hydrate hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

• ChemBase ID: 154522
• Molecular Formular: C21H48NO5P
• Molecular Mass: 425.583281
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: hydrate hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
• IUPAC Traditional name: hydrate miltex
• Synonyms: Choline hexadecyl phosphate; HePC; Hexadecyl phosphocholine; Impavido; Miltex; Miltefosine hydrate

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 1.8803148
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.2743464
• LogD (pH = 7.4): 4.2744484
• Log P: 2.2508485
• Molar Refractivity: 125.5131 cm^3
• Polarizability: 45.86225 Å^3
• Polar Surface Area: 58.59 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P280
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Description: zwitterionic
• Empirical Formula (Hill Notation): C21H46NO4P · xH2O

DETAILS

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.