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Merck
CN

850337P

Avanti

MAPCHO™-16

Avanti Research™ - A Croda Brand

Synonym(s):

HPC; Fos-Choline-16; FOS16; FC-16; Miltefosine

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About This Item

Empirical Formula (Hill Notation):
C21H46NO4P
CAS Number:
58066-85-6
Molecular Weight:
407.57
MDL number:
MFCD00133396
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

MAPCHO™-16, n-hexadecylphosphocholine, powder

SMILES string

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

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

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 g (850337P-1g)
pkg of 1 × 5 g (850337P-5g)

manufacturer/tradename

Avanti Research™ - A Croda Brand 850337P

shipped in

dry ice

storage temp.

−20°C

Packaging

20 mL Clear Glass Screw Cap Vial (850337P-1g)
60 mL Amber Wide Mouth Glass Bottle with Screw Cap (850337P-5g)

Application

MAPCHO™-16 has been used to test against Leishmania intracellular amastigotes. It has also been use to evaluate its efficacy in L. infantum chagasi infections.

Biochem/physiol Actions

MAPCHO™-16/ n-hexadecylphosphocholine/Miltefosine can be used as a stationary phase to determine total acidity of divalent cations by ion chromatography. It is used in the oral treatment of human leishmaniasis 

General description

Hexadecylphosphocholine is a structural analog of palmitoyl lysophosphatidylcholine that is more stable to hydrolytic degradation. The lipid is often used as a detergent for membrane protein solubilization and purification. It has been shown to have antineoplastic and antiprotozoal activity.

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC
MAPCHO is a trademark of Avanti Polar Lipids, LLC

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

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Combination therapy with nitazoxanide and amphotericin B, Glucantime, miltefosine and sitamaquine against Leishmania (Leishmania) infantum intracellular amastigotes
Mesquita JT, et al.
Acta Tropica, 130, 112-116 (2014)
Synthesis of 16-mercaptohexadecylphosphocholine, a miltefosine analog with leishmanicidal activity
Hornillos V, et al.
Bioorganic & medicinal chemistry letters, 16(19), 5190-5193 (2006)
Determination of total acidity and of divalent cations by ion chromatography with n-hexadecylphosphocholine as the stationary phase
Hu W, et al.
Journal of Chromatography A, 956(1-2), 139-145 (2002)
Juliana Q Reimão et al.
PLoS neglected tropical diseases, 9(2), e0003556-e0003556 (2015-02-14)
The only oral drug available for the treatment of leishmaniasis is miltefosine, described and approved for visceral leishmaniasis in India. Miltefosine is under evaluation for the treatment of cutaneous leishmaniasis in the Americas although its efficacy for the treatment of
Bruno M Castro et al.
The journal of physical chemistry. B, 117(26), 7929-7940 (2013-06-07)
Edelfosine (1-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine) and miltefosine (hexadecylphosphocholine) are synthetic alkylphospholipids (ALPs) that are reported to selectively accumulate in tumor cell membranes, inducing Fas clustering and activation on lipid rafts, triggering apoptosis. However, the exact mechanism by which these lipids elicit these events

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