2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid hydrate

• ChemBase编号: 134377
• 分子式: C20H24N8O6
• 平均质量: 472.45456
• 单一同位素质量: 472.18188053
• SMILES: CN(Cc1cnc2c(n1)c(nc(n2)N)N)c1ccc(cc1)C(=O)NC(CCC(=O)O)C(=O)O.O
• Canonical SMILES: OC(=O)CCC(C(=O)O)NC(=O)c1ccc(cc1)N(Cc1cnc2c(n1)c(N)nc(n2)N)C.O
• InChI: InChI=1S/C20H22N8O5.H2O/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30;/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27);1H2
• InChIKey: FPJYMUQSRFJSEW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid hydrate
• IUPAC传统名: hydrate methotrexate
• 别名: 氨甲叶酸; 氨甲喋呤; DL-4-Amino-N10-methylpteroylglutamic acid; MTX; (±)Amethopterin hydrate

登记号

• CAS号: 60388-53-6(anhydrous)
• EC号: 262-213-7
• MDL号: MFCD00150845
• PubChem SID: 24891167; 162228653
• PubChem CID: 24207740

理论计算性质

• Acid pKa: 3.2608879
• 质子受体: 12
• 质子供体: 5
• LogD (pH = 5.5): -3.640823
• LogD (pH = 7.4): -6.5636883
• Log P: -0.23654379
• 摩尔折射率: 119.2108 cm^3
• 极化性: 43.521362 Å^3
• 极化表面积: 210.54 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: H2O: insoluble; NaOH: soluble (minimal amount of 0.1 N NaOH to solubilize, then dilute in neutral buffer or saline)
• 外观: yellow to yellow with an orange cast powder

安全信息

• RTECS编号: MA1224100
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 1544
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 61-25-36/38
• 安全公开号: 53-26-36/37-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H360
• GHS警示性声明: P201-P301 + P310-P305 + P351 + P338-P308 + P313
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... DHFRP1(573971), FPGS(2356), SLC19A1(6573), TYMS(7298)mouse ... Dhfr(13361)rat ... Dhfr(24312)

产品相关信息

• 纯度: ≥95%

详细说明

Sigma Aldrich - A7019

包装
25 mg in poly bottle
500 mg in glass bottle
Reconstitution
Add a minimal amount of 0.1 N NaOH to solubilize, then dilute in neutral buffer or saline. Diluted stock is stable for 1 week refrigerated and for 1 month frozen at -20 °C. References: Cell & Tissue Culture: Laboratory Procedures, Chapter 27, Page 27D:3.2 (A. Doyle, et al., eds, John Wiley) and Cell Biology: A Laboratory Handbook, vol. 2, page 417 (Julio E. Celis, ed., Academic Press).
Application
Amethopterin is a folic acid antagonist and potent anticancer agent. Amethopterin blocks DNA synthesis by preventing the production of tetrahydrofolate cofactors which are required to make thymidine. Amethopterin is actively transported into cells by the folate transporter where it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase, a dihydrofolate reductase inhibitor.
Biochem/physiol Actions
Amethopterin is a folic acid antagonist and potent anticancer agent. Blocks DNA synthesis by blocking the production of tetrahydrofolate covactors required for the synthesis of thymidine. Amethopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Amethopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.