SML2386
Cycloguanil hydrochloride
≥95% (HPLC)
Synonym(s):
1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C11H14ClN5 · HCl
CAS Number:
Molecular Weight:
288.18
UNSPSC Code:
12352200
MDL number:
NACRES:
NA.21
SMILES string
Clc1ccc(cc1)N2C(NC(=N)NC2=N)(C)C.Cl
InChI
1S/C11H14ClN5.ClH/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);1H
InChI key
MOUAPRKJJUXEIE-UHFFFAOYSA-N
assay
≥95% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
H2O: 2 mg/mL, clear
storage temp.
−20°C
Related Categories
Application
Cycloguanil hydrochloride is suitable for use as a positive control in screening Plasmodium falciparum strains in microdilution radioisotope antiplasmodial bioassay. It may also be used as internal standard in high performance liquid chromatography for the quantification of urine and plasma samples.
Biochem/physiol Actions
Cycloguanil is it a potential antimalarial drug. It is hydrophilic in nature. Cycloguanil acts as a substrate for the enzyme organic cation transporter 1 (OCT1).
Cycloguanil, a metabolite of proguanil, is a potent dihydrofolate reductase inhibitor.
Dihydrofolate reductase inhibitor, metabolite of proguanil
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
4.1B - Flammable solid hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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GC/GC-MS analysis, isolation and identification of bioactive essential oil components from the Bhutanese medicinal plant, Pleurospermum amabile
Wangchuk P, et al.
Natural Product Communications, 8(9), 1934578X1300800930-1934578X1300800930 (2013)
OCT 1 Deficiency Affects Hepatocellular Concentrations and Pharmacokinetics of Cycloguanil, the Active Metabolite of the Antimalarial Drug Proguanil
Matthaei J, et al.
Clinical Pharmacology and Therapeutics, 105(1), 190-200 (2019)
Sensitive high performance liquid chromatographic method for the determination of proguanil and its metabolites, cycloguanil and 4-chlorophenylbiguanide in biological fluids
Ebeshi BU, et al.
African Journal of Biotechnology, 4(8), 856-861 (2005)
Michele Tonelli et al.
European journal of medicinal chemistry, 135, 467-478 (2017-05-10)
We have identified a series of 1-aryl-4,6-diamino-1,2-dihydrotriazines, structurally related to the antimalarial drug cycloguanil, as new inhibitors of influenza A and B virus and respiratory syncytial virus (RSV) via targeting of the host dihydrofolate reductase (DHFR) enzyme. Most analogues proved
Phenylpropanoids and furanocoumarins as antibacterial and antimalarial constituents of the Bhutanese medicinal plant Pleurospermum amabile
Wangchuk P, et al.
Natural Product Communications, 9(7), 1934578X1400900719-1934578X1400900719 (2014)
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