Cycloguanil

Cycloguanil

File:Cycloguanil.svg
File:Cycloguanil sf.png
Systematic (IUPAC) name
1-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamine
Identifiers
CAS Number	516-21-2 Y
ATC code	P01BB02 (WHO)
PubChem	CID: 9049
ChemSpider	8697 Y
UNII	26RM326WVN Y
ChEMBL	CHEMBL747 Y
Chemical data
Formula	C11H14ClN5
Molecular mass	251.715 g/mol
SMILES Clc1ccc(cc1)N2C(=N/C(=N\C2(C)C)N)\N
InChI InChI=1S/C11H14ClN5/c1-11(2)16-9(13)15-10(14)17(11)8-5-3-7(12)4-6-8/h3-6H,1-2H3,(H4,13,14,15,16) Y Key:QMNFFXRFOJIOKZ-UHFFFAOYSA-N Y
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Cycloguanil is a dihydrofolate reductase inhibitor, and is a metabolite of the antimalarial drug proguanil; its formation in vivo has been thought to be primarily responsible for the antimalarial activity of proguanil. However, more recent work has indicated that, while proguanil is synergistic with the drug atovaquone (as in the combination Malarone), cycloguanil is in fact antagonistic to the effects of atovaquone, suggesting that, unlike cycloguanil, proguanil may have an alternative mechanism of antimalarial action besides dihydrofolate reductase inhibition.

Although cycloguanil is not currently in general use as an antimalarial, the continuing development of resistance to current antimalarial drugs has led to renewed interest in studying the use of cycloguanil in combination with other drugs.