All Photos(1)
Synonym(s):
Choline hexadecyl phosphate, HePC, Hexadecyl phosphocholine, Impavido, Miltex
Empirical Formula (Hill Notation):
C21H46NO4P · xH2O
CAS Number:
Molecular Weight:
407.57 (anhydrous basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.25
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description
zwitterionic
Quality Level
Assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to off-white
solubility
H2O: >2 mg/mL
storage temp.
2-8°C
SMILES string
O.CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C
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
InChI key
NTMJUKLGQGDYOT-UHFFFAOYSA-N
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 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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Skin Sens. 1
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Anita Wnętrzak et al.
The Journal of membrane biology, 246(6), 453-466 (2013-05-16)
Alkylphosphocholines (APCs) belong to a class of synthetic antitumor lipids, which are new-generation anticancer agents. In contrast to traditional antitumor drugs, they do not attack the cell nucleus but, rather, the cellular membrane; however, their mechanism of action is not
Human Choline Kinase-alpha Promotes Hepatitis C Virus RNA Replication through Modulating Membranous Viral Replication Complex Formation
Wong MT and Chen SS
Journal of Virology, JVI-00960 (2016)
Mahshid Mohammadi Bassir et al.
Journal of conservative dentistry : JCD, 16(5), 413-417 (2013-10-02)
Endodontic treatment generally reduces the fracture resistance of teeth. The purpose of this study was to evaluate the fracture resistance and the mode of fracture of endodontically treated human premolars with different amounts of remaining tooth structure. Seventy non-carious human
Heather S Kennedy et al.
Journal of histotechnology, 36(3), 86-91 (2013-09-17)
For researchers seeking to collect spinal cord samples from mice and rats while avoiding acid decalcification, few options are available. Laminectomy is the standard method which yields high quality samples, yet is time consuming and technically difficult. Ejection of the
P Vacchina et al.
Parasites & vectors, 9(1), 621-621 (2016-12-03)
Protozoan parasites of the genus Leishmania are responsible for leishmaniasis, a neglected tropical disease affecting millions worldwide. Visceral leishmaniasis (VL), caused by Leishmania donovani, is the most severe form of leishmaniasis with high rates of mortality if left untreated. Current
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