RX-3117
new
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 206092

CAS#: 865838-26-2

Description: RX-3117, also known as TV-1360 and fluorocyclopentenylcytosine, is an orally available and potent DNA synthesis inhibitor with potential antineoplastic activity. Upon administration, the cytidine analogue RX-3117 is taken up by cells through a carrier-mediated transporter, phosphorylated by uridine cytidine kinase (UCK) and then further phosphorylated to its diphosphate (RX-DP) and triphosphate forms (RX-TP). The triphosphate form is incorporated into RNA and inhibits RNA synthesis. The diphosphate RX-DP is reduced by ribonucleotide reductase (RR) to dRX-DP; its triphosphate form (dRX-TP) is incorporated into DNA. In addition, RX-3117 also inhibits DNA methyltransferase 1 (DNMT1).

Chemical Structure

img
RX-3117
CAS# 865838-26-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 206092
Name: RX-3117
CAS#: 865838-26-2
Chemical Formula: C10H12FN3O4
Exact Mass: 257.08
Molecular Weight: 257.220
Elemental Analysis: C, 46.69; H, 4.70; F, 7.39; N, 16.34; O, 24.88

Price and Availability

Size Price Availability Quantity
50mg USD 950 2 Weeks
100mg USD 1750 2 Weeks
200mg USD 2450 2 Weeks
500mg USD 3650 2 Weeks
1g USD 4850 2 Weeks
2g USD 7850 2 Weeks
Bulk inquiry

Synonym: RX3117; RX3117; RX 3117; TV1360; TV1360; TV 1360; fluorocyclopentenylcytosine

IUPAC/Chemical Name: 4-(4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-(pyridin-4-yl)-1H-imidazol-2-yl)but-3-yn-1-ol

InChi Key: QSUSKMBNZQHHPA-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H24FN3O/c28-24-13-11-22(12-14-24)26-27(23-15-17-29-18-16-23)31(25(30-26)10-4-5-20-32)19-6-9-21-7-2-1-3-8-21/h1-3,7-8,11-18,32H,5-6,9,19-20H2

SMILES Code: OCCC#CC1=NC(C2=CC=C(F)C=C2)=C(C3=CC=NC=C3)N1CCCC4=CC=CC=C4

Appearance: 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: To be determined

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:         

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: RX-3117 inhibits DNA methyltransferase 1 (DNMT1). RX-3117 shows antiproliferative and anti-tumor activity. RX-3117 induces cell cycle arrest at S phase and apoptosis.
In vitro activity: This study identified which of the form of uridine-cytidine kinase (UCK), UCK1 or UCK2, is responsible for RX-3117 phosphorylation. Transfection of UCK2-siRNA effectively downregulated UCK2 expression and protected cells against RX-3117, indicating that UCK2 plays a crucial role in RX-3117 activation. RX-3117 is primarily activated by UCK2, offering a potential method for identifying patients who might benefit from RX-3117 treatment in clincal studies. Reference: PLoS One. 2016 Sep 9;11(9):e0162901. https://pubmed.ncbi.nlm.nih.gov/27612203/
In vivo activity: RX-3117 displayed promising anticancer activity in multiple human tumor xenograft models in mice, including gemcitabine-resistant tumors. RX-3117 outperformed gemcitabine in specific models, highlighting its potential as an effective alternative for cancer treatment, particularly in cases of gemcitabine resistance. Reference: Anticancer Res. 2014 Dec;34(12):6951-9. https://pubmed.ncbi.nlm.nih.gov/25503121/

Preparing Stock Solutions

The following data is based on the product molecular weight 257.22 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.

Recalculate based on batch purity %
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: 1. Sarkisjan D, Julsing JR, El Hassouni B, Honeywell RJ, Kathmann I, Matherly LH, Lee YB, Kim DJ, Peters GJ. RX-3117 (Fluorocyclopentenyl-Cytosine)-Mediated Down-Regulation of DNA Methyltransferase 1 Leads to Protein Expression of Tumor-Suppressor Genes and Increased Functionality of the Proton-Coupled Folate Carrier. Int J Mol Sci. 2020 Apr 14;21(8):2717. doi: 10.3390/ijms21082717. PMID: 32295203; PMCID: PMC7215832. 2. Sarkisjan D, Julsing JR, Smid K, de Klerk D, van Kuilenburg AB, Meinsma R, Lee YB, Kim DJ, Peters GJ. The Cytidine Analog Fluorocyclopentenylcytosine (RX-3117) Is Activated by Uridine-Cytidine Kinase 2. PLoS One. 2016 Sep 9;11(9):e0162901. doi: 10.1371/journal.pone.0162901. PMID: 27612203; PMCID: PMC5017758. 3. Babiker H, Schlegel PJ, Hicks LG, Bullock AJ, Burhani N, Mahadevan D, Elquza E, Borad MJ, Benaim E, Peterson C, Heaton C, Ocean AJ. A multicenter phase 1/2 study investigating the safety, pharmacokinetics, pharmacodynamics and efficacy of a small molecule antimetabolite, RX-3117, plus nab-paclitaxel in pancreatic adenocarcinoma. Invest New Drugs. 2022 Feb;40(1):81-90. doi: 10.1007/s10637-021-01164-9. Epub 2021 Aug 21. PMID: 34417914. 4. Yang MY, Lee YB, Ahn CH, Kaye J, Fine T, Kashi R, Ohne O, Smid K, Peters GJ, Kim DJ. A novel cytidine analog, RX-3117, shows potent efficacy in xenograft models, even in tumors that are resistant to gemcitabine. Anticancer Res. 2014 Dec;34(12):6951-9. PMID: 25503121.
In vitro protocol: 1. Sarkisjan D, Julsing JR, El Hassouni B, Honeywell RJ, Kathmann I, Matherly LH, Lee YB, Kim DJ, Peters GJ. RX-3117 (Fluorocyclopentenyl-Cytosine)-Mediated Down-Regulation of DNA Methyltransferase 1 Leads to Protein Expression of Tumor-Suppressor Genes and Increased Functionality of the Proton-Coupled Folate Carrier. Int J Mol Sci. 2020 Apr 14;21(8):2717. doi: 10.3390/ijms21082717. PMID: 32295203; PMCID: PMC7215832. 2. Sarkisjan D, Julsing JR, Smid K, de Klerk D, van Kuilenburg AB, Meinsma R, Lee YB, Kim DJ, Peters GJ. The Cytidine Analog Fluorocyclopentenylcytosine (RX-3117) Is Activated by Uridine-Cytidine Kinase 2. PLoS One. 2016 Sep 9;11(9):e0162901. doi: 10.1371/journal.pone.0162901. PMID: 27612203; PMCID: PMC5017758.
In vivo protocol: 1. Babiker H, Schlegel PJ, Hicks LG, Bullock AJ, Burhani N, Mahadevan D, Elquza E, Borad MJ, Benaim E, Peterson C, Heaton C, Ocean AJ. A multicenter phase 1/2 study investigating the safety, pharmacokinetics, pharmacodynamics and efficacy of a small molecule antimetabolite, RX-3117, plus nab-paclitaxel in pancreatic adenocarcinoma. Invest New Drugs. 2022 Feb;40(1):81-90. doi: 10.1007/s10637-021-01164-9. Epub 2021 Aug 21. PMID: 34417914. 2. Yang MY, Lee YB, Ahn CH, Kaye J, Fine T, Kashi R, Ohne O, Smid K, Peters GJ, Kim DJ. A novel cytidine analog, RX-3117, shows potent efficacy in xenograft models, even in tumors that are resistant to gemcitabine. Anticancer Res. 2014 Dec;34(12):6951-9. PMID: 25503121.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Peters GJ, Smid K, Vecchi L, Kathmann I, Sarkisjan D, Honeywell RJ, Losekoot N, Ohne O, Orbach A, Blaugrund E, Jeong LS, Lee YB, Ahn CH, Kim DJ. Metabolism, mechanism of action and sensitivity profile of fluorocyclopentenylcytosine (RX-3117; TV-1360). Invest New Drugs. 2013 Dec;31(6):1444-57. doi: 10.1007/s10637-013-0025-x. Epub 2013 Sep 19. PubMed PMID: 24048768.