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 |
|---|---|---|
| Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. | 2001 Jan |
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| Analysis of proguanil and its metabolites by application of the sweeping technique in micellar electrokinetic chromatography. | 2001 May 4 |
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| Resistance to antifolates in Plasmodium falciparum, the causative agent of tropical malaria. | 2002 |
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| Time-dependent pharmacokinetics and drug metabolism of atovaquone plus proguanil (Malarone) when taken as chemoprophylaxis. | 2002 Apr |
|
| Mutational analysis of Plasmodium falciparum dihydrofolate reductase: the role of aspartate 54 and phenylalanine 223 on catalytic activity and antifolate binding. | 2002 May |
|
| Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. | 2002 Nov |
|
| Monitoring the drug-sensitivity of Plasmodium falciparum in coastal towns in Madagascar by use of in vitro chemosensitivity and mutation detection tests. | 2002 Sep |
|
| Malaria: use of restriction endonuclease digestion and mutation-specific PCR for antifolate resistance isolate detection. | 2003 Mar |
|
| Pharmacodynamic interactions among atovaquone, proguanil and cycloguanil against Plasmodium falciparum in vitro. | 2003 May-Jun |
|
| 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 Jul |
|
| Plasmodium falciparum: interaction of shikimate analogues with antimalarial drugs. | 2005 Nov |
|
| A novel Plasmodium falciparum expression system for assessing antifolate resistance caused by mutant P. vivax dihydrofolate reductase-thymidylate synthase. | 2007 Aug 1 |
|
| 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 Sep |
|
| 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 Apr 19 |
|
| Novel triazine JPC-2067-B inhibits Toxoplasma gondii in vitro and in vivo. | 2008 Mar 5 |
|
| Escalating Plasmodium falciparum antifolate drug resistance mutations in Macha, rural Zambia. | 2008 May 21 |
|
| Multiple origins and regional dispersal of resistant dhps in African Plasmodium falciparum malaria. | 2009 Apr 14 |
|
| Indigenous evolution of Plasmodium falciparum pyrimethamine resistance multiple times in Africa. | 2009 Feb |
|
| Structure-activity relationship and comparative docking studies for cycloguanil analogs as PfDHFR-TS inhibitors. | 2009 Jul |
|
| WISDOM-II: screening against multiple targets implicated in malaria using computational grid infrastructures. | 2009 May 1 |
|
| A systematic review and meta-analysis of evidence for correlation between molecular markers of parasite resistance and treatment outcome in falciparum malaria. | 2009 May 4 |
|
| Catalytic and ligand-binding characteristics of Plasmodium falciparum serine hydroxymethyltransferase. | 2009 Nov |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:18:00 GMT 2023
by
admin
on
Fri Dec 15 15:18:00 GMT 2023
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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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DTXSID9022867
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DB14763
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m3984
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SUB01526MIG
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Cycloguanil
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9049
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516-21-2
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C81015
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| Related Record | Type | Details | ||
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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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| Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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|---|---|---|---|---|
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ACTIVE MOIETY |
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