Miltefosine

Miltefosine, sold under the trade name Impavido among others, is a medication mainly used to treat leishmaniasis and free-living amoeba infections such as Naegleria fowleri and Balamuthia mandrillaris. This includes the three forms of leishmaniasis: cutaneous, visceral and mucosal. It may be used with liposomal amphotericin B or paromomycin. It is taken by mouth.

Miltefosine
Clinical data
Trade namesImpavido, Miltex, others
AHFS/Drugs.comMonograph
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
  • US: WARNINGRx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityHigh
Protein binding~98%
MetabolismSlow hepatic (non-CYP-dependent)
Elimination half-life6 to 8 days and 31 days
ExcretionPrimarily fecal
Identifiers
  • 2-(hexadecoxy-oxido-phosphoryl)oxyethyl-trimethyl-azanium
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.151.328
Chemical and physical data
FormulaC21H46NO4P
Molar mass407.576 g·mol−1
3D model (JSmol)
Melting point232 to 234 °C (450 to 453 °F)
  • [O-]P(=O)(OCCCCCCCCCCCCCCCC)OCC[N+](C)(C)C
  • 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 Y
  • Key:PQLXHQMOHUQAKB-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Common side effects include vomiting, abdominal pain, fever, headaches, and decreased kidney function. More severe side effects may include Stevens–Johnson syndrome or low blood platelets. Use during pregnancy appears to cause harm to the baby and use during breastfeeding is not recommended. How it works is not entirely clear.

Miltefosine was first made in the early 1980s and studied as a treatment for cancer. A few years later it was found to be useful for leishmaniasis and was approved for this use in 2002 in India. It is on the World Health Organization's List of Essential Medicines.

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