vivax, from reproducing once it is in the red blood cells.

It does this by inhibiting the enzyme dihydrofolate reductase, which catalyzes the formation of tetrahydrofolate, the main one carbon unit carrier in our body, required for dTMP and purine base synthesis.

Combinations

Proguanil is usually taken in combination with another anti-malarial drug such as atovaquone[1] (e.g., in the drug Malarone) or chloroquine.[2]

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 precaution regarding Proguanil involves watching out for feelings of sullenness and anxiety to a level that is outside the ordinary, when taking over a period of several months.[citation needed] These may come on gradually and may not be immediately attributable to anything in particular.

References

  1. ^ Sutherland CJ, Laundy M, Price N, et al. (November 2008). "Mutations in the Plasmodium falciparum cytochrome b gene are associated with delayed parasite recrudescence in malaria patients treated with atovaquone-proguanill". Malar. J. 7 (1): 240. doi:10.1186/1475-2875-7-240. PMC 2640403. PMID 19021900. http://www.malariajournal.com/content/7/1/240. 
  2. ^ 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. doi:10.1080/15563650601182925. PMID 19065311. http://www.informaworld.com/openurl?genre=article&doi=10.1080/15563650601182925&magic=pubmed%7C%7C1B69BA326FFE69C3F0A8F227DF8201D0. 

External links

v · d · eAntiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)
Alveo-
late
Individual
agents
Other
DHFR inhibitors
(antifols)
2,4-Diaminopyrimidines (pyrimethamine)
biguanides (proguanil# • chlorproguanil)
Sulfadoxine • sulfamethoxypyrazine
Coformulation
Fansidar# (sulfadoxine/pyrimethamine)
Other
Atovaquone (as Malarone)
Tetracycline • Doxycycline#
Clindamycin
Combi-
nations
Fixed-dose (coformulated) ACTs
artemether-lumefantrine#
artesunate-amodiaquine (ASAQ)
artesunate-mefloquine (ASMQ)
dihydroartemisinin-piperaquine
artesunate-pyronaridine
Other combinations
(not co-formulated)
artesunate/SP • artesunate/mefloquine •
quinine/tetracycline • quinine/doxycycline • quinine/clindamycin
Hetero-
kont

M: PRO

ambz, excv, chrm (strc)

ambz, excv, chrm

ambz, excv, chrm


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