An inhibitor of CCT
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Labeled Version(s)
34707Miltefosine-d4
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Miltefosine

Item No. 63280

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium, inner salt
CAS Number
58066-85-6
Synonyms
  • Hexadecylphosphocholine
  • HPC
  • NSC 605583
Molecular Formula
C21H46NO4P
Formula Weight
407.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: <0.05 mg/mlDMSO: >0.8 mg/mlEthanol: >1.25 mg/mlPBS pH 7.2: >2.5 mg/ml
SMILES
CCCCCCCCCCCCCCCCOP(OCC[N+](C)(C)C)([O-])=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $36

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    100 mg

    $55

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    500 mg

    $135

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    1 g

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    Product Description

    Miltefosine is an inhibitor of CTP:phosphocholine cytidylyltransferase (CCT).1 It inhibits liposome-induced CCT activity in MDCK cell homogenates when used at concentrations ranging from 10 to 50 µM, as well as induces translocation of CCT from the cell membrane to the cytosol in MDCK cells. Miltefosine inhibits phosphatidylcholine biosynthesis induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in MDCK and HeLa cells when used at a concentration of 50 µM.2 It inhibits phosphatidylserine-activated PKC (IC50 = 62 µM), as well as PMA-induced morphological changes and proliferation of MDCK cells.3 Miltefosine is active against clinical isolate promastigotes of L. infantum (EC50s = 5-25 µM).4 Topical application of miltefosine (0.5%) completely eradicates L. amazonensis and induces re-epithelialization of lesions in a mouse model of cutaneous leishmaniasis.5 Formulations containing miltefosine have been used in the treatment of leishmaniasis and various free-living amoeba infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Geilen, C.C., Wieder, T., and Reutter, W. Hexadecylphosphocholine inhibits translocation of CTP: Choline-phosphate cytidylyltransferase in Madin-Darby canine kidney cells. The Journal of Biological Chemisty 267(10), 6719-6724 (1992).

    2. Wieder, T., Geilen, C.C., and Reutter, W. Antagonism of phorbol-ester-stimulated phosphatidylcholine biosynthesis by the phospholipid analogue hexadecylphosphocholine. Biochem. J. 291(Pt. 2), 561-567 (1993).

    3. Geilen, C.C., Haase, R., Buchner, K., et al. The phospholipid analogue, hexadecylphosphocholine, inhibits protein kinase C in vitro and antagonises phorbol ester-stimulated cell proliferation. Eur. J. Cancer 27(12), 1650-1653 (1991).

    4. Espada, C.R., de Castro Levatti, E.V., Boité, M.C., et al. In vitro susceptibility to miltefosine of Leishmania infantum (syn. L. chagasi) isolates from different geographical areas in Brazil. Microorganisms 9(6), 1228 (2021).

    5. Peralta, M.F., Usseglio, N.A., Bracamonte, M.E., et al. Efficacy of topical Miltefosine formulations in an experimental model of cutaneous leishmaniasis. Drug Deliv. Transl. Res. 12(1), 180-196 (2022).

    Product Citations

    von Krusenstiern, A.N., Robson, R.N., Qian, N., et al. Identification of essential sites of lipid peroxidation in ferroptosis. Nat. Chem. Biol. 19(6), 719-730 (2023).

    Gonzalez-Fajardo, L., Fernández, O.L., McMahon-Pratt, D., et al. Ex vivo host and parasite response to antileishmanial drugs and immunomodulators. PLoS Negl. Trop. Dis. 9(5), e0003820 (2015).