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M5571

Sigma-Aldrich

Miltefosine

≥98% (perchloric acid titration)

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Synonym(s):
Choline hexadecyl phosphate, HePC, Hexadecyl phosphocholine
Empirical Formula (Hill Notation):
C21H46NO4P
CAS Number:
Molecular Weight:
407.57
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

synthetic (organic)

Quality Level

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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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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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
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
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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