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Cycloguanil (hydrochloride)

Catalog No.
C5763
inhibitor of dihydrofolate reductase (DHFR)
Grouped product items
SizePriceStock Qty
10mg
$57.00
Ship with 5-10 days
25mg
$107.00
Ship with 5-10 days
50mg
$150.00
Ship with 5-10 days

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Background

Cycloguanil is an inhibitor of dihydrofolate reductase (DHFR)[1].

Dihydrofolate reductase (DHFR) is an enzyme that involved in reducing dihydrofolic acid to tetrahydrofolic acid. DHFR plays a critical role in regulating the amount of tetrahydrofolate in the cell, which are essential for purine and thymidylate synthesis important for cell proliferation and cell growth. DHFR also plays a central role in the synthesis of nucleic acid precursors and salvage of tetrahydrobiopterin from dihydrobiopterin [2].

Cycloguanil is the active metabolite of proguanil produced by the cytochrome P450 (CYP) [3]. Cycloguanil showed activity against P. falciparu. Cycloguanil inhibited the activity of dihydrofolate reductase (DHFR) with the Ki values of 0.3 and 1.5 nM for Plasmodium and human forms, respectively., Cycloguanil prevented the production of tetrahydrofolic acid, an essential coenzyme involved in DNA and RNA synthesis, by blocking DHFR activity.

References:
[1] Foote S J, Galatis D, Cowman A F.  Amino acids in the dihydrofolate reductase-thymidylate synthase gene of Plasmodium falciparum involved in cycloguanil resistance differ from those involved in pyrimethamine resistance[J]. Proceedings of the National Academy of Sciences, 1990, 87(8): 3014-3017.
[2] Blakley R L.  Dihydrofolate reductase[J]. Encyclopedia Of Molecular Medicine, 1984.
[3] Birkett D J, Rees D, Andersson T, et al.  In vitro proguanil activation to cycloguanil by human liver microsomes is mediated by CYP3A isoforms as well as by S‐mephenytoin hydroxylase[J]. British journal of clinical pharmacology, 1994, 37(5): 413-420.

Chemical Properties

Physical AppearanceA crystalline solid
StorageStore at -20°C
M.Wt288.2
Cas No.152-53-4
FormulaC11H14ClN5·HCl
SynonymsChloroguanide Triazine,NSC 3074
Solubility≤5mg/ml in ethanol;20mg/ml in DMSO;5mg/ml in dimethyl formamide
Chemical Name1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine, monohydrochloride
SDFDownload SDF
Canonical SMILESClC1=CC=C(N2C(N)=NC(N)=NC2(C)C)C=C1.Cl
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Quality Control

Quality Control & MSDS

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Chemical structure

Cycloguanil (hydrochloride)