Raltitrexed (ZD1694)

Alias: ZD-1694; ICID1694; ZD1694; D1694; ICI-D1694; D-1694; D 1694; ICID 1694; ZD 1694; TDX; trade name: Tomudex.
Cat No.:V1473 Purity: =99.03%
Raltitrexed (formerly Thaltitrexed; ICID1694; TDX; ZD-1694; D1694; ICI-D1694; trade name: Tomudex),a quinazoline folate analog, is an approved antimetabolite anticancer drug used in cancer chemotherapy for treating colorectal cancer and malignant mesothelioma.
Raltitrexed (ZD1694) Chemical Structure CAS No.: 112887-68-0
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: =99.03%

Product Description

Raltitrexed (formerly Thaltitrexed; ICID1694; TDX, ZD-1694; D1694; ICI-D1694; trade name: Tomudex), a quinazoline folate analog, is an approved antimetabolite anticancer drug used in cancer chemotherapy for treating colorectal cancer and malignant mesothelioma. Raltitrexed inhibits the growth of L1210 cells by acting as a thymidylate synthase inhibitor, with an IC50 of 9 nM.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

Raltitrexed inhibits HepG2 growth by stopping the cell cycle at G0/G1, which is achieved by downregulating CDK2 and cyclin A[1]. The viability of SGC7901 cells is decreased by raltitrexed (0.1, 0.5, and 2.5 μg/mL) in a manner that is dependent on both dose and time. In SGC7901 cells, raltitrexed (0.5 μg/mL) exhibits characteristic apoptotic morphology, such as nuclear shrinkage, fragmentation, chromatin condensation, and apoptotic bodies. Raltitrexed lowers the potential of the mitochondrial membrane and stops the cell cycle at the G0/G1 phase. In addition, Raltitrexed raises TS protein and mRNA expression levels, triggers caspase-3-dependent apoptosis by activating the mitochondria, and raises ROS levels[3]. Raltitrexed (1.5 nM) selectively induces gene conversions and decreases the number of GM00637 cells, but it has no effect on NHEJ or HR induced by DSB[4].

ln Vivo
Raltitrexed (0, 5, 10, 11.5, 13.5, 15 mg/kg b/w, i.p.) raises the rates of resorbed embryos and growth retardation of the murine model of NTDs in a dose dependent manner. Thymidylate synthase (TS) activity in embryonic tissue is maximally inhibited by raltitrexed (11.5 mg/kg b/w), which also lowers dTMP levels and raises dUMP levels[2].
Cell Assay
GM00637 cells are plated at a density of 3.3×105 cells per 25 cm2 flask in order to evaluate the impact of Raltitrexed on cell viability and/or growth. After 24 hours, the medium is swapped out for one supplemented with different amounts of Raltitrexed, which are present in a wide range of concentrations, from less than 1 nM to more than 1 µM. For each dosage that is tested, three cell flasks are used. The cells are refed with medium that does not contain Raltitrexed after being exposed to it for 24 hours. Cells are collected and tallied 48 hours following drug-free medium feeding. The impact of Raltitrexed on cell viability and/or growth rate is measured by comparing the cell counts of the exposed cells to the control cells that were not exposed to Raltitrexed at different doses.
Animal Protocol
The experiment uses adult C57BL/6 mice weighing 19–20 g at 7-8 weeks of age. Mice are kept at 22°C with a 12-hour light/dark cycle. They are given unlimited access to tap water and regular mouse chow. The male and female mice mate overnight, and the next morning, the vaginal plugs are checked. Gestational day 0.5 is when the vaginal plug is present in the pregnant mice. Six groups of ten pregnant mice each are created at random. On gestational day 7.5, five groups receive intraperitoneal injections of varying doses of Raltitrexed (5, 10, 11.5, 13.5, and 15 mg/kg b/w). Raltitrexed is dissolved in 0.99% NaCl. On day 7.5 of gestation, the control group receives an intraperitoneal injection of 0.9% NaCl at the same volume. Pregnant mice are slaughtered on gestational day 11.5 and the embryos are studied under a dissecting microscope.
References

[1]. Raltitrexed Inhibits HepG2 Cell Proliferation via G0/G1 Cell Cycle Arrest. Oncol Res. 2016;23(5):237-48.

[2]. Raltitrexed's effect on the development of neural tube defects in mice is associated with DNA damage, apoptosis, and proliferation. Mol Cell Biochem. 2015 Jan;398(1-2):223-31.

[3]. Raltitrexed induces mitochondrial-mediated apoptosis in SGC7901 human gastric cancer cells. Mol Med Rep. 2014 Oct;10(4):1927-34.

[4]. Induction of intrachromosomal homologous recombination in human cells by raltitrexed, an inhibitor of thymidylate synthase. DNA Repair (Amst). 2008 Oct 1;7(10):1624-35.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H22N4O6S
Molecular Weight
458.49
Exact Mass
458.13
Elemental Analysis
C, 55.01; H, 4.84; N, 12.22; O, 20.94; S, 6.99
CAS #
112887-68-0
Appearance
Solid powder
SMILES
CC1=NC2=C(C=C(C=C2)CN(C)C3=CC=C(S3)C(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)N1
InChi Key
IVTVGDXNLFLDRM-HNNXBMFYSA-N
InChi Code
InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1
Chemical Name
(2S)-2-[[5-[methyl-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid
Synonyms
ZD-1694; ICID1694; ZD1694; D1694; ICI-D1694; D-1694; D 1694; ICID 1694; ZD 1694; TDX; trade name: Tomudex.
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~92 mg/mL (~200.7 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1811 mL 10.9054 mL 21.8107 mL
5 mM 0.4362 mL 2.1811 mL 4.3621 mL
10 mM 0.2181 mL 1.0905 mL 2.1811 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT06118762 Recruiting Drug: Fruquintinib Metastatic Colorectal Cancer The First Affiliated Hospital
of Nanchang University
October 20, 2023 Phase 4
NCT05426811 Not yet recruiting Drug: Regorafenib
Drug: Raltitrexed
Regorafenib
Raltitrexed
China Medical University, China July 1, 2022 Phase 1
Phase 2
NCT05148143 Active
Recruiting
Drug: Raltitrexed combined
with oxaplatin
Cholangioadenoma Second Affiliated Hospital,
School of Medicine, Zhejiang
University
June 1, 2020 Phase 2
NCT05160896 Recruiting Drug: Raltitrexed
Drug: Irinotecan
Advanced Metastatic Colorectal
Cancer
Second Affiliated Hospital,
School of Medicine, Zhejiang
University
November 12, 2021 Phase 2
NCT05231382 Recruiting Procedure: Oxaliplatin,
fluorouracil/leucovorin
(FOLFOX) treatment
Hepatocellular Carcinoma Sun Yat-sen University March 28, 2022 Phase 3
Biological Data
  • Effect of raltitrexed on inhibition rate in SGC7901 cells. Mol Med Rep . 2014 Oct;10(4):1927-34.
  • Effect of raltitrexed on apoptosis and cell cycle in SGC7901 cells. Mol Med Rep. 2014 Oct;10(4):1927-34.
  • Effect of raltitrexed on the expression of the apoptosis regulators in SGC7901 cells. Mol Med Rep . 2014 Oct;10(4):1927-34.
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