(2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid

• ChemBase编号: 128251
• 分子式: C13H18Cl2N2O2
• 平均质量: 305.20022
• 单一同位素质量: 304.07453319
• SMILES: c1cc(ccc1C[C@@H](C(=O)O)N)N(CCCl)CCCl
• Canonical SMILES: ClCCN(c1ccc(cc1)C[C@@H](C(=O)O)N)CCCl
• InChI: InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
• InChIKey: SGDBTWWWUNNDEQ-LBPRGKRZSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-{4-[bis(2-chloroethyl)amino]phenyl}propanoic acid
• IUPAC传统名: melphalan
• 商标名: Alkeran
• 别名: p-Di-(2-chloroethyl)amino-L-phenylalanine; Alanine Nitrogen Mustard; Melfalan; Alkeran; Sarcoclorin; 2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]-propanoic acid; Melphalan; 4-[Bis(2-chloroethyl)amino]-L-phenylalanine; L-PAM; L-Phenylalanine mustard; Melphalan

登记号

• CAS号: 148-82-3
• EC号: 205-726-3
• MDL号: MFCD00057717
• Beilstein号: 2816456
• PubChem SID: 162222560; 24278538
• PubChem CID: 4053; 460612
• CHEBI ID: 28876
• ATC码: L01AA03
• CHEMBL: 852
• Chemspider ID: 405297
• DrugBank ID: DB01042
• KEGG ID: D00369
• 美国药典/FDA物质标识码: Q41OR9510P
• 维基百科标题: Melphalan
• Medline Plus: a682220

理论计算性质

• Acid pKa: 1.2884431
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 0.25192413
• LogD (pH = 7.4): 0.2493237
• Log P: 0.25219622
• 摩尔折射率: 78.2315 cm^3
• 极化性: 30.09238 Å^3
• 极化表面积: 66.56 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 95% ethanol and 1 drop 6 N HCl: soluble0.05 g/mL, clear; DMSO; Ethanol; Methanol; Propylene Glycol
• 外观: Off-White Solid; white powder
• 熔点: ~180 °C; 165-167°C (dec.)

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: AY3675000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2811
• 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: 45-46-26/27/28-63; 45-46-63-26/27/28
• 安全公开号: 53-22-36/37/39-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330-H350-H361
• GHS警示性声明: P201-P260-P264-P280-P284-P302 + P350
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

药理学性质

• 给药途径: Oral, intravenous
• 生物利用度: 25% to 89%
• 排泄: Renal, significantly metabolised
• 半衰期: 1.5 ± 0.8 hours
• 代谢: hydrolysis
• 法定药品分级: Rx-only

产品相关信息

• 纯度: ≥90% (TLC)
• 杂质: ≤10% water
• Empirical Formula (Hill Notation): C13H18Cl2N2O2

详细说明

Sigma Aldrich - M2011

Biochem/physiol Actions
Melphalan is an antineoplastic agent.1,2 It forms DNA intrastrand crosslinks by bifunctional alkylation in 5′-GGC sequences.3

Sigma Aldrich - 63648

Other Notes
Mechanisms of DNA sequence selective alkylation of guanine-N7 positions by nitrogen mustards1; Review2

Toronto Research Chemicals - M216900

Antineoplastic.

参考文献

• Ross, W.C.J., et al.: Biochem. Pharmacol., 13, 969 (1964)
• Donelli, M.G., et al.: J. Pharm. Pharmacol., 18, 760 (1964)
• Furner, R.L., et al.: Cancer Treat. Rep., 64, 559 (1964)