Cycloguanil
Cycloguanil (Chlorguanide triazine) is a dihydrofolate reductase (DHFR) inhibitor with an IC50 of 10.8 μM against human DHFR. Cycloguanil blocks the folate metabolic pathway, thereby affecting nucleotide synthesis and interfering with DNA replication. Cycloguanil inhibits DHFR in Plasmodium and is thus used in malaria research. Cycloguanil also potently inhibits DHFR in human cancer cells and blocks the transcriptional activity of STAT3, thereby exhibiting anticancer activity.
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- CAS No.: 516-21-2
- Formula: C11H14ClN5
- Molecular Weight:251.72
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Publications Citing Use of MedChemExpress (MCE) Cycloguanil
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Biological Activity
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Plasmodium |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| BC | IC50 |
>50 μM
Compound: Cycloguanil (C21)
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In vitro cytotoxicity against Plasmodium falciparum infected BC cell line.
In vitro cytotoxicity against Plasmodium falciparum infected BC cell line.
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[PMID: 14736247] |
| HeLa | EC50 |
>100 μM
Compound: 1
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Antiviral activity against coxsackie B4 virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against coxsackie B4 virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| HeLa | EC50 |
>100 μM
Compound: 1
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Antiviral activity against vesicular stomatitis virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against vesicular stomatitis virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| HeLa | EC50 |
0.55 μM
Compound: 1
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Antiviral activity against Respiratory syncytial virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against Respiratory syncytial virus infected in human HeLa cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| KB | IC50 |
41 μM
Compound: Cycloguanil (C21)
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In vitro cytotoxicity against Plasmodium falciparum infected KB cell line
In vitro cytotoxicity against Plasmodium falciparum infected KB cell line
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[PMID: 14736247] |
| MDCK | CC50 |
52 μM
Compound: 1
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Cytotoxicity against dog MDCK cells assessed as reduction in cell viability measured after 5 to 6 days by MTS assay
Cytotoxicity against dog MDCK cells assessed as reduction in cell viability measured after 5 to 6 days by MTS assay
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[PMID: 28477572] |
| Vero | EC50 |
>100 μM
Compound: 1
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Antiviral activity against Coxsackie B4 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against Coxsackie B4 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| Vero | EC50 |
>100 μM
Compound: 1
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Antiviral activity against para influenza 3 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against para influenza 3 virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| Vero | EC50 |
>100 μM
Compound: 1
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Antiviral activity against Punta Toro virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against Punta Toro virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| Vero | EC50 |
>100 μM
Compound: 1
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Antiviral activity against Reovirus 1 infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against Reovirus 1 infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| Vero | EC50 |
>100 μM
Compound: 1
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Antiviral activity against Sindbis virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against Sindbis virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| Vero | EC50 |
>100 μM
Compound: 1
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Antiviral activity against Yellow fever virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
Antiviral activity against Yellow fever virus infected in African green monkey Vero cells assessed as inhibition of viral-induced cytopathic effect measured after 3 to 6 days post infection by microscopic analysis
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[PMID: 28477572] |
| Vero | IC50 |
>50 μM
Compound: Cycloguanil (C21)
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In vitro cytotoxicity against Plasmodium falciparum infected vero cell line.
In vitro cytotoxicity against Plasmodium falciparum infected vero cell line.
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[PMID: 14736247] |
Cycloguanil exhibits anticancer activity against the NCI-60 panel of human tumor cell lines, and shows selective activity toward the MDA-MB-468 and MCF-7 breast cancer cell lines[2].
Cycloguanil (72 h) induces growth arrest in MDA-MB-468, MDA-MB-231 and MCF-7 breast cancer cells, with cell viability maintained at approximately 50% of that in the vehicle control group at high concentrations, and this effect cannot be reversed by folinic acid treatment[2].
Cycloguanil (0.001-10 μM; 24 h) binds to DHFR in intact MDA-MB-468 breast cancer cells, resulting in a dose-dependent accumulation of DHFR protein after 24 hours of treatment[2].
Cycloguanil (10 μM; 24 h) disrupts folate metabolism and nucleotide homeostasis in MDA-MB-231 breast cancer cells, and supplementation with Folinic acid (HY-17556) reverses the metabolite changes induced by it, a result consistent with DHFR inhibition[2].
Cycloguanil (0.02-20 μM; 6 h) potently inhibits the transcriptional activity of STAT3 in U3A fibrosarcoma cells at concentrations as low as 0.02 μM, which is consistent with the downstream effects of DHFR inhibition[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 516-21-2
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Molecular Weight 251.72
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Formula C11H14ClN5
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SMILES
NC1=NC(N)=NC(C)(C)N1C2=CC=C(Cl)C=C2
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Synonyms
Chlorguanide triazine
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Publications (3)
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Journal Impact Factor
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Most Recent
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Pharmaceuticals (Basel)
2024 Sep 19;17(9):1234. PMID: 39338396 -
Antimicrob Agents Chemother
Synergistic activity of RSL3 and Pyrimethamine to inhibit the proliferation of Plasmodium falciparum. [Abstract]2025 Aug 18:e0047125. PMID: 40823867 -
Purity & Documentation
References
[1]. Matthaei J, et al. OCT1 Deficiency Affects Hepatocellular Concentrations and Pharmacokinetics of Cycloguanil, the Active Metabolite of the Antimalarial Drug Proguanil. Clin Pharmacol Ther. 2019;105(1):190-200. [Content Brief]
[2]. Brown JI, et al. Cycloguanil and Analogues Potently Target DHFR in Cancer Cells to Elicit Anti-Cancer Activity. Metabolites. 2023;13(2):151. Published 2023 Jan 19. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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