M9198
Miltefosine hydrate
≥98% (HPLC)
Synonym(s):
Choline hexadecyl phosphate, HePC, Hexadecyl phosphocholine, Impavido, Miltex
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About This Item
Empirical Formula (Hill Notation):
C21H46NO4P · xH2O
CAS Number:
Molecular Weight:
407.57 (anhydrous basis)
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Product Name
Miltefosine hydrate, ≥98% (HPLC)
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
SMILES string
O.CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C
InChI key
NTMJUKLGQGDYOT-UHFFFAOYSA-N
description
zwitterionic
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to off-white
solubility
H2O: >2 mg/mL
storage temp.
2-8°C
Quality Level
Application
Miltefosine hydrate has been used in the assay for screening compounds targeting n-myristoylation in intracellular Leishmania amastigotes. It has also been used to study its effect on phosphatidylcholine level in the Hepatitis C virus-infected cells.
Miltefosine, a bioactive alkylphospholipd, may be used to study its pharmacokinetics, metabolism, safety, efficacy and delivery formulation as a potential therapeutic for use in cancer treatments such as cutaneous lymphoma, cutaneous metastatic melanoma, squamous cell carcinoma, and cutaneous metastases of breast cancer. It may also be used to study its mechanism of action and value as an anti-leishmaniasis (antiprotozoan) drug. Miltefosine may be used to study its effect on cell signaling pathways that involve processes such as p38 MAPK pathway activation and differential down regulation of Akt signaling.
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. 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 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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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