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Triflurdine (Viroptic)

Anti-herpesvirus antiviral drug CAS# 70-00-8

Triflurdine (Viroptic)

Catalog No. BCC3873----Order now to get a substantial discount!

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Chemical structure

Triflurdine (Viroptic)

3D structure

Chemical Properties of Triflurdine (Viroptic)

Cas No. 70-00-8 SDF Download SDF
PubChem ID 253083 Appearance Powder
Formula C10H11F3N2O5 M.Wt 296.2
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Trifluridine; FTD; 5-Trifluorothymidine; NSC 529182; NSC 75520
Solubility DMSO : ≥ 100 mg/mL (337.61 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
SMILES C1C(C(OC1N2C=C(C(=O)NC2=O)C(F)(F)F)CO)O
Standard InChIKey VSQQQLOSPVPRAZ-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H11F3N2O5/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7/h2,5-7,16-17H,1,3H2,(H,14,18,19)
General tips For 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.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Triflurdine (Viroptic)

DescriptionNucleoside analog; inhibitor of thymidylate synthase. Incorporation of the triphosphate form into DNA induces DNA fragmentation. Exhibits antitumor activity.

Triflurdine (Viroptic) Dilution Calculator

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Triflurdine (Viroptic) Molarity Calculator

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Preparing Stock Solutions of Triflurdine (Viroptic)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3761 mL 16.8805 mL 33.761 mL 67.5219 mL 84.4024 mL
5 mM 0.6752 mL 3.3761 mL 6.7522 mL 13.5044 mL 16.8805 mL
10 mM 0.3376 mL 1.688 mL 3.3761 mL 6.7522 mL 8.4402 mL
50 mM 0.0675 mL 0.3376 mL 0.6752 mL 1.3504 mL 1.688 mL
100 mM 0.0338 mL 0.1688 mL 0.3376 mL 0.6752 mL 0.844 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Triflurdine (Viroptic)

Trifluridine (also called trifluorothymidine or TFT) is an anti-herpesvirus antiviral drug, used primarily on the eye. It was sold under the trade name, Viroptic, by Glaxo Wellcome, now merged into GlaxoSmithKline. The brand is now owned by Monarch Pharmaceuticals, which is wholly owned by King Pharmaceuticals.

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References on Triflurdine (Viroptic)

Small molecules enhance CRISPR genome editing in pluripotent stem cells.[Pubmed:25658371]

Cell Stem Cell. 2015 Feb 5;16(2):142-7.

The bacterial CRISPR-Cas9 system has emerged as an effective tool for sequence-specific gene knockout through non-homologous end joining (NHEJ), but it remains inefficient for precise editing of genome sequences. Here we develop a reporter-based screening approach for high-throughput identification of chemical compounds that can modulate precise genome editing through homology-directed repair (HDR). Using our screening method, we have identified small molecules that can enhance CRISPR-mediated HDR efficiency, 3-fold for large fragment insertions and 9-fold for point mutations. Interestingly, we have also observed that a small molecule that inhibits HDR can enhance frame shift insertion and deletion (indel) mutations mediated by NHEJ. The identified small molecules function robustly in diverse cell types with minimal toxicity. The use of small molecules provides a simple and effective strategy to enhance precise genome engineering applications and facilitates the study of DNA repair mechanisms in mammalian cells.

Involvement of concentrative nucleoside transporter 1 in intestinal absorption of trifluorothymidine, a novel antitumor nucleoside, in rats.[Pubmed:22076553]

J Pharmacol Exp Ther. 2012 Feb;340(2):457-62.

alphaalphaalpha-Trifluorothymidine (TFT), an anticancer nucleoside analog, is a potent thymidylate synthase inhibitor. TFT exerts its antitumor activity primarily by inducing DNA fragmentation after incorporation of the triphosphate form of TFT into the DNA. Although an oral combination of TFT and a thymidine phosphorylase inhibitor has been clinically developed, there is little information regarding TFT absorption. Therefore, we investigated TFT absorption in the rat small intestine. After oral administration of TFT in rats, more than 75% of the TFT was absorbed. To identify the uptake transport system, uptake studies were conducted by using everted sacs prepared from rat small intestines. TFT uptake was saturable, significantly reduced under Na(+)-free conditions, and strongly inhibited by the addition of an endogenous pyrimidine nucleoside. From these results, we suggested the involvement of concentrative nucleoside transporters (CNTs) in TFT absorption into rat small intestine. In rat small intestines, the mRNAs coding for rat CNT1 (rCNT1) and rCNT2, but not for rCNT3, were predominantly expressed. To investigate the roles of rCNT1 and rCNT2 in TFT uptake, we conducted uptake assays by using Xenopus laevis oocytes injected with rCNT1 complementary RNA (cRNA) and rCNT2 cRNA. TFT uptake by X. laevis oocytes injected with rCNT1 cRNA, and not rCNT2 cRNA, was significantly greater than that by water-injected oocytes. In addition, in situ single-pass perfusion experiments performed using rat jejunum regions showed that thymidine, a substrate for CNT1, strongly inhibited TFT uptake. In conclusion, TFT is absorbed via rCNT1 in the intestinal lumen in rats.

Potentiation of the antitumor activity of alpha, alpha, alpha-trifluorothymidine by the co-administration of an inhibitor of thymidine phosphorylase at a suitable molar ratio in vivo.[Pubmed:16010427]

Int J Oncol. 2005 Aug;27(2):449-55.

Trifluorothymidine (FTD) is a thymidine analog that exhibits an antitumor activity through its inhibition of thymidylate synthase and its incorporation into DNA. However, FTD is rapidly hydrolyzed to an inactive form by thymidine phosphorylase (TP). We attempted to augment the antitumor activity of FTD by combining it with a potent and reversible inhibitor of TP, 5-chloro-6-(2-imino-propyrrolidin-1-yl) methyl-2, 4 (1H, 3H)-pyrimidinedione hydrochloride (TPI) in human tumor xenografts with a low sensitivity to 5-fluorouracil. The optimum ratio of TPI to FTD was determined by measuring the maximum plasma level of FTD after oral administration and the antitumor effect of FTD on human tumor xenografts in mice. When > 0.5 M of TPI and 1 M of FTD (10 mg/kg) were co-administered, the plasma FTD levels in mice and monkeys were elevated, almost reaching a maximal and constant value of 20-30 microg/ml and 15 microg/ml, respectively. When human gastrointestinal cancer cell lines (DLD-1, CO-3 and AZ521) were xenografted into nude mice, the antitumor activity of FTD was augmented by the co-administration of TPI, compared to that of FTD alone, and the ED50 value, used to indicate the antitumor effect, reached a maximum value (about 25, 20, and 10 mg/kg in the DLD-1, CO-3, and AZ521 tumors, respectively) when > 0.5 M of TPI was combined with 1 M of FTD. The oral administration of TPI markedly improved the FTD-induced toxicity, as evaluated by the decrease in the body weight of the mice. These results suggested that the optimum ratio of FTD to TPI was 1:0.5 M, enabling a high antitumor activity and a low toxicity. We further evaluated whether TPI inhibits TP-induced angiogenesis in a gelatin-sponge mouse model, based on the finding that TP is identical to platelet-derived endothelial cell growth factor. Ten and 30 mg/kg administration of TPI significantly inhibited TP-induced neovascularization in a dose-dependent manner in a mouse model. The above results suggest that the combination of TPI and an antitumor nucleoside, FTD, not only enhances the antitumor efficacy and decreases the toxicity of FTD, but also suppresses TP-induced angiogenesis.

Description

Trifluridine (Trifluorothymidine; 5-Trifluorothymidine; TFT) is an irreversible thymidylate synthase inhibitor, and thereby suppresses DNA synthesis. Trifluridine is an antiviral drug for herpes simplex virus (HSV) infection.

Keywords:

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