6198. Miltefosine

Nomenclature

CAS number: 58066-85-6
2-[[(Hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium inner salt; choline phosphate hexadecyl ester, hydroxide, inner salt; hexadecyl 2-(N,N,N-trimethylamino)ethyl phosphate; n-hexadecylphosphorylcholine; hexadecylphosphocholine; HPC; D-18506; Impavido (Zentaris); Miltex (Baxter).
C21H46NO4P; mol wt 407.57.
C 61.89%, H 11.38%, N 3.44%, O 15.70%, P 7.60%.

Description and references

Synthetic phospholipid; affects cell-signaling pathways and membrane synthesis. Synthesis: U. Kaatze et al., Chem. Phys. Lipids 27, 263 (1980); W. J. Hansen et al., Lipids 17, 453 (1982). See also: H. Eibl, EP 225608; idem, US 4837023 (1987, 1989 both to Max-Planck Ges. Wissensch.). Toxicity and anticancer properties: C. Muschiol et al., Lipids 22, 930 (1987). Structure-activity study: M. R. Berger et al., Cancer Treat. Rev. 17, 143 (1990). HPTLC determn in plasma: I. Rustenbeck, S. Lenzen, J. Chromatogr. 525, 85 (1990). Clinical evaluation in topical treatment of cutaneous breast cancer metastases: C. Unger et al., Cancer Treat. Rev. 17, 243 (1990). Clinical trial in visceral leishmaniasis: S. Sundar et al., N. Engl. J. Med. 347, 1739 (2002). Review: H. Eibl, C. Unger, Cancer Treat. Rev. 17, 233-242 (1990).

Chemical structure

Properties

mp 232-234° (dec); discoloration at 225°. LD50 in rats (mg/kg): 246 orally (Muschiol).

Therapeutic Category

Antineoplastic; antiprotozoal (Leishmania).

Keywords

Antineoplastic; Antiprotozoal (Leishmania)