hydrate hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase编号: 154522
• 分子式: C21H48NO5P
• 平均质量: 425.583281
• 单一同位素质量: 425.32701027
• SMILES: CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C.O
• Canonical SMILES: CCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-].O
• InChI: InChI=1S/C21H46NO4P.H2O/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4;/h5-21H2,1-4H3;1H2
• InChIKey: NTMJUKLGQGDYOT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: hydrate hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC传统名: hydrate miltex
• 别名: Choline hexadecyl phosphate; HePC; Hexadecyl phosphocholine; Impavido; Miltex; Miltefosine hydrate

登记号

• MDL号: MFCD12828861
• PubChem SID: 162248661
• PubChem CID: 71311890

理论计算性质

• Acid pKa: 1.8803148
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 4.2743464
• LogD (pH = 7.4): 4.2744484
• Log P: 2.2508485
• 摩尔折射率: 125.5131 cm^3
• 极化性: 45.86225 Å^3
• 极化表面积: 58.59 Å^2
• 可自由旋转的化学键: 20
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: >2 mg/mL
• 外观: white to off-white powder

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 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): 3
• 危险公开号: 22-43
• 安全公开号: 36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H317
• GHS警示性声明: P280
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 简要说明: zwitterionic
• Empirical Formula (Hill Notation): C21H46NO4P · xH2O

详细说明

Sigma Aldrich - M9198

Biochem/physiol Actions
Miltefosine induces apoptosis of triple-negative (TN) breast cancer cells by activation of p38 MAPK pathway and differential down regulation of Akt signaling. Miltefosine is an effective anti-tumor treatment of cutaneous lymphoma, cutaneous metastatic melanoma, squamous cell carcinoma, and cutaneous metastases of breast cancer. It also shows remarkable effectiveness against visceral leishmaniasis.1 Both the anti-tumor and the antiprotozoal activities appear to be exerted first by insertion of the molecule into the plasma membrane where it interferes with phospholipid metabolism.
Miltefosine or HePC induces death of triple-negative (TN) breast cancer cells. Miltefosine exerts various modes of action leading to different cell death processes, i.e. apoptosis or non-apoptosis, depending on TN breast cancer cell types. These processes involve the activation of p38 MAPK pathway and differential down regulation of Akt signaling. Miltefosine has been used for breast cancer skin metastases, and is an efficient topical anti-tumoral treatment in patients with cutaneous lymphoma, cutaneous metastases of melanoma and squamous cell carcinoma.