Miltefosine

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)[1]
  • US: ℞-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[2]
ExcretionPrimarily fecal
Identifiers
IUPAC name
  • 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)
SMILES
  • [O-]P(=O)(OCCCCCCCCCCCCCCCC)OCC[N+](C)(C)C
InChI
  • 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)

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.[3] This includes the three forms of leishmaniasis: cutaneous, visceral and mucosal.[4] It may be used with liposomal amphotericin B or paromomycin.[5] It is taken by mouth.[4]

Common side effects include vomiting, abdominal pain, fever, headaches, and decreased kidney function.[3] More severe side effects may include Stevens–Johnson syndrome or low blood platelets.[3] Use during pregnancy appears to cause harm to the baby and use during breastfeeding is not recommended.[3] How it works is not entirely clear.[3]

Miltefosine was first made in the early 1980s and studied as a treatment for cancer.[6] A few years later it was found to be useful for leishmaniasis and was approved for this use in 2002 in India.[7] It is on the World Health Organization's List of Essential Medicines.[8][9]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Cite error: The named reference dorlo was invoked but never defined (see the help page).
  3. ^ a b c d e American Society of Health-System Pharmacists (26 February 2016). "Miltefosine Monograph for Professionals". www.drugs.com. Archived from the original on 17 November 2016. Retrieved 16 November 2016.
  4. ^ a b "FDA approves Impavido to treat tropical disease leishmaniasis". U.S. Food and Drug Administration (FDA) (Press release). 19 March 2014. Archived from the original on 3 September 2014. Retrieved 30 August 2014.
  5. ^ Cite error: The named reference WHO2010 was invoked but never defined (see the help page).
  6. ^ Greenwood D (2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. p. 310. ISBN 978-0-19-953484-5. Archived from the original on 2017-09-10.
  7. ^ Kumar A (2013). Leishmania and Leishmaniasis. Springer Science & Business Media. p. 39. ISBN 978-1-4614-8869-9. Archived from the original on 2017-09-10.
  8. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
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