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Sigma-Aldrich |
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021-61415566 800-8193336 |
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orderCN@merckgroup.com |
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| | BRL 6231 Basic information |
| Product Name: | BRL 6231 | | Synonyms: | BRL 6231;1-[3-[(2,4,5-Trichlorophenyl)oxy]propoxy]-1,6-dihydro-6,6-dimethyl-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;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;Antifolate,Inhibitor,Bacterial,WR 99210,inhibit,WR99210,WR-99210;1,3,5-Triazine-2,4-diamine, 1,6-dihydro-6,6-dimethyl-1-[3-(2,4,5-trichlorophenoxy)propoxy]- | | CAS: | 47326-86-3 | | MF: | C14H18Cl3N5O2 | | MW: | 394.68 | | EINECS: | | | Product Categories: | | | Mol File: | 47326-86-3.mol |  |
| | BRL 6231 Chemical Properties |
| 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) | | pka | 8.48±0.40(Predicted) | | form | powder | | 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 |
| WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | BRL 6231 Usage And Synthesis |
| 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 (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 |
| | BRL 6231 Preparation Products And Raw materials |
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