A prodrug form of cycloguanil
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Proguanil

Item No. 30675

Technical Information
Formal Name
N-(4-chlorophenyl)-N′-(1-methylethyl)-imidodicarbonimidic diamide
CAS Number
500-92-5
Synonyms
  • Chlorguanide
  • Chloroguanide
Molecular Formula
C11H16ClN5
Formula Weight
Purity
≥98%
A solid
DMF: 1 mg/mlDMSO: 1 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.05 mg/mlEthanol: 1 mg/ml
λmax
259 nm
SMILES
ClC1=CC=C(NC(NC(NC(C)C)=N)=N)C=C1
InChi Code
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)
InChi Key
SSOLNOMRVKKSON-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Proguanil is a prodrug form of the antimalarial agent cycloguanil (Item No. 16861).1 Proguanil is metabolized by the cytochrome P450 (CYP) isoforms CYP2C19 and CYP3A to form cycloguanil in human liver microsomes. It is active against chloroquine- and quinine-resistant strains of P. falciparum alone or in combination with atovaquone (Item No. 23802) with EC50 values ranging from 0.22 to 2.67 and 0.37 to 1.6 µM, respectively.2 It reduces parasitemia in a mouse model of P. berghei infection with a minimum effective dose (MED) of 32 mg/kg.3 Formulations containing proguanil have been used in combination with atovaquone for the prevention and treatment of malaria.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Birkett, D.J., Rees, D., Anderson, T., et alIn vitro proguanil activation to cycloguanil by human liver microsomes is mediated by CYP3A isoforms as well as by S-mephenytoin hydroxylase. Br. J. Clin. Pharmacol. 37(5), 413-420 (1994).

    2. Thapar, M.M., Gupta, S., Spindler, C., et alPharmacodynamic interactions among atovaquone, proguanil and cycloguanil against Plasmodium falciparum in vitro. Trans. R. Soc. Trop. Med. Hyg. 97(3), 331-337 (2003).

    3. Black, R.H., and Ray, A.P. Experimental studies of the potentiation of proguanil and pyrimethamine by dapsone using Plasmodium berghei in white mice. Ann. Trop. Med. Parasitol. 71(2), 131-139 (1977).