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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Miltefosine

Cayman Chemical Item Number 63280

HePC (CAS 58066-85-6)

Miltefosine (CAS 58066-85-6)

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Description

Miltefosine is an inhibitor of CTP:phosphocholine cytidylyl transferase and has antimetastatic properties.1,2,3 At concentrations of 3 and 25 µM, miltefosine inhibits proliferation of HaCaT cells (immortalized human keratinocyte cell line) by 50% and 94%, respectively.4 The mechanism of action of miltefosine is not well established, but the antiproliferative effect may be mediated by an increase in cellular ceramide which results in apoptosis. Treatment of cells with 25 µM miltefosine results in a 53% increase in ceramide concentration relative to control.4 Miltefosine is more than 90% effective in eradicating visceral infections of Leishmania species (kala azar), although the mechanism of this antiprotozoal activity is also poorly understood.5

1 Geilen, C.C., Wieder, T., and Reutter, W. Hexadecylphosphocholine inhibits translocation of CTP: Choline-phosphate cytidylyltransferase in Madin-Darby canine kidney cells. J Biol Chem 267 6719-6724 (1992).

2 Wieder, T., Geilen, C.C., and Reutter, W. Antagonism of phorbol-ester-stimulated phosphatidylcholine biosynthesis by the phospholipid analogue hexadecylphosphocholine. Biochem J 291 561-567 (1993).

3 Geilen, C.C., Haase, R., Buchner, K., et al. The phospholipid analogue, hexadecylphosphocholine, inhibits protein kinase C in vitro and antagonises phorbol ester-stimulated cell proliferation. Eur J Cancer 27 1650-1653 (1991).

4 Wieder, T., Orfanos, C.E., and Geilen, C.C. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J Biol Chem 273 11025-11031 (1998).

5 Sundar, S., Jha, T.K., Thakur, C.P., et al. Oral miltefosine for indian visceral leishmaniasis. N Engl J Med 347 (22) 1739-1746 (2002).

Synonyms
  • HePC
Formal Name 1-​hexadecylphosphorylcholine
CAS Number 58066-85-6
Molecular Formula C21H46NO4P
Formula Weight 407.6
Formulation A crystalline solid
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCCCCCCCCCCCCCOP(=O)​(O)​OCC[N]​(C)​(C)​C

Background Reading

Geilen, C.C., Haase, R., Buchner, K., et al. The phospholipid analogue, hexadecylphosphocholine, inhibits protein kinase C in vitro and antagonises phorbol ester-stimulated cell proliferation. Eur J Cancer 27 1650-1653 (1991).

Wieder, T., Orfanos, C.E., and Geilen, C.C. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J Biol Chem 273 11025-11031 (1998).

Wieder, T., Geilen, C.C., and Reutter, W. Antagonism of phorbol-ester-stimulated phosphatidylcholine biosynthesis by the phospholipid analogue hexadecylphosphocholine. Biochem J 291 561-567 (1993).

Geilen, C.C., Wieder, T., and Reutter, W. Hexadecylphosphocholine inhibits translocation of CTP: Choline-phosphate cytidylyltransferase in Madin-Darby canine kidney cells. J Biol Chem 267 6719-6724 (1992).

Sundar, S., Jha, T.K., Thakur, C.P., et al. Oral miltefosine for indian visceral leishmaniasis. N Engl J Med 347 (22) 1739-1746 (2002).

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Miltefosine is available in the following screening library:

Size Price Quantity Subtotal
25 mg $12.00 $0.00
50 mg $23.00 $0.00
100 mg $43.00 $0.00
500 mg $192.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-02-11. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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