An internal standard for the quantification of miltefosine
Related Products
Unlabeled Version(s)
63280Miltefosine
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Miltefosine-d4

Item No. 34707

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium-1,1,2,2-d4, inner salt
Synonyms
  • Hexadecylphosphocholine-d4
  • HPC-d4
Molecular Formula
C21H42D4NO4P
Formula Weight
411.6
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: solubleWater: soluble
SMILES
CCCCCCCCCCCCCCCCOP(OC([2H])([2H])C([2H])([2H])[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/i19D2,21D2
InChi Key
PQLXHQMOHUQAKB-KQHQIZQISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $86

    Add

    5 mg

    $406

    Add

    10 mg

    $725

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Miltefosine-d4 is intended for use as an internal standard for the quantification of miltefosine (Item No. 63280) by GC- or LC-MS. 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).