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Key Documents

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M5571

Sigma-Aldrich

Miltefosine

≥98% (perchloric acid titration)

Sinónimos:

Choline hexadecyl phosphate, HePC, Hexadecyl phosphocholine

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About This Item

Fórmula empírica (notación de Hill):
C21H46NO4P
Número de CAS:
58066-85-6
Peso molecular:
407.57
MDL number:
MFCD00133396
UNSPSC Code:
51191904
PubChem Substance ID:
329818017
NACRES:
NA.85

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

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Categorías relacionadas

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

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_germany

WGK 3

ppe

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

Certificados de análisis (COA)

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Suresh K Tipparaju et al.
Journal of medicinal chemistry, 51(23), 7344-7347 (2008-11-08)
The first synthesis and biological evaluation of antibiotic 31 (A-33853) and its analogues are reported. Initial screening for inhibition of L. donovani, T. b. rhodesiense, T. cruzi, and P. falciparum cultures followed by determination of IC(50) in L. donovani and
Maria V Papadopoulou et al.
Journal of medicinal chemistry, 54(23), 8214-8223 (2011-10-26)
A series of novel 2-nitro-1H-imidazole- and 3-nitro-1H-1,2,4-triazole-based aromatic and aliphatic amines were screened for antitrypanosomal activity and mammalian cytotoxicity by the Drugs for Neglected Diseases initiative (DNDi). Out of 42 compounds tested, 18 3-nitro-1,2,4-triazoles and one 2-nitroimidazole displayed significant growth
Abdullah Alotaibi et al.
Scientific reports, 9(1), 11364-11364 (2019-08-08)
Extracts of 35 samples of European propolis were tested against wild type and resistant strains of the protozoal pathogens Trypanosoma brucei, Trypanosoma congolense and Leishmania mexicana. The extracts were also tested against Crithidia fasciculata a close relative of Crithidia mellificae
Nathan P Wiederhold et al.
Antimicrobial agents and chemotherapy, 57(2), 745-750 (2012-11-21)
Miltefosine is an alkyl phosphocholine with good oral bioavailability and in vitro activity against Cryptococcus species that has gained interest as an additional agent for cryptococcal infections. Our objective was to further evaluate the in vivo efficacy of miltefosine in
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.
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