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Substance Name: Miltefosine [INN:BAN]
RN: 58066-85-6
UNII: 53EY29W7EC
InChIKey: PQLXHQMOHUQAKB-UHFFFAOYSA-N

Notes

  • CDC: Miltefosine has shown ameba-killing activity against free-living amebae, including Naegleria fowleri, in the laboratory. Miltefosine has also been used to successfully treat patients infected with Balamuthia and disseminated Acanthamoeba infection.

    NCI: An orally- and topically-active alkyl-phosphocholine compound with potential antineoplastic activity. Miltefosine targets cellular membranes, modulating cell membrane permeability, membrane lipid composition, phospholipid metabolism, and mitogenic signal transduction, resulting in cell differentiation and inhibition of cell growth. This agent also inhibits the anti-apoptotic mitogen-activated protein kinase (MAPK) pathway and modulates the balance between the MAPK and pro-apoptotic stress-activated protein kinase (SAPK/JNK) pathways, thereby inducing apoptosis. As an immunomodulator, miltefosine stimulates T-cells, macrophages and the expression of interleukin 3 (IL-3), granulocyte-macrophage colony stimulating factor (GM-CSF), and interferon gamma (INF-gamma).
  • Hexadecyl phosphocholine derivative of cisplatin; did not substantially activate HIV long terminal repeat; less toxic than cisplatin.

Molecular Formula

  • C21-H46-N-O4-P

Molecular Weight

  • 407.5714
 

Classification Codes

  • Anti-Infective Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent

Names and Synonyms

Name of Substance

  • Miltefosine
  • Miltefosine [INN:BAN]

Synonyms

  • 2-(((Hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium hydroxide, inner salt
  • 4-04-00-01460 (Beilstein Handbook Reference)
  • BRN 3690495
  • Choline phosphate, hexadecyl ester, hydroxide, inner salt (6CI)
  • D 18506
  • D-18506
  • Fos-choline 16
  • HDPC
  • Hexadecylphosphocholine
  • Hexadecylphosphorylcholine
  • HPC
  • Impavido
  • Miltefos
  • Miltefosina
  • Miltefosina [INN-Spanish]
  • Miltefosine
  • Miltefosinum
  • Miltefosinum [INN-Latin]
  • Miltex
  • n-Hexadecylphosphocholine
  • n-Hexadecylphosphorylcholine
  • NSC 605583
  • UNII-53EY29W7EC

Systematic Names

  • Choline hydroxide, hexadecyl hydrogen phosphate, inner salt
  • Ethanaminium, 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethyl-, hydroxide, inner salt

Registry Numbers

CAS Registry Number

  • 58066-85-6

FDA UNII

  • 53EY29W7EC

Other Registry Number

  • 93597-88-7

System Generated Number

  • 0058066856

Structure Descriptors

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

InChIKey

PQLXHQMOHUQAKB-UHFFFAOYSA-N

Smiles

CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 246mg/kg (246mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Lipids. Vol. 22, Pg. 930, 1987.