Miltefosine


Miltefosine
Systematic (IUPAC) name
2-(hexadecoxy-oxido-phosphoryl)oxyethyl-trimethyl-azanium
Identifiers
CAS number	58066-85-6
ATC code	L01 XX09
PubChem	3599
Chemical data
Formula	C₂₁H₄₆N O₄P
Mol. weight	407.568 g/mol
Pharmacokinetic data
Bioavailability	High
Metabolism	?
Half life	6 to 8 days
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	Oral

Miltefosine (INN, trade names Impavido® and Miltex®) is an antiprotozoal drug. Originally developed as an antineoplastic, it is now registered and used by Zentaris GmbH in India, Colombia and Germany for the treatment of visceral and cutaneous leishmaniasis, and is undergoing clinical trials for this use in several other countries, such as Brazil^[1] and Guatemala.^[2] It is currently the only effective oral treatment for leishmaniasis.

Recent animal studies suggest miltefosine may also be effective against Trypanosoma cruzi, the parasite responsible for Chagas' disease,^[3] and several pathogenic fungi, including Cryptococcus neoformans, Candida, Aspergillus and Fusarium.^[4]

Hexadecyltrimethylammonium bromide, a compound structurally similar to miltefosine, was recently found to exhibit potent in vitro activity against Plasmodium falciparum.^[5]

[edit] Side effects

The main side effects reported with miltefosine treatment are nausea and vomiting. Miltefosine has exhibited teratogenicity, and should not be administered to pregnant women.

^ Cristina, Márcia, Pedrosa, Robert. "Hospital de Doenças Tropicais testa droga contra calazar", Sapiência, Fundação de Amparo à Pesquisa do Estado do Piauí, September 2005. Retrieved on 2006-09-01. (in Portuguese)
^ Soto J, Berman J (2006). "Treatment of New World cutaneous leishmaniasis with miltefosine.". Trans R Soc Trop Med Hyg. PMID 16930649.
^ Saraiva V, Gibaldi D, Previato J, Mendonça-Previato L, Bozza M, Freire-De-Lima C, Heise N (2002). "Proinflammatory and cytotoxic effects of hexadecylphosphocholine (miltefosine) against drug-resistant strains of Trypanosoma cruzi.". Antimicrob Agents Chemother 46 (11): 3472-7. PMID 12384352.
^ Widmer F, Wright L, Obando D, Handke R, Ganendren R, Ellis D, Sorrell T (2006). "Hexadecylphosphocholine (miltefosine) has broad-spectrum fungicidal activity and is efficacious in a mouse model of cryptococcosis.". Antimicrob Agents Chemother 50 (2): 414-21. PMID 16436691.
^ Choubey V, Maity P, Guha M, Kumar S, Shrivastava K, Puri SK, Bandyopadhyay U (2006). "Inhibition of Plasmodium falciparum choline kinase by hexadecyltrimethylammonium bromide: A possible antimalarial mechanism of hexadecyltrimethylammonium bromide.". Antimicrob Agents Chemother. PMID 17145794.