Structure via PubChem · Public domain (PubChem)
cycloguanil
Sign in to saveAlso known as 1-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamine
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.
Chemical data
- Formula
- C11H14ClN5
- Molecular weight
- 251.71 g/mol
- IUPAC name
- 1-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamine
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
404 papers- Cycloguanil and Analogues Potently Target DHFR in Cancer Cells to Elicit Anti-Cancer Activity.Metabolites · 2023
- Structural Insights into the Development of Cycloguanil Derivatives as Trypanosoma brucei Pteridine-Reductase-1 Inhibitors.ACS infectious diseases · 2019
- OCT1 Deficiency Affects Hepatocellular Concentrations and Pharmacokinetics of Cycloguanil, the Active Metabolite of the Antimalarial Drug Proguanil.Clinical pharmacology and therapeutics · 2019
- Evidence of Pyrimethamine and Cycloguanil Analogues as Dual Inhibitors of Trypanosoma brucei Pteridine Reductase and Dihydrofolate Reductase.Pharmaceuticals (Basel, Switzerland) · 2021
- Identification of Innovative Folate Inhibitors Leveraging the Amino Dihydrotriazine Motif from Cycloguanil for Their Potential as Anti-Trypanosoma brucei Agents.ACS infectious diseases · 2024
via PubMed
Wikidata facts
- Mass
- 251.094
Show 3 more facts
- chemical formula
- C₁₁H₁₄ClN₅
- canonical SMILES
- CC1(N=C(N=C(N1C2=CC=C(C=C2)Cl)N)N)C
- Commons category
- Cycloguanil
Sources (2)
via Wikidata · CC0
~1 min read
Article
2 sectionsContents
- Synthesis
- References
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.