(2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid

• ChemBase编号: 524
• 分子式: C20H21N5O6
• 平均质量: 427.41064
• 单一同位素质量: 427.14918342
• SMILES: O=c1nc([nH]c2[nH]cc(CCc3ccc(cc3)C(=O)N[C@H](CCC(=O)O)C(=O)O)c12)N
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N
• InChI: 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-/m1/s1
• InChIKey: WBXPDJSOTKVWSJ-CYBMUJFWSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid
• IUPAC传统名: alimta; pemetrexed
• 商标名: Alimta
• 别名: LY231514; Pemetrexed Disodium; Pemetrexed; (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid

登记号

• CAS号: 137281-23-3; 150399-23-8
• MDL号: MFCD19105065
• PubChem SID: 160963987; 46505640
• PubChem CID: 60843

理论计算性质

JChem

• Acid pKa: 3.341115
• 质子受体: 9
• 质子供体: 6
• LogD (pH = 5.5): -2.0354736
• LogD (pH = 7.4): -5.047953
• Log P: 1.4881234
• 摩尔折射率: 109.4496 cm^3
• 极化性: 40.419224 Å^3
• 极化表面积: 186.97 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 0.11
• LOG S: -3.97
• 溶解度: 4.55e-02 g/l

分子性质

理化性质

• 疏水性(logP): -1.5

产品相关信息

• 纯度: 95+%

详细说明

DrugBank - DB00642

• Drug Groups: approved; investigational
• Description: Pemetrexed (brand name Alimta?) is a chemotherapy drug manufactured and marketed by Eli Lilly and Company. Its indications are the treatment of pleural mesothelioma as well as non-small cell lung cancer.
• Indication: Used in combination with cisplatin for the treatment of malignant pleural mesothelioma in adults whose disease is unresectable or who otherwise are not candidates for potentially curative surgery. Also used as a monotherapy for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) after prior chemotherapy
• Pharmacology: Preclinical studies have shown that pemetrexed inhibits the in vitro growth of mesothelioma cell lines (MSTO-211H, NCI-H2052). Studies with the MSTO-211H mesothelioma cell line showed synergistic effects when pemetrexed was combined concurrently with cisplatin.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized by Cytochrome P450 Enzymes
• Half Life: 3.5 hours
• Protein Binding: 81%
• Elimination: Pemetrexed is not metabolized to an appreciable extent and is primarily eliminated in the urine, with 70% to 90% of the dose recovered unchanged within the first 24 hours following administration.
• Distribution: * 16.1 L
• Clearance: * 91.8 mL/min [Cancer patients with normal renal function receiving 0.2 to 838 mg/m2 infusion over a 10-minute period]
• References: Rollins KD, Lindley C: Pemetrexed: a multitargeted antifolate. Clin Ther. 2005 Sep;27(9):1343-82. [Pubmed] ; Lansiaux A, Lokiec F: [Pemetrexed: from preclinic to clinic] Bull Cancer. 2007;94 Spec No Actualites:S134-8. [Pubmed] ; Fuld AD, Dragnev KH, Rigas JR: Pemetrexed in advanced non-small-cell lung cancer. Expert Opin Pharmacother. 2010 Jun;11(8):1387-402. [Pubmed] ; Adjei AA: Pemetrexed (Alimta): a novel multitargeted antifolate agent. Expert Rev Anticancer Ther. 2003 Apr;3(2):145-56. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Rollins KD, Lindley C: Pemetrexed: a multitargeted antifolate. Clin Ther. 2005 Sep;27(9):1343-82. Pubmed
• Lansiaux A, Lokiec F: [Pemetrexed: from preclinic to clinic] Bull Cancer. 2007;94 Spec No Actualites:S134-8. Pubmed
• Fuld AD, Dragnev KH, Rigas JR: Pemetrexed in advanced non-small-cell lung cancer. Expert Opin Pharmacother. 2010 Jun;11(8):1387-402. Pubmed
• Adjei AA: Pemetrexed (Alimta): a novel multitargeted antifolate agent. Expert Rev Anticancer Ther. 2003 Apr;3(2):145-56. Pubmed