165049-28-5 Usage
Description
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate, also known as Pemetrexed, is a synthetic antifolate compound with potent antineoplastic activity. It is a pink powder that inhibits multiple enzymes involved in the synthesis of nucleotides, thereby disrupting DNA replication, repair, and function, leading to cell cycle arrest and apoptosis in cancer cells.
Uses
Used in Oncology:
Pemetrexed is used as an antineoplastic agent for the treatment of malignant pleural mesothelioma (MPM), a rare and aggressive form of cancer that affects the lining of the lungs and chest cavity. It is also used in combination with other chemotherapy drugs for the treatment of non-small cell lung cancer (NSCLC) and other solid tumors.
Used in Drug Formulation:
Pemetrexed is formulated as a diethyl ester prodrug to improve its solubility and bioavailability. The 1,5-diethyl ester group enhances the compound's lipophilicity, allowing for better absorption and distribution in the body. Once inside the cells, the ester group is cleaved, releasing the active Pemetrexed molecule.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Pemetrexed is used as an active pharmaceutical ingredient (API) in the development of cancer therapeutics. Its unique mechanism of action and ability to target multiple enzymes make it a valuable addition to the arsenal of cancer treatments.
Used in Research:
Pemetrexed is also used in research settings to study the molecular mechanisms of action of antifolate compounds and their potential applications in cancer therapy. It serves as a valuable tool for understanding the role of folate metabolism in cancer cell growth and survival.
Check Digit Verification of cas no
The CAS Registry Mumber 165049-28-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,5,0,4 and 9 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 165049-28:
(8*1)+(7*6)+(6*5)+(5*0)+(4*4)+(3*9)+(2*2)+(1*8)=135
135 % 10 = 5
So 165049-28-5 is a valid CAS Registry Number.
InChI:InChI=1/C24H29N5O6.C7H8O3S/c1-3-34-18(30)12-11-17(23(33)35-4-2)27-21(31)15-8-5-14(6-9-15)7-10-16-13-26-20-19(16)22(32)29-24(25)28-20;1-6-2-4-7(5-3-6)11(8,9)10/h5-6,8-9,13,17H,3-4,7,10-12H2,1-2H3,(H,27,31)(H4,25,26,28,29,32);2-5H,1H3,(H,8,9,10)/t17-;/m0./s1
165049-28-5Relevant articles and documents
Method for preparing pemetrexed disodium at high yield
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Page/Page column 9-13, (2021/01/12)
The invention relates to a preparation method of pemetrexed disodium. The preparation method is characterized in that an alkali-modified microporous/mesoporous molecular sieve catalyst is used as a catalyst to replace NaOH as a reaction catalyst, so favorable yield and product purity are obtained under the condition of enlarged reaction scale.
Pemetrexed disodium intermediate and preparation method thereof
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Paragraph 0097-0100, (2019/10/17)
The invention belongs to the technical field of medicines, and particularly relates to a pemetrexed disodium intermediate II and a preparation method thereof. The preparation method includes the steps: adding 4-[2-(2-amino-4, 7-dihydro-4-oxygen-3H-pyrrolo[2, 3-d] pyrimidine-5-group) ethyl] benzoic acid into DMF (dimethyl formamide) and triethylamine; performing stirring and dissolving; dropping R-CL; performing heat preservation reaction; drying the DMF by distillation in a pressure reducing manner; adding pure water to stir mixture; adjusting pH (potential of hydrogen) by diluted hydrochloricacid to reach 5-6; performing stirring, crystallizing, extracting, filtering and drying to obtain the intermediate II. Preparation of the intermediate II is simpler, amidogen is protected, impuritiesV generated by self-reaction are avoided, the problems of oxidation and discoloration caused by amidogen instability in reaction process are prevented, conditions are mild, yield is high, a product is stable, and practical production is facilitated.
METHOD FOR PREPARING AN INTERMEDIATE FOR PRODUCING HIGH-PURITY PEMETREXED AND METHOD FOR PRODUCING HIGH-PURITY PEMETREXED USING THE INTERMEDIATE
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Paragraph 0079, (2016/08/17)
Disclosed are a method for preparing an intermediate for producing high-purity pemetrexed and a method for producing high-purity pemetrexed using the intermediate, and more specifically, a method for preparing pemetrexed diethyl ester, which is an intermediate for producing pemetrexed, or a salt thereof with high purity, and to a method for producing pemetrexed disodium salt with high purity using the intermediate.