WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H597222
CAS#: 137281-23-3 (free acid)
Description: Pemetrexed is a guanine-derived ANTINEOPLASTIC AGENT that functions as a NUCLEIC ACID SYNTHESIS INHIBITOR through its binding to, and inhibition of, THYMIDYLATE SYNTHASE.
Hodoodo Cat#: H597222
Name: Pemetrexed
CAS#: 137281-23-3 (free acid)
Chemical Formula: C20H21N5O6
Exact Mass: 427.15
Molecular Weight: 427.410
Elemental Analysis: C, 56.20; H, 4.95; N, 16.39; O, 22.46
Related CAS #: 357166-29-1 (sodium hydrate) 150399-23-8 (disodium) 137281-23-3 (free acid) 357166-30-4 (sodium 2.5 hydrate) 1851348-04-3 (tromethamine)
Synonym: Pemetrexed; Alimta; HSDB 7316; HSD-7316; HSDB7316;
IUPAC/Chemical Name: (4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoyl)-L-glutamic acid
InChi Key: WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
InChi Code: InChI=1S/C20H21N5O6/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)/t13-/m0/s1
SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(CCC2=CNC(NC(N)=N3)=C2C3=O)C=C1)=O
Appearance: Solid powder
Purity: >96% (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: Soluble in DMSO
Shelf Life: >3 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: 2934.99.03.00
More Info:
| Biological target: | Pemetrexed (LY231514) is an antifolate, the Ki values of the pentaglutamate of Pemetrexed (LY231514) are 1.3, 7.2, and 65 nM for inhibition of thymidylate synthase (TS), dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT), respectively. |
| In vitro activity: | In non-limited glucose condition, PEM (pemetrexed) alone led to the repression (72%) of protein synthesis confirming that the reduction in biomass in response to the drug could be attributed to the repression of protein translation. However, when PEM-treated cells were maintained in 1 mM glucose, the rate of protein synthesis was significantly higher than that in the glucose-starved condition alone. These results show that PEM treatment partially relieves translation inhibition caused by low glucose. Reference: Metabolites. 2021 Mar 26;11(4):198. https://pubmed.ncbi.nlm.nih.gov/33810430/ |
| In vivo activity: | To define an appropriate oral dose of PMX (pemetrexed)/DCK-OP, the tumor inhibitory effect thereof was assessed using the A549 xenograft mouse model. After 24 days of treatment, PMX/DCK-OP exhibited a dose-dependent tumor inhibitory effect; tumor volumes fell by 40.1, 57.2, and 64.2% when PMX/DCK-OP was given at 10, 20, and 40 mg/kg PMX, respectively, compared to the control group (p < 0.001) (Figure 6A). After treatment, all tumors were excised and weighed (Figure 6B). The tumor weight graph well-reflected the tumor volume results; dose-dependent inhibition of tumor volume was apparent. PMX/DCK-OP at 40 mg/kg PMX maximally reduced tumor weight (by 59.1%) compared to the control (p < 0.001) (Figure 6C). Reference: Pharmaceutics. 2019 Jul 13;11(7):332. https://pubmed.ncbi.nlm.nih.gov/31337061/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 125.9 | 294.60 |
The following data is based on the product molecular weight 427.41 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.
| 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. Piecyk M, Triki M, Laval PA, Dragic H, Cussonneau L, Fauvre J, Duret C, Aznar N, Renno T, Manié SN, Chaveroux C, FerraroPeyret C. Pemetrexed Hinders Translation Inhibition upon Low Glucose in Non-Small Cell Lung Cancer Cells. Metabolites. 2021 Mar 26;11(4):198. doi: 10.3390/metabo11040198. PMID: 33810430; PMCID: PMC8067050. 2. Li X, Song H, Kong F, Guo Y, Chen Y, Zhang L, Gao D, Zhao X, Zhang H. Pemetrexed exerts anticancer effects by inducing G0/G1-phase cell cycle arrest and activating the NOXA/Mcl-1 axis in human esophageal squamous cell carcinoma cells. Oncol Lett. 2019 Feb;17(2):1851-1858. doi: 10.3892/ol.2018.9753. Epub 2018 Nov 23. PMID: 30675247; PMCID: PMC6341790. 3. Maharjan R, Pangeni R, Jha SK, Choi JU, Chang KY, Choi YK, Park JW, Byun Y. Anti-Angiogenic Effect of Orally Available Pemetrexed for Metronomic Chemotherapy. Pharmaceutics. 2019 Jul 13;11(7):332. doi: 10.3390/pharmaceutics11070332. PMID: 31337061; PMCID: PMC6680992 |
| In vitro protocol: | 1. Piecyk M, Triki M, Laval PA, Dragic H, Cussonneau L, Fauvre J, Duret C, Aznar N, Renno T, Manié SN, Chaveroux C, FerraroPeyret C. Pemetrexed Hinders Translation Inhibition upon Low Glucose in Non-Small Cell Lung Cancer Cells. Metabolites. 2021 Mar 26;11(4):198. doi: 10.3390/metabo11040198. PMID: 33810430; PMCID: PMC8067050. 2. Li X, Song H, Kong F, Guo Y, Chen Y, Zhang L, Gao D, Zhao X, Zhang H. Pemetrexed exerts anticancer effects by inducing G0/G1-phase cell cycle arrest and activating the NOXA/Mcl-1 axis in human esophageal squamous cell carcinoma cells. Oncol Lett. 2019 Feb;17(2):1851-1858. doi: 10.3892/ol.2018.9753. Epub 2018 Nov 23. PMID: 30675247; PMCID: PMC6341790. |
| In vivo protocol: | 1. Maharjan R, Pangeni R, Jha SK, Choi JU, Chang KY, Choi YK, Park JW, Byun Y. Anti-Angiogenic Effect of Orally Available Pemetrexed for Metronomic Chemotherapy. Pharmaceutics. 2019 Jul 13;11(7):332. doi: 10.3390/pharmaceutics11070332. PMID: 31337061; PMCID: PMC6680992 |
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