CAS No 58066-85-6 , hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

Title: Miltefosine
CAS Registry Number: 58066-85-6
CAS Name: 2-[[(Hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium inner salt
Synonyms: choline phosphate hexadecyl ester, hydroxide, inner salt; hexadecyl 2-(N,N,N-trimethylamino)ethyl phosphate; n-hexadecylphosphorylcholine; hexadecylphosphocholine; HPC
Manufacturers' Codes: D-18506
Trademarks: Impavido (Zentaris); Miltex (Baxter)
Molecular Formula: C21H46NO4P
Molecular Weight: 407.57
Percent Composition: C 61.89%, H 11.38%, N 3.44%, O 15.70%, P 7.60%
Literature 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).
Properties: mp 232-234° (dec); discoloration at 225°. LD50 in rats (mg/kg): 246 orally (Muschiol).
Melting point: mp 232-234° (dec)
Toxicity data: LD50 in rats (mg/kg): 246 orally (Muschiol)
Therap-Cat: Antineoplastic; antiprotozoal (Leishmania).
Keywords: Antineoplastic; Antiprotozoal (Leishmania).