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M5571

Miltefosine

≥98% (perchloric acid titration)

Synonym(s):

Choline hexadecyl phosphate, HePC, Hexadecyl phosphocholine

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About This Item

Empirical Formula (Hill Notation):
C21H46NO4P
CAS Number:
58066-85-6
Molecular Weight:
407.57
NACRES:
NA.85
PubChem Substance ID:
329818017
UNSPSC Code:
51191904
MDL number:
MFCD00133396
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biological source

synthetic (organic)

Quality Level

200

description

zwitterionic

assay

≥98% (perchloric acid titration)

form

powder

solubility

H2O: 10 mg/mL, clear, colorless

functional group

phospholipid

lipid type

phospholipids

storage temp.

room temp

SMILES string

[O-]P(OCC[N+](C)(C)C)(OCCCCCCCCCCCCCCCC)=O

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

Application


  • Easy one-pot synthesis of multifunctionalized indole-pyrrole hybrids as a new class of antileishmanial agents.: This study underlines the necessity for innovative treatments amidst growing resistance to established drugs such as miltefosine which is used as a positive control reference, potentially setting a new direction for antileishmanial drug development (Ciccone et al., 2024).

Biochem/physiol Actions

Inhibitor of protein kinase C and of phosphatidylcholine synthesis. Used for the treatment of visceral and cutaneous leishmaniasis. Active against metronidazole-resistant and -susceptible strains of Trichomonas vaginalis

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Thomas P C Dorlo et al.
Antimicrobial agents and chemotherapy, 52(8), 2855-2860 (2008-06-04)
The pharmacokinetics of miltefosine in leishmaniasis patients are, to a great extent, unknown. We examined and characterized the pharmacokinetics of miltefosine in a group of patients with Old World (Leishmania major) cutaneous leishmaniasis. Miltefosine plasma concentrations were determined in samples
M Rakotomanga et al.
Antimicrobial agents and chemotherapy, 51(4), 1425-1430 (2007-01-24)
Miltefosine (hexadecylphosphocholine [HePC]) is the first orally active antileishmanial drug. Transient HePC treatment of Leishmania donovani promastigotes at 10 microM significantly reduced the phosphatidylcholine content and enhanced the phosphatidylethanolamine (PE) content in parasite membranes, suggesting a partial inactivation of PE-N-methyltransferase.
Thomas P C Dorlo et al.
The Journal of antimicrobial chemotherapy, 67(11), 2576-2597 (2012-07-27)
Miltefosine is an alkylphosphocholine drug with demonstrated activity against various parasite species and cancer cells as well as some pathogenic bacteria and fungi. For 10 years it has been licensed in India for the treatment of visceral leishmaniasis (VL), a
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