Miltefosine

Catalog Number Size Price Stock Quantity
B2693-072166 5 g $299 In stock
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Product Information

Molecular Formula:
C21H46NO4P
Molecular Weight:
407.57
Description
Miltefosine inhibits PI3K/Akt activity with ED50 of 17.2 μM and 8.1 μM in carcinoma cell lines A431 and HeLa, first oral drug for Visceral leishmaniasis, effective against both promastigotes and amastigotes.
Synonyms
n-hexadecylphosphocholine; Hexadecylphosphocholine; Miltex; Impavido; 2-[[(Hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium; MAPCHO®-16; C-16Miltefosine
IUPAC Name
hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
Canonical SMILES
CCCCCCCCCCCCCCCCOP(=O)([O-])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
InChI Key
PQLXHQMOHUQAKB-UHFFFAOYSA-N
Melting Point
223-228°C (dec.)
Flash Point
320 °F
Purity
>98%
Solubility
Soluble in Chloroform (Slightly), Methanol (Slightly)
Appearance
White to Off-white Solid
Application
Antineoplastic Agents
Storage
Store at -20°C
Dissociation Constants
~2

Computed Properties

XLogP3
6.7
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
20
Exact Mass
407.31644595 g/mol
Monoisotopic Mass
407.31644595 g/mol
Topological Polar Surface Area
58.6Ų
Heavy Atom Count
27
Formal Charge
0
Complexity
363
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes

Patents

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Literatures

PMID Publication Date Title Journal
33450054 2021-03-01 The anti-parasitic drug miltefosine suppresses activation of human eosinophils and ameliorates allergic inflammation in mice British journal of pharmacology
32020584 2020-05-01 The IUPHAR Guide to Immunopharmacology: connecting immunology and pharmacology Immunology
31265827 2019-09-01 Dimethylsphingosine and miltefosine induce apoptosis in lung adenocarcinoma A549 cells in a synergistic manner Chemico-biological interactions
27556028 2016-01-01 Screening of Drugs Inhibiting In vitro Oligomerization of Cu/Zn-Superoxide Dismutase with a Mutation Causing Amyotrophic Lateral Sclerosis Frontiers in molecular biosciences
25601455 2015-05-01 Miltefosine for visceral and cutaneous leishmaniasis: drug characteristics and evidence-based treatment recommendations Clinical infectious diseases : an official publication of the Infectious Diseases Society of America
24890590 2014-08-01 Studies on the antileishmanial mechanism of action of the arylimidamide DB766: azole interactions and role of CYP5122A1 Antimicrobial agents and chemotherapy
23968432 2013-09-26 Natural product derived antiprotozoal agents: synthesis, biological evaluation, and structure-activity relationships of novel chromene and chromane derivatives Journal of medicinal chemistry
23891181 2013-09-01 Synthesis and antifungal activities of miltefosine analogs Bioorganic & medicinal chemistry letters
23792315 2013-08-01 Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride European journal of medicinal chemistry
23795673 2013-07-11 Synthesis and antiprotozoal activity of dicationic m-terphenyl and 1,3-dipyridylbenzene derivatives Journal of medicinal chemistry
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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