Pemetrexed

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Cat.No. 6185 - Pemetrexed | C20H21N5O6 | CAS No. 137281-23-3
Description: Thymidylate synthetase inhibitor, also inhibits dihydrofolate reductase, GARFT and AICART
Chemical Name: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid
Purity: ≥98% (HPLC)
Datasheet
Citations
Reviews
Literature
Pathways

Biological Activity

High affinity dihydrofolate reductase inhibitor (Ki = 7 nM). Also inhibits thymidylate synthase, AICART and glycinamide ribonucleotide formyltransferase (Ki values are 109 nM, and 3.5 μM and 9.3 μM, respectively). Indirectly activates AMPK. Inhibits proliferation of cancer cell lines in vitro.

Technical Data

M. Wt 427.41
Formula C20H21N5O6
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 137281-23-3
PubChem ID 394493
InChI Key WBXPDJSOTKVWSJ-UHFFFAOYSA-N
Smiles NC1=NC(C2=C(N1)NC=C2CCC3=CC=C(C(N[C@H](C(O)=O)CCC(O)=O)=O)C=C3)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 42.74 100

Preparing Stock Solutions

The following data is based on the product molecular weight 427.41. Batch specific molecular weights may vary from batch to batch due to solvent 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 2.34 mL 11.7 mL 23.4 mL
5 mM 0.47 mL 2.34 mL 4.68 mL
10 mM 0.23 mL 1.17 mL 2.34 mL
50 mM 0.05 mL 0.23 mL 0.47 mL

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References

References are publications that support the biological activity of the product.

Shih et al (1997) LY231514, a pyrrolo[2,3-d]pyrimidine-based antifolate that inhibits multiple folate-requiring enzymes. Cancer Res. 57 1116 PMID: 9067281

Rothbart et al (2010) Pemetrexed indirectly activates the metabolic kinase AMPK in human carcinomas. Cancer Res. 70 10299 PMID: 21159649


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View all Thymidylate Synthetase Inhibitors

Keywords: Pemetrexed, Pemetrexed supplier, high, affinity, dihydrofolate, reductase, inhibitor, inhibitors, DHFR, thymidylate, synthase, TS, AICART, AICARFT, aminoimidazolecarboxamide, ribonucleotide, formyltransferase, glycinamide, GARFT, chemotherapeutic, antifolate, antimetabolite, Dihydrofolate, Reductase, Other, Transferases, Thymidylate, Synthetase, 6185, Tocris Bioscience

Citations for Pemetrexed

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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


Cancer Metabolism

Cancer Metabolism Poster

Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the main targets for cancer metabolism researchers. Genetic changes and epigenetic modifications in cancer cells alter the regulation of cellular metabolic pathways. These distinct metabolic circuits could provide viable cancer therapeutic targets.

Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.

Pathways for Pemetrexed

Apoptosis

Apoptosis Signaling Pathway

Apoptosis is a physiological process for cell death that is critical during aging and development. It may also be referred to as cell 'suicide'. Apoptosis can be triggered by events both inside and outside of the cell.
p53

p53 Signaling Pathway

p53 signaling plays an important role in the co-ordination of the cellular response different types of stress such as DNA damage and hypoxia. The downstream signals lead to apoptosis, senescence and cell cycle arrest.