Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H14ClN5 |
| Molecular Weight | 251.715 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)N=C(N)N=C(N)N1C2=CC=C(Cl)C=C2
InChI
InChIKey=QMNFFXRFOJIOKZ-UHFFFAOYSA-N
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)
| Molecular Formula | C11H14ClN5 |
| Molecular Weight | 251.715 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Cycloguanil is a dihydrofolate reductase inhibitor and is a metabolite of the antimalarial drug proguanil. The parent drug proguanil was suggested to contribute to the antimalarial activity as well, but the mechanism of action is unknown. Proguanil is a prodrug that is metabolized to its main active metabolite, cycloguanil, mostly via CYP2C19. There is significant variation in proguanil pharmacokinetics.12 CYP2C19 is the predominant enzyme catalyzing the bioactivation of proguanil to cycloguanil. Cycloguanil is one of the few antimalarial drugs that act on both the erythrocytic and on the pre-erythrocytic (hepatic) forms of the malaria parasites. 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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Catalytic and ligand-binding characteristics of Plasmodium falciparum serine hydroxymethyltransferase. | 2009-11 |
|
| Structure-activity relationship and comparative docking studies for cycloguanil analogs as PfDHFR-TS inhibitors. | 2009-07 |
|
| A systematic review and meta-analysis of evidence for correlation between molecular markers of parasite resistance and treatment outcome in falciparum malaria. | 2009-05-04 |
|
| WISDOM-II: screening against multiple targets implicated in malaria using computational grid infrastructures. | 2009-05-01 |
|
| Multiple origins and regional dispersal of resistant dhps in African Plasmodium falciparum malaria. | 2009-04-14 |
|
| Analysis of genetic mutations associated with anti-malarial drug resistance in Plasmodium falciparum from the Democratic Republic of East Timor. | 2009-04-09 |
|
| A novel in silico approach to drug discovery via computational intelligence. | 2009-04 |
|
| Interactions between cycloguanil derivatives and wild type and resistance-associated mutant Plasmodium falciparum dihydrofolate reductases. | 2009-04 |
|
| Indigenous evolution of Plasmodium falciparum pyrimethamine resistance multiple times in Africa. | 2009-02 |
|
| Molecular characterization of antifolates resistance-associated genes, (dhfr and dhps) in Plasmodium vivax isolates from the Middle East. | 2009-01-28 |
|
| Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents. | 2008-12-15 |
|
| Mutations in the Plasmodium falciparum cytochrome b gene are associated with delayed parasite recrudescence in malaria patients treated with atovaquone-proguanil. | 2008-11-20 |
|
| Prevalence of pfmdr1, pfcrt, pfdhfr and pfdhps mutations associated with drug resistance, in Luanda, Angola. | 2008-11-17 |
|
| Molecular epidemiology of drug-resistant malaria in western Kenya highlands. | 2008-07-31 |
|
| Escalating Plasmodium falciparum antifolate drug resistance mutations in Macha, rural Zambia. | 2008-05-21 |
|
| Effect of folate derivatives on the activity of antifolate drugs used against malaria and cancer. | 2008-05 |
|
| The usefulness of twenty-four molecular markers in predicting treatment outcome with combination therapy of amodiaquine plus sulphadoxine-pyrimethamine against falciparum malaria in Papua New Guinea. | 2008-04-19 |
|
| Novel triazine JPC-2067-B inhibits Toxoplasma gondii in vitro and in vivo. | 2008-03-05 |
|
| Sulphadoxine/pyrimethamine versus amodiaquine for treating uncomplicated childhood malaria in Gabon: a randomized trial to guide national policy. | 2008-02-12 |
|
| Plasmodium falciparum malaria and atovaquone-proguanil treatment failure. | 2008-02 |
|
| Role of specific cytochrome P450 isoforms in the conversion of phenoxypropoxybiguanide analogs in human liver microsomes to potent antimalarial dihydrotriazines. | 2008-02 |
|
| Modelling and informatics in the analysis of P. falciparum DHFR enzyme inhibitors. | 2008 |
|
| Prevalence of mutations associated with antimalarial drugs in Plasmodium falciparum isolates prior to the introduction of sulphadoxine-pyrimethamine as first-line treatment in Iran. | 2007-11-13 |
|
| Antimalarial drug susceptibility and point mutations associated with drug resistance in 248 Plasmodium falciparum isolates imported from Comoros to Marseille, France in 2004 2006. | 2007-09 |
|
| A novel Plasmodium falciparum expression system for assessing antifolate resistance caused by mutant P. vivax dihydrofolate reductase-thymidylate synthase. | 2007-08-01 |
|
| The role of tryptophan-48 in catalysis and binding of inhibitors of Plasmodium falciparum dihydrofolate reductase. | 2007-06 |
|
| Effect of honey on CYP3A4, CYP2D6 and CYP2C19 enzyme activity in healthy human volunteers. | 2007-04 |
|
| Analysis of sulphadoxine/pyrimethamine resistance-conferring mutations of Plasmodium falciparum from Mozambique reveals the absence of the dihydrofolate reductase 164L mutant. | 2007-03-23 |
|
| Simultaneous determination of monodesethylchloroquine, chloroquine, cycloguanil and proguanil on dried blood spots by reverse-phase liquid chromatography. | 2007-02-19 |
|
| Intermittent preventive treatment for malaria in pregnancy in Africa: what's new, what's needed? | 2007-02-16 |
|
| Molecular surveillance of drug-resistance associated mutations of Plasmodium falciparum in south-west Tanzania. | 2007-01-15 |
|
| Rapid dissemination of Plasmodium falciparum drug resistance despite strictly controlled antimalarial use. | 2007-01-03 |
|
| Integration and mining of malaria molecular, functional and pharmacological data: how far are we from a chemogenomic knowledge space? | 2006-11-17 |
|
| Drug resistance to sulphadoxine-pyrimethamine in Plasmodium falciparum malaria in Mlimba, Tanzania. | 2006-10-31 |
|
| Amino acid mutations in Plasmodium vivax DHFR and DHPS from several geographical regions and susceptibility to antifolate drugs. | 2006-10 |
|
| Urban malaria in Dakar, Senegal: chemosusceptibility and genetic diversity of Plasmodium falciparum isolates. | 2006-07 |
|
| In vitro activity of iron-binding compounds against Senegalese isolates of Plasmodium falciparum. | 2006-06 |
|
| Population pharmacokinetic and pharmacodynamic modelling of the antimalarial chemotherapy chlorproguanil/dapsone. | 2006-03 |
|
| Multiple synergistic interactions between atovaquone and antifolates against Plasmodium falciparum in vitro: a rational basis for combination therapy. | 2006-03 |
|
| Sensitive method for the quantitative determination of proguanil and its metabolites in rat blood and plasma by liquid chromatography-mass spectrometry. | 2006-01-18 |
|
| Plasmodium falciparum: interaction of shikimate analogues with antimalarial drugs. | 2005-11 |
|
| [Chemosusceptibility analysis of Plasmodium falciparum imported from Comoros to Marseilles, France in 2001-2003]. | 2005-10 |
|
| Susceptibility studies of Malaysian Plasmodium falciparum clones to type II antifolate drugs after 3 years of continuous in vitro culture. | 2005-10 |
|
| A simple dual selection for functionally active mutants of Plasmodium falciparum dihydrofolate reductase with improved solubility. | 2005-10 |
|
| The pharmacokinetics and pharmacodynamics of atovaquone and proguanil for the treatment of uncomplicated falciparum malaria in third-trimester pregnant women. | 2005-09 |
|
| The chemotherapy of rodent malaria. LXIII. Drug combinations to impede the selection of drug resistance, part 6: the potential value of chlorproguanil and dapsone in combination, and with the addition of artesunate. | 2005-07 |
|
| Shikimate and folate pathways in the protozoan parasite, Perkinsus olseni. | 2005-07 |
|
| In vitro metabolism of phenoxypropoxybiguanide analogues in human liver microsomes to potent antimalarial dihydrotriazines. | 2005-04-21 |
|
| Malarial (Plasmodium falciparum) dihydrofolate reductase-thymidylate synthase: structural basis for antifolate resistance and development of effective inhibitors. | 2005-03 |
|
| Malaria epidemic and drug resistance, Djibouti. | 2005-02 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:53:18 GMT 2025
by
admin
on
Mon Mar 31 17:53:18 GMT 2025
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| Record UNII |
26RM326WVN
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-ATC |
P01BB02
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NCI_THESAURUS |
C2153
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26RM326WVN
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100000084674
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C026009
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754
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DB14763
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m3984
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SUB01526MIG
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Cycloguanil
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516-21-2
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C81015
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET ORGANISM->INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
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