CAS: 869791-42-4; (S)-2-(4-(2-(2-Amino-1-Methyl-4-Oxo-4,7-Dihydro-1H-Pyrrolo[2,3-D]Pyrimidin-5-yl)Ethyl)Benzamido)Pentanedioic Acid

该化合物是一种化学化合物,通常与制药工业有关,特别是在癌症治疗方面,是一种杂质,与某些类型癌症,包括间皮瘤和非小型细胞肺癌的化疗中多目标抗化剂相干,其特征可能包括其分子结构,可能与微粒结构相类似,但略有变化,影响其药理特性.PeMetrexed EDP杂质A等杂质通常以其溶性,稳定性和潜在的生物活动为特征,这些杂质可能影响药物制剂的总体功效和安全性.监管准则通常要求查明和量化这种杂质,以确保药品的质量和安全.了解杂质的特性对于制药工业的药物开发和质量控制过程至关重要.

英文名称(S)-2-(4-(2-(2-Amino-1-Methyl-4-Oxo-4,7-Dihydro-1H-Pyrrolo[2,3-D]Pyrimidin-5-yl)Ethyl)Benzamido)Pentanedioic Acid
中文名称N-甲基培美曲塞
IUPAC名称(4-(2-(2-amino-1-methyl-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoyl)-L-glutamic acid
其它别名Pemetrexed Ep Impurity A; N-Methyl Pemetrexed; Pemetrexed Impurity; Jkulrgfpybajte-Aweznqclsa-N; Pemetrexed Disodium Ep Impurity A; Pemetrexed Impurity 2(Pemetrexed Ep Impurity A); (Sodium (S)-2-(4-(2-(2-Amino-1-Methyl; Pemetrexed Impurity 1/pemetrexed Ep Impurity A/(4-(2-(2-Amino-1-Methyl-4-Oxo-4,7-Dihydro-1H-Pyrrolo[2,3-D]Pyrimidin-5-yl)Ethyl)Benzoyl)-L-Glutamic Acid
CAS编号869791-42-4
MFCD编号:MFCD34471012
EINECS号:805-166-5
FDA UNII编号:QDJ47U4SYL
分子式:C21H23N5O6
分子量:441.44
产品CID: 1873784
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: JKULRGFPYBAJTE-AWEZNQCLSA-N
InChI=1S/C21H23N5O6/c1-26-17-16(19(30)25-21(26)22)13(10-23-17)7-4-11-2-5-12(6-3-11)18(29)24-14(20(31)32)8-9-15(27)28/h2-3,5-6,10,14,23H,4,7-…
计算化学: 氢键受体数6.0氢键供体数5.0可旋转键数9.0

物理性质

熔点>208°C (分解)
密度1.52±0.1 g/cm3(预测)
pKa:3.58±0.10(预测)
LogP:0.4
溶解性Basic Alcohol (Slightly), DMSO (Slightly), Water (Slightly, Heated)
外观形态白色至浅紫色固体
储存条件防潮, 冰箱, 置于惰性气氛下
产品应用该化合物用作癌症研究的抗泡沫细胞毒剂.

MSDS等安全信息

GHS象形图
GHS符号GHS08 & GHS07;
注释: Health hazard & Exclamation mark
危险类别致突变性类别2
生殖毒性类别1B
特定目标器官毒性-重复接触类别2
皮肤腐蚀/刺激类别2
严重眼刺激类别2
警示词Danger(危险)
危险描述H341 |怀疑导致遗传缺陷.
H360 |可能损害生育能力或胎儿.
H373 |长期或反复接触可能损害器官.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P201-P202-P281-P308+P313-P405-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P260-P314-P501
安全声明H303+H313+H333

欧盟法规

ECHA物质C&L通报

上下游产品

diethyl-L-glutamate hydr°Chloride 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid methyl iodide N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 4-methylbenzenesulfonic acid salt

合成工艺路线路线简述

869791-50-4 = 869791-42-4
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 2 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3.0
标题:Synthesis And Physicochemical Characterization Of The Impurities Of Pemetrexed Disodium,An Anticancer Drug
作者:Michalak,Olga; Et Al
参考文献:Molecules 日期:2015 卷标:20(6) 页码:10004-10031]

357166-29-1 = 869791-42-4
反应条件:1.1 Reagents: Triethylamine Solvents: Dimethylformamide; 40 H,24 °C1.2 Reagents: Sodium Hydroxide Solvents: Water; 30 Min,24 °C1.3 Reagents: Hydrochloric Acid Solvents: Ethanol,Water; Ph 3.5
标题:Determination Of The Source Of The N-Methyl Impurity In The Synthesis Of Pemetrexed Disodium Heptahydrate
作者:Kjell,Douglas P.; Et Al
参考文献:Organic Process Research & Development 日期:2005 卷标:9(6) 页码:738-742]

104-15-4 + 146943-43-3 = 869791-42-4
反应条件:1.1 Reagents: Triethylamine Solvents: Dimethylformamide; 72 H,Rt2.1 Reagents: Sodium Hydroxide Solvents: Water; 2 H,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3.0
标题:Synthesis And Physicochemical Characterization Of The Impurities Of Pemetrexed Disodium,An Anticancer Drug
作者:Michalak,Olga; Et Al
参考文献:Molecules 日期:2015 卷标:20(6) 页码:10004-10031]

104-15-4 + 1118-89-4 + 1209465-70-2 = 869791-42-4
反应条件:1.1 2 H1.2 Reagents: Water; 15 Min1.3 Solvents: Ethanol; 2 H,Reflux2.1 Reagents: Triethylamine Solvents: Dimethylformamide; 72 H,Rt3.1 Reagents: Sodium Hydroxide Solvents: Water; 2 H,Rt3.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3.0
标题:Synthesis And Physicochemical Characterization Of The Impurities Of Pemetrexed Disodium,An Anticancer Drug
作者:Michalak,Olga; Et Al
参考文献:Molecules 日期:2015 卷标:20(6) 页码:10004-10031]

3140-73-6 + 137281-39-1 = 869791-42-4
反应条件:1.1 Reagents: 4-Methylmorpholine Solvents: Dimethylformamide,Dichloromethane; 2 H,38 - 40 °C2.1 2 H2.2 Reagents: Water; 15 Min2.3 Solvents: Ethanol; 2 H,Reflux3.1 Reagents: Triethylamine Solvents: Dimethylformamide; 72 H,Rt4.1 Reagents: Sodium Hydroxide Solvents: Water; 2 H,Rt4.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3.0
标题:Synthesis And Physicochemical Characterization Of The Impurities Of Pemetrexed Disodium,An Anticancer Drug
作者:Michalak,Olga; Et Al
参考文献:Molecules 日期:2015 卷标:20(6) 页码:10004-10031

(2S)-2-[[4-[2-(2-Amino-1-Methyl-4-Oxo-4,7-Dihydro-1H-Pyrrolo[2,3-D]Pyrimidin-5-yl)Ethyl]Benzoyl]Amino]Pentanedioic Acid Diethyl Ester置于sodium Hydroxide体系中,用水作为反应溶剂,化学反应 2.0H,以81%的收率获得产物n-甲基培美曲塞
参考文献:抗癌药物培美曲塞二钠杂质的合成及理化表征
标题:抗癌药物培美曲塞二钠杂质的合成及理化表征
摘要:对与培美曲塞二钠合成相关的工艺相关杂质进行了物理化学表征.文献中已经提到形成培美曲塞杂质的可能性,但尚未发表对其结构的研究.本文描述了这些化合物的合成方法的发展,并讨论了基于二维 NMR 实验和 Ms 数据的结构解析.这些杂质的鉴定应有助于培美曲塞二钠盐生产过程中的质量控制.
DOI:10.3390/molecules200610004