475841
Miltefosine
An ether lipid analog that acts as an inhibitor of CTP:phosphocholine cytidyltransferase and displays remarkable antiproliferative effect both in vitro and in vivo.
Synonym(s):
Miltefosine, HePC, 1-Hexadecylphosphorylcholine
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About This Item
Empirical Formula (Hill Notation):
C21H46NO4P
CAS Number:
Molecular Weight:
407.57
MDL number:
UNSPSC Code:
12352200
Recommended Products
Quality Level
assay
≥98% (TLC)
form
crystalline solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
solubility
ethanol: 1 mg/mL
PBS, pH 7.2: 2.5 mg/mL
DMSO: 800 μg/mL
shipped in
ambient
storage temp.
−20°C
InChI
1S/C21H46NO4P/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
InChI key
PQLXHQMOHUQAKB-UHFFFAOYSA-N
General description
An ether lipid analog that acts as an inhibitor of CTP:phosphocholine cytidyltransferase. Reported to exhibit anti-proliferative and anti-metastatic effects in vitro and in vivo. Also reported to induce apoptosis mediated by cell-permeable ceramides. Shown to have anti-protozoal activity against Leishmania species.
Biochem/physiol Actions
Cell permeable: no
Primary Target
CTP:phosphocholine cytidyltransferase
CTP:phosphocholine cytidyltransferase
Product does not compete with ATP.
Reversible: no
Packaging
Packaged under inert gas
Warning
Toxicity: Harmful (C)
Reconstitution
Following reconstitution in ethanol or DMSO, aliquot and freeze (-20°C). Stock solutions in ethanol or DMSO are stable for up to 3 months at -20°C. Stock solutions in PBS are stable for up to 24 h at -20°C.
Other Notes
Wieder, T., et al. 1998. J. Biol. Chem.273, 11025.
Wieder, T., et al. 1993. Biochem. J.291, 561.
Geilen, C.C., et al. 1992. J. Biol. Chem.267, 6719.
Geilen, C.C., et al. 1991. Eur. J. Cancer27, 1650.
Wieder, T., et al. 1993. Biochem. J.291, 561.
Geilen, C.C., et al. 1992. J. Biol. Chem.267, 6719.
Geilen, C.C., et al. 1991. Eur. J. Cancer27, 1650.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk_germany
WGK 3
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T Wieder et al.
The Biochemical journal, 291 ( Pt 2), 561-567 (1993-04-15)
The antagonization of phorbol 12-myristate 13-acetate (PMA)-stimulated phosphatidylcholine (PtdCho) biosynthesis by the phospholipid analogue hexadecylphosphocholine (HePC) in MDCK cells was investigated and compared with the corresponding influence in HeLa cells. In both cell lines, PMA-stimulated PtdCho biosynthesis was antagonized by
C C Geilen et al.
The Journal of biological chemistry, 267(10), 6719-6724 (1992-04-05)
The mechanism of the inhibition of phosphatidylcholine biosynthesis by the phospholipid analogue, hexadecylphosphocholine, was investigated in Madin-Darby canine kidney cells. In the presence of 50 mumol/liter hexadecylphosphocholine, there was a translocation of CTP:choline-phosphate cytidylyltransferase (EC 22.7.7.15) activity from the membranes
Yash Gupta et al.
Journal of food and drug analysis, 30(1), 128-149 (2022-06-02)
Leishmaniasis remains a serious public health problem in many tropical regions of the world. Among neglected tropical diseases, the mortality rate of leishmaniasis is second only to malaria. All currently approved therapeutics have toxic side effects and face rapidly increasing
C C Geilen et al.
European journal of cancer (Oxford, England : 1990), 27(12), 1650-1653 (1991-01-01)
The antineoplastic agent, hexadecylphosphocholine, a phospholipid analogue, inhibited phosphatidylserine-activated protein kinase C in vitro at concentrations higher than 40 mumol/l. The half-inhibitory concentration (IC50) was 62 mumol/l. Another alkylphosphocholine, dodecylphosphocholine, did not have an inhibitory effect on protein kinase C.
T Wieder et al.
The Journal of biological chemistry, 273(18), 11025-11031 (1998-06-06)
The prototype of a new class of antiproliferative phospholipid analogs, hexadecylphosphocholine (HePC), has been shown to inhibit tumor growth and is currently used for the treatment of cutaneous metastases of mammary carcinomas. Although several cellular targets of HePC, e.g. protein
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