| Identification | Back Directory | [Name]
Cycloguanil Hydrochloride | [CAS]
152-53-4 | [Synonyms]
BN 2410
NSC 3074
NSC 3074-d4
Cycloguanil Hydrochloride
Cycloguanil-d4 Hydrochloride
Chloroguanide Triazine Hydrochloride
Chloroguanide-d4 Triazine Hydrochloride
1-(4-Chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine Hydrochloride
1-(4-chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine hydrochloride
1-(4-Chlorophenyl-d4)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine Hydrochloride | [Molecular Formula]
C11H14ClN5.ClH | [MDL Number]
MFCD00035308 | [MOL File]
152-53-4.mol | [Molecular Weight]
288.181 |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
210-2150C | [storage temp. ]
-20?C Freezer | [solubility ]
DMSO (Slightly, Sonicated), Methanol (Slightly), Water (Slightly) | [form ]
Solid | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline Solid | [Uses]
Labelled antimalarial drug | [Description]
Cycloguanil is the active metabolite of the antimalarial prodrug proguanil. Cycloguanil is formed from proguanil by the cytochrome P450 (CYP) isoforms CYP2C19 and CYP3A in human liver microsomes. It is an inhibitor of dihydrofolate reductase (DHFR; Kis = 1.5 and 0.79 nM for the P. falciparum and P. berghei enzymes, respectively). It is active against ten P. falciparum field isolates (IC50s = 0.12-1,400 μg/ml). Cycloguanil reduces parasitemia in a mouse model of P. berghei infection (ED50 = 2 mg/kg). It also reduces parasitemia in a rhesus monkey model of P. cynomolgi infection when administered at a dose of 0.3 mg/kg. | [Definition]
ChEBI: Cycloguanil hydrochloride is the hydrochloride salt of cycloguanil. It is an organic molecular entity and a hydrochloride. It contains a cycloguanil. | [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. |
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