WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H530518
CAS#: 47326-86-3
Description: WR99210 is a dihydrofolate reductase inhibitor, which has promising in vitro activity against Mycobacterium avium complex (MAC). WR99210 has been shown to be effective against other mycobacteria. WR99210 is also a potent inhibitor of M. tuberculosis and Mycobacterium bovis BCG growth in vitro and that resistance to WR99210 occurred less frequently than resistance to either rifampin or isoniazid.
Hodoodo Cat#: H530518
Name: WR99210
CAS#: 47326-86-3
Chemical Formula: C14H18Cl3N5O2
Exact Mass: 393.05
Molecular Weight: 394.681
Elemental Analysis: C, 42.61; H, 4.60; Cl, 26.95; N, 17.74; O, 8.11
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Synonym: WR99210; WR 99210; WR-99210
IUPAC/Chemical Name: 1,6-Dihydro-6,6-dimethyl-1-[3-(2,4,5-trichlorophenoxy)propoxy]-1,3,5-triazine-2,4-diamine
InChi Key: MJZJYWCQPMNPRM-UHFFFAOYSA-N
InChi Code: 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)
SMILES Code: NC1=NC(N)=NC(C)(C)N1OCCCOC2=CC(Cl)=C(Cl)C=C2Cl
Appearance: White to off-white solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 394.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Asada M, Tanaka M, Goto Y, Yokoyama N, Inoue N, Kawazu S. Stable expression of green fluorescent protein and targeted disruption of thioredoxin peroxidase-1 gene in Babesia bovis with the WR99210/dhfr selection system. Mol Biochem Parasitol. 2012 Feb;181(2):162-70. doi: 10.1016/j.molbiopara.2011.11.001. PubMed PMID: 22108434.
2: Asada M, Yahata K, Hakimi H, Yokoyama N, Igarashi I, Kaneko O, Suarez CE, Kawazu S. Transfection of Babesia bovis by Double Selection with WR99210 and Blasticidin-S and Its Application for Functional Analysis of Thioredoxin Peroxidase-1. PLoS One. 2015 May 11;10(5):e0125993. doi: 10.1371/journal.pone.0125993. PubMed PMID: 25962142; PubMed Central PMCID: PMC4427477.
3: Gaffar FR, Wilschut K, Franssen FF, de Vries E. An amino acid substitution in the Babesia bovis dihydrofolate reductase-thymidylate synthase gene is correlated to cross-resistance against pyrimethamine and WR99210. Mol Biochem Parasitol. 2004 Feb;133(2):209-19. PubMed PMID: 14698433.
4: Japrung D, Leartsakulpanich U, Chusacultanachai S, Yuthavong Y. Conflicting requirements of Plasmodium falciparum dihydrofolate reductase mutations conferring resistance to pyrimethamine-WR99210 combination. Antimicrob Agents Chemother. 2007 Dec;51(12):4356-60. PubMed PMID: 17875995; PubMed Central PMCID: PMC2167985.
5: Gerum AB, Ulmer JE, Jacobus DP, Jensen NP, Sherman DR, Sibley CH. Novel Saccharomyces cerevisiae screen identifies WR99210 analogues that inhibit Mycobacterium tuberculosis dihydrofolate reductase. Antimicrob Agents Chemother. 2002 Nov;46(11):3362-9. PubMed PMID: 12384337; PubMed Central PMCID: PMC128743.
6: Hankins EG, Warhurst DC, Sibley CH. Novel alleles of the Plasmodium falciparum dhfr highly resistant to pyrimethamine and chlorcycloguanil, but not WR99210. Mol Biochem Parasitol. 2001 Sep 28;117(1):91-102. PubMed PMID: 11551635.
7: Hastings MD, Sibley CH. Pyrimethamine and WR99210 exert opposing selection on dihydrofolate reductase from Plasmodium vivax. Proc Natl Acad Sci U S A. 2002 Oct 1;99(20):13137-41. PubMed PMID: 12198181; PubMed Central PMCID: PMC130599.
8: Kinyanjui SM, Mberu EK, Winstanley PA, Jacobus DP, Watkins WM. The antimalarial triazine WR99210 and the prodrug PS-15: folate reversal of in vitro activity against Plasmodium falciparum and a non-antifolate mode of action of the prodrug. Am J Trop Med Hyg. 1999 Jun;60(6):943-7. PubMed PMID: 10403325.
9: Fidock DA, Wellems TE. Transformation with human dihydrofolate reductase renders malaria parasites insensitive to WR99210 but does not affect the intrinsic activity of proguanil. Proc Natl Acad Sci U S A. 1997 Sep 30;94(20):10931-6. PubMed PMID: 9380737; PubMed Central PMCID: PMC23535.
10: Ferlan JT, Mookherjee S, Okezie IN, Fulgence L, Sibley CH. Mutagenesis of dihydrofolate reductase from Plasmodium falciparum: analysis in Saccharomyces cerevisiae of triple mutant alleles resistant to pyrimethamine or WR99210. Mol Biochem Parasitol. 2001 Mar;113(1):139-50. PubMed PMID: 11254962.
11: Rieckmann KH, Yeo AE, Edstein MD. Activity of PS-15 and its metabolite, WR99210, against Plasmodium falciparum in an in vivo-in vitro model. Trans R Soc Trop Med Hyg. 1996 Sep-Oct;90(5):568-71. PubMed PMID: 8944276.
12: Edstein MD, Bahr S, Kotecka B, Shanks GD, Rieckmann KH. In vitro activities of the biguanide PS-15 and its metabolite, WR99210, against cycloguanil-resistant Plasmodium falciparum isolates from Thailand. Antimicrob Agents Chemother. 1997 Oct;41(10):2300-1. PubMed PMID: 9333069; PubMed Central PMCID: PMC164114.
13: Hekmat-Nejad M, Rathod PK. Plasmodium falciparum: kinetic interactions of WR99210 with pyrimethamine-sensitive and pyrimethamine-resistant dihydrofolate reductase. Exp Parasitol. 1997 Nov;87(3):222-8. PubMed PMID: 9371087.
14: Yeo AE, Seymour KK, Rieckmann KH, Christopherson RI. Effects of folic and folinic acids in the activities of cycloguanil and WR99210 against Plasmodium falciparum in erythrocytic culture. Ann Trop Med Parasitol. 1997 Jan;91(1):17-23. PubMed PMID: 9093425.
15: Rastelli G, Sirawaraporn W, Sompornpisut P, Vilaivan T, Kamchonwongpaisan S, Quarrell R, Lowe G, Thebtaranonth Y, Yuthavong Y. Interaction of pyrimethamine, cycloguanil, WR99210 and their analogues with Plasmodium falciparum dihydrofolate reductase: structural basis of antifolate resistance. Bioorg Med Chem. 2000 May;8(5):1117-28. PubMed PMID: 10882022.
16: Shah LM, DeStefano MS, Cynamon MH. Enhanced in vitro activity of WR99210 in combination with dapsone against Mycobacterium avium complex. Antimicrob Agents Chemother. 1996 Nov;40(11):2644-5. PubMed PMID: 8913480; PubMed Central PMCID: PMC163591.
17: Mui EJ, Jacobus D, Milhous WK, Schiehser G, Hsu H, Roberts CW, Kirisits MJ, McLeod R. Triazine Inhibits Toxoplasma gondii tachyzoites in vitro and in vivo. Antimicrob Agents Chemother. 2005 Aug;49(8):3463-7. PubMed PMID: 16048961; PubMed Central PMCID: PMC1196210.
18: Yeo AE, Christopherson RI. Comparative effects of cycloguanil and WR99210 in human leukaemia cells and intra-erythrocytic Plasmodium. Ann Trop Med Parasitol. 1998 Apr;92(3):331-3. PubMed PMID: 9713549.
19: Mokmak W, Chunsrivirot S, Hannongbua S, Yuthavong Y, Tongsima S, Kamchonwongpaisan S. Molecular dynamics of interactions between rigid and flexible antifolates and dihydrofolate reductase from pyrimethamine-sensitive and pyrimethamine-resistant Plasmodium falciparum. Chem Biol Drug Des. 2014 Oct;84(4):450-61. doi: 10.1111/cbdd.12334. PubMed PMID: 24716467.
20: Hunt SY, Detering C, Varani G, Jacobus DP, Schiehser GA, Shieh HM, Nevchas I, Terpinski J, Sibley CH. Identification of the optimal third generation antifolate against P. falciparum and P. vivax. Mol Biochem Parasitol. 2005 Dec;144(2):198-205. PubMed PMID: 16181688.
