| Identification | Back Directory | [Name]
BRL 6231 | [CAS]
47326-86-3 | [Synonyms]
BRL 6231
WR-99210
1,6-Dihydro-6,6-dimethyl-1-[3-(2,4,5-trichlorophenoxy)propoxy]-1,3,5-triazine-2,4-diamine
6,6-dimethyl-1-(3-(2,4,5-trichlorophenoxy)propoxy)-1,6-dihydro-1,3,5-triazine-2,4-diamine
5-[3-(2,4,5-Trichlorophenoxy)propoxy]-6,6-dimethyl-5,6-dihydro-1,3,5-triazine-2,4-diamine
1-[3-[(2,4,5-Trichlorophenyl)oxy]propoxy]-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine | [Molecular Formula]
C14H18Cl3N5O2 | [MDL Number]
MFCD01679034 | [MOL File]
47326-86-3.mol | [Molecular Weight]
394.68 |
| Chemical Properties | Back Directory | [Boiling point ]
519.7±60.0 °C(Predicted) | [density ]
1.52±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble0.2mg/mL, clear (warmed) | [form ]
powder | [pka]
8.48±0.40(Predicted) | [color ]
white to off-white | [InChI]
1S/C14H18Cl3N5O2/c1-14(2)21-12(18)20-13(19)22(14)24-5-3-4-23-11-7-9(16)8(15)6-10(11)17/h6-7H,3-5H2,1-2H3,(H4,18,19,20,21) | [InChIKey]
MJZJYWCQPMNPRM-UHFFFAOYSA-N | [SMILES]
CC1(C)N=C(N)N=C(N)N1OCCCOc2cc(Cl)c(Cl)cc2Cl |
| Hazard Information | Back Directory | [Uses]
WR99210 is an orally active and low-toxicity dihydrofolate reductase (DHFR) inhibitor (IC50<0.075 nM). WR99210 shows good antiparasitic activity and is effective against P. falciparum and P. falciparum strains (including Pyrimethamine.html" class="link-product" target="_blank">Pyrimethamine (HY-18062)-resistant P. falciparum strains) as well as T. gondii[1][2][3]. | [Biochem/physiol Actions]
WR99210 is a potent inhibitor of Plasmodium falciparum dihydrofolate reductase (DHFR), which is a major malarial drug target. It has subnanomolar potency for the wild type, double mutant and quadruple mutant dihydrofolate reductases. | [in vivo]
WR99210 (1.25 mg/kg; i.p.; single daily for 5 days) is highly effective against T. gondii tachyzoites in a mouse model[1]. | Animal Model: | Male mice (T. gondii-infected)[1]. | | Dosage: | 1.25 mg/kg | | Administration: | Intraperitoneal injection; single daily for 5 days. | | Result: | Exhibited intraperitoneal parasite numbers were 2 logs less in mice on the day 5. |
| [References]
[1] Mui EJ, et al. Triazine Inhibits Toxoplasma gondii tachyzoites in vitro and in vivo. Antimicrob Agents Chemother. 2005 Aug;49(8):3463-7. DOI:10.1128/AAC.49.8.3463-3467.2005
[2] Hastings MD, et al. Pyrimethamine and WR99210 exert opposing selection on dihydrofolatereductase from Plasmodium vivax. Proc Natl Acad Sci U S A. 2002 Oct 1;99(20):13137-41. DOI:10.1073/pnas.182295999
[3] Kiara SM, et al. In vitro activity of antifolate and polymorphism in dihydrofolate reductase of Plasmodium falciparum isolates from the Kenyan coast: emergence of parasites with Ile-164-Leu mutation. Antimicrob Agents Chemother. 2009 Sep;53(9):3793-8. DOI:10.1128/AAC.00308-09 |
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