137281-23-3 Usage
Description
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt, also known as Pemetrexed, is an N-acylglutamic acid with a specific N-acyl group. It is an antineoplastic agent that inhibits thymidylate synthase (TS), dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT). Pemetrexed is a pyrrolopyrimidine and a N-acyl-L-glutamic acid, and it is a conjugate acid of a pemetrexed(2-). It is an off-white solid and is marketed under the brand name Alimta by Eli Lilly and Company.
Uses
1. Used in Anticancer Applications:
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt is used as an antineoplastic agent for the treatment of malignant pleural mesothelioma (MPM) and various other cancers. It works by inhibiting key enzymes involved in DNA synthesis and function, thereby disrupting the rapid cell division and growth associated with cancer cells.
2. Used in Erectile Dysfunction Therapy:
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt is also used in the treatment of erectile dysfunction, where it may help improve blood flow and overall sexual function in men.
3. Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt is used as an active pharmaceutical ingredient in the development and production of drugs, specifically for cancer treatment and erectile dysfunction therapy.
4. Used in Research and Development:
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt is utilized in research and development for the study of its potential applications in various medical fields, including oncology and urology. Researchers may explore its mechanisms of action, potential synergistic effects with other drugs, and its role in targeted cancer therapies.
Side effects
The most common side effects for pemetrexed include fatigue, nausea, vomiting, anorexia, mucositis, myelosuppression ± infection, bleeding, rash, diarrhea and ↑ LFTs.Severe myelosuppression is often dose-limiting for pemetrexed. Sepsis, in some cases fatal, have occurred in approximately 1% of patients in clinical trials. Prophylactic folic acid and intramuscular vitamin B12 supplements are necessary to reduce hematologic or non-hematologic toxicities.Pemetrexed may cause serious and in some cases fatal dermatologic toxicities. Rarely, StevensJohnson syndrome and toxic epidermal necrolysis have been reported.
Mode of action
Pemetrexed is a pyrrolopyrimidine antifolate that exerts its antineoplastic activity by inhibiting thymidylate synthase (TS), glycinamide ribonucleotide formyltransferase (GARFT) and dihydrofolate reductase (DHFR), which are involved in folate metabolism and DNA synthesis, resulting in inhibition of purine and thymidine nucleotide synthesis.
Check Digit Verification of cas no
The CAS Registry Mumber 137281-23-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,7,2,8 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 137281-23:
(8*1)+(7*3)+(6*7)+(5*2)+(4*8)+(3*1)+(2*2)+(1*3)=123
123 % 10 = 3
So 137281-23-3 is a valid CAS Registry Number.
InChI:InChI=1/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
137281-23-3Relevant articles and documents
Pemetrexed - N, N - dibenzyl ethylenediamine salt preparation method (by machine translation)
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Paragraph 0029-0032; 0038-0039; 0044-0045; 0049-0050; 0055, (2017/11/16)
The invention relates to a pemetrexed - N, N - dibenzyl ethylenediamine salt preparation method, the pemetrexed - N, N - dibenzyl ethylenediamine salt of the chemical name is N - [4 - [2 - (2 - amino - 4, 7 - dihydro - 4 - oxo - 1 H - pyrrolo [2, 3 - d] - pyrimidin - 5 - yl) ethyl] benzoyl] - L - glutamic acid - N, N - dibenzyl ethylene glycol amine salt, the invention pemetrexed - N, N - dibenzyl ethylene diamine salt has good stability, can be water-free can also exist in the form of hydrate, and the pemetrexed - N, N - dibenzyl ethylenediamine salt in the prior art has not been reported, pemetrexed study for a dosage form provides a new selection; the invention pemetrexed - N, N - dibenzyl ethylenediamine salt preparation step of the method is simple and reasonable, the resulting product of the HPLC ≥ 99.70%, single impurity content is less than 0.1%, total mole yield of 75 - 80%. (by machine translation)
NEW CRYSTALLINE FORMS OF PEMETREXED DIACID, AND PREPARATIONS THEREOF
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Page/Page column 4, (2011/08/03)
Three new crystalline forms of pemetrexed diacid, preparation methods and uses thereof are disclosed. These preparation processes are simple and have better practicality.
Crystalline forms of pemetrexed diacid and processes for the preparation thereof
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Page/Page column 11, (2008/06/13)
Provided are crystalline forms of N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid, pemetrexed diacid, and processes for the preparation thereof.
