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SML2386

Sigma-Aldrich

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:
152-53-4
Molecular Weight:
288.18
MDL number:
MFCD00035308
UNSPSC Code:
12352200

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

−20°C

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

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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
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)
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)
Cholwich Nattee et al.
Journal of molecular graphics & modelling, 71, 13-27 (2016-11-12)
Malaria is still one of the most serious diseases in tropical regions. This is due in part to the high resistance against available drugs for the inhibition of parasites, Plasmodium, the cause of the disease. New potent compounds with high
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