Skip to Content
Merck

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C21H46NO4P
CAS Number:
58066-85-6
Molecular Weight:
407.57
UNSPSC Code:
12352200
MDL number:
MFCD00133396

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

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.

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

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

Quality Level

100

Biochem/physiol Actions

Cell permeable: no
Primary Target
CTP:phosphocholine cytidyltransferase
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Harmful (C)

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.

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.

Packaging

Packaged under inert gas

Preparation Note

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.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service