Pemetrexed disodiumTS, DHFR,GARFT and AICARFT inhibitor CAS# 150399-23-8 |
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| Cas No. | 150399-23-8 | SDF | Download SDF |
| PubChem ID | 125891 | Appearance | Powder |
| Formula | C20H19N5Na2O6 | M.Wt | 471.37 |
| Type of Compound | Miscellaneous | Storage | Desiccate at -20°C |
| Synonyms | LY231514 disodium | ||
| Solubility | H2O : ≥ 100 mg/mL (212.15 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | disodium;(2R)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioate | ||
| SMILES | C1=CC(=CC=C1CCC2=CNC3=C2C(=O)N=C(N3)N)C(=O)NC(CCC(=O)[O-])C(=O)[O-].[Na+].[Na+] | ||
| Standard InChIKey | NYDXNILOWQXUOF-FFXKMJQXSA-L | ||
| Standard InChI | InChI=1S/C20H21N5O6.2Na/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27;;/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29);;/q;2*+1/p-2/t13-;;/m1../s1 | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | 1. Pemetrexed disodium activates MEK/ERK-dependent cyto-protective autophagy, and inhibition of this pathway potentiates Pemetrexed disodium's activity in HepG2 cells. 2. Pemetrexed disodium is a multitargeted antifolate cytotoxic agent mainly used in lung cancer, is an antimetabolite drug, that inhibits enzymes involved in nucleotides bio-synthesis arresting cancer cells cycle. |
| Targets | MEK | ERK |
Pemetrexed disodium Dilution Calculator
Pemetrexed disodium Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1215 mL | 10.6074 mL | 21.2148 mL | 42.4295 mL | 53.0369 mL |
| 5 mM | 0.4243 mL | 2.1215 mL | 4.243 mL | 8.4859 mL | 10.6074 mL |
| 10 mM | 0.2121 mL | 1.0607 mL | 2.1215 mL | 4.243 mL | 5.3037 mL |
| 50 mM | 0.0424 mL | 0.2121 mL | 0.4243 mL | 0.8486 mL | 1.0607 mL |
| 100 mM | 0.0212 mL | 0.1061 mL | 0.2121 mL | 0.4243 mL | 0.5304 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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Pemetrexed (also known as pemetrexed disodium) is a novel antifolate antimetabolite targeting multiple enzymes involved in both pyrimidine and purine synthesis. Pemetrexed is an analog of the classic antifolate GARFYT inhibitor lometroxol with a similar chemical structure, where the pyrazine ring in the pterine portion of folic acid and the benzylic nitrogen in the bridge portion of folic acid are replaced by a pyrrole ring and a methylene group respectively. Pemetrexed potently inhibits TS, DHFR, and GARFT as well as AICARFT but with a lesser potency and exhibits autitumor activity in a broad range of tumors, including non-small cell lung carcinoma, malignant mesothelioma, and carcinomas of the breast, colorectum, uterine cervix, head and neck, and bladder.
Reference
Luis Paz-Ares, Susana Bezares, Jose M. Tabernero, Daniel Castellanos, and Hernan Cortes-Funes. Review of a promising new agent-pemetrexed disodium. Cancer 2003; 97(8 Suppl):2056-2063
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Inhibition of MEK/ERK activation attenuates autophagy and potentiates pemetrexed-induced activity against HepG2 hepatocellular carcinoma cells.[Pubmed:25446102]
Biochem Biophys Res Commun. 2015 Jan 2;456(1):86-91.
Identification of efficient chemo-therapeutic/chemo-preventive agents for treatment of hepatocellular carcinoma (HCC) is important. In this study, we examined the activity of pemetrexed, an anti-folate chemotherapy drug, against HepG2 human HCC cells. Pemetrexed treatment in vitro exerted weak but significant cytotoxic activity against HepG2 cells. When analyzing the possible pemetrexed-resistance factors, we indentified that pemetrexed treatment in HepG2 cells induced cyto-protective autophagy activation, evidenced by GFP-light chain 3B (LC3B) puncta formation, p62 downregulation and Beclin-1/LC3B-II upregulation. Correspondingly, autophagy inhibitors, including bafliomycin A1, 3-methyladenine and chloroquine, enhanced pemetrexed-induced cytotoxicity against HepG2 cells. Further, RNAi-mediated knockdown of Beclin-1 in HepG2 cells also increased pemetrexed sensitivity. Pemetrexed activated MEK (mitogen-activated protein kinase/ERK kinase)/ERK (extracellular-signal-regulated kinase) signaling in HepG2 cells, which was required for autophagy induction. Pharmacological inhibition of MEK/ERK activation attenuated pemetrexed-induced autophagy, enhanced HepG2 cell death and apoptosis. In summary, pemetrexed activates MEK/ERK-dependent cyto-protective autophagy, and inhibition of this pathway potentiates pemetrexed's activity in HepG2 cells.
Predictive role of erythrocyte macrocytosis during treatment with pemetrexed in advanced non-small cell lung cancer patients.[Pubmed:25870156]
Lung Cancer. 2015 Jun;88(3):319-24.
OBJECTIVES: Pemetrexed has been approved for the treatment of advanced non-small cell lung cancer (NSCLC) non-squamous histology, both as first- and second-line therapy. Pemetrexed is an antimetabolite drug, that inhibits enzymes involved in nucleotides bio-synthesis arresting cancer cells cycle. The aim of this study was the evaluation of the impact of pemetrexed on erythrocyte mean corpuscular volume (MCV) change and its possible correlation with disease control rate (DCR), progression free (PFS) and overall survival (OS) in NSCLC patients. MATERIALS AND METHODS: A retrospective collection of clinical and laboratory data (including basal MCV and maximum MCV occurred during therapy) in advanced NSCLC patients treated with pemetrexed at seven Italian centers was performed. Nonparametric tests, univariate and multivariate analysis were used to assess correlation between variables and to identify predictors of outcomes. RESULTS: 191 patients were enrolled: median age 62, 60% male, 61% performance status (PS) 0, 91% stage IV, 88% adenocarcinoma histotype, 25% never smoker, 62% received pemetrexed as first-line. Mean MCV significantly increased from basal (89fL) to during treatment (94fL), with mean DeltaMCV=4fL. The median time from therapy start to maximum MCV was 2.2 months. Median PFS was 7 [CI95% 6-8] and 3 [CI95% 2-4] months [P=0.0016], and median survival was 17 [CI95% 12-23] and 10 [CI95% 8-12] months [P=0.02], in patients with DeltaMCV>5fL (n=80) and DeltaMCV/=62, PS 0, adenocarcinoma histology and DeltaMCV>5fL as independent predictors of longer PFS. A DeltaMCV>5fL significantly correlates with DCR. CONCLUSION: Pemetrexed induces macrocytosis. DeltaMCV>5fL on pemetrexed therapy correlated with better DCR, PFS and OS. These results deserve further validation in prospective studies.
Pemetrexed disodium in ovarian cancer treatment.[Pubmed:22324304]
Expert Opin Investig Drugs. 2012 Apr;21(4):437-49.
INTRODUCTION: Current therapies for recurrent ovarian cancer (OC) yield relatively modest improvements in survival. Many drugs are available but recently a renewed interest is addressed on antimetabolite drugs. Pemetrexed (PEM) is a multitargeted antifolate cytotoxic agent mainly used in lung cancer. AREAS COVERED: This review summarizes the available evidence on the use of PEM in the treatment of OC. This article consists of material obtained via Medline, PubMed and EMBASE literature searches, up to November 2011. Currently available published data on mechanism of action, pharmacokinetics, safety and efficacy of PEM in the treatment of recurrent OC are described. EXPERT OPINION: Eight trials evaluated the use of PEM in OC patients. Studies using PEM in combination with carboplatin in platinum-sensitive OC suggested that the response rate is similar to other combination therapies. However, based on the absence of randomized trials comparing this doublet with currently used combination treatments, it is difficult to draw conclusions on the efficacy of PEM regimens in these patients. In platinum-resistant OC patients, two studies suggested that PEM alone might have equivalent activity to other single-agent treatment. Further pharmacogenomic and clinical data are warranted to better define the role of PEM in the treatment of recurrent OC.
Synthesis and physicochemical characterization of the impurities of pemetrexed disodium, an anticancer drug.[Pubmed:26035100]
Molecules. 2015 May 29;20(6):10004-31.
A physicochemical characterization of the process-related impurities associated with the synthesis of Pemetrexed disodium was performed. The possibility of pemetrexed impurities forming has been mentioned in literature, but no study on their structure has been published yet. This paper describes the development of the synthesis methods for these compounds and discusses their structure elucidation on the basis of two-dimensional NMR experiments and MS data. The identification of these impurities should be useful for the quality control during the production of the Pemetrexed disodium salt.
