Miltefosine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 201890

CAS#: 58066-85-6

Description: Miltefosine is an orally- and topically-active alkyl-phosphocholine compound with potential antineoplastic activity. Miltefosine targets cellular membranes, modulating cell membrane permeability, membrane lipid composition, phospholipid metabolism, and mitogenic signal transduction, resulting in cell differentiation and inhibition of cell growth. This agent also inhibits the anti-apoptotic mitogen-activated protein kinase (MAPK) pathway and modulates the balance between the MAPK and pro-apoptotic stress-activated protein kinase (SAPK/JNK) pathways, thereby inducing apoptosis. As an immunomodulator, miltefosine stimulates T-cells, macrophages and the expression of interleukin 3 (IL-3), granulocyte-macrophage colony stimulating factor (GM-CSF), and interferon gamma (INF-gamma). Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

Size
Price

100mg
USD 200
Size
Price

1g
USD 460
Size
Price

Miltefosine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 201890
Name: Miltefosine
CAS#: 58066-85-6
Chemical Formula: C21H46NO4P
Exact Mass: 407.31645
Molecular Weight: 407.57
Elemental Analysis: C, 61.89; H, 11.38; N, 3.44; O, 15.70; P, 7.60


Synonym: Miltefosin CHePCHexadecylphosphocholineHDPCHexadecylphosphorylcholineMiltefosinum; mpavido; Miltex; Choline Phosphate Hexadecyl Ester Hydroxide Inner Salt; hexadecylphosphocholine; Miltefosin; Miltefosina; Miltefosinum;

IUPAC/Chemical Name: hexadecyl (2-(trimethylammonio)ethyl) phosphate

InChi Key: PQLXHQMOHUQAKB-UHFFFAOYSA-N

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

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


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Miltefosine (INN, trade names Impavido and Miltex) is a phospholipid drug. Chemically it is a derivative of alkylphosphocholine compounds discovered in the early 1980s. It was developed in the late 1980s as an anticancer drug by German scientists Hansjörg Eibl and Clemens Unger. Simultaneously but independently it was found that the drug could kill Leishmania parasites, and since the mid-1990s successful clinical trials were conducted. The drug became the first (and still the only prescribed) oral drug in the treatment of leishmaniasis. It is now known to be a broad-spectrum antimicrobial drug, active against pathogenic bacteria and fungi, as well as human trematode Schistosoma mansoni and its vector host, the snail Biomphalaria alexandrina. It can be administered orally and topically. In the target cell, it acts as an Akt inhibitor. Therefore, it is also under investigation as a potential therapy against HIV infection (http://en.wikipedia.org/wiki/Miltefosine)
  
 
 


References

1: Ordaz-Farias A, Muñoz-Garza FZ, Sevilla-Gonzalez FK, Arana-Guajardo A, Ocampo-Candiani J, Treviño-Garza N, Becker I, Camacho-Ortiz A. Transient Success Using Prolonged Treatment with Miltefosine for a Patient with Diffuse Cutaneous Leishmaniasis Infected with Leishmania mexicana mexicana. Am J Trop Med Hyg. 2013 Jan;88(1):153-6. doi: 10.4269/ajtmh.2012.11-0592. Epub 2012 Dec 12. PubMed PMID: 23243111.

2: Kulshrestha A, Bhandari V, Mukhopadhyay R, Ramesh V, Sundar S, Maes L, Dujardin JC, Roy S, Salotra P. Validation of a simple resazurin-based promastigote assay for the routine monitoring of miltefosine susceptibility in clinical isolates of Leishmania donovani. Parasitol Res. 2013 Feb;112(2):825-8. doi: 10.1007/s00436-012-3212-3. Epub 2012 Dec 13. PubMed PMID: 23239091.

3: Uranw S, Ostyn B, Dorlo TP, Hasker E, Dujardin B, Dujardin JC, Rijal S, Boelaert M. Adherence to miltefosine treatment for visceral leishmaniasis under routine conditions in Nepal. Trop Med Int Health. 2013 Feb;18(2):179-87. doi: 10.1111/tmi.12025. Epub 2012 Nov 30. PubMed PMID: 23199340.

4: Wiederhold NP, Najvar LK, Bocanegra R, Kirkpatrick WR, Sorrell TC, Patterson TF. Limited activity of miltefosine in murine models of cryptococcal meningoencephalitis and disseminated cryptococcosis. Antimicrob Agents Chemother. 2013 Feb;57(2):745-50. doi: 10.1128/AAC.01624-12. Epub 2012 Nov 19. PubMed PMID: 23165465.

5: Sundar S, Sinha P, Jha TK, Chakravarty J, Rai M, Kumar N, Pandey K, Narain MK, Verma N, Das VN, Das P, Berman J, Arana B. Oral miltefosine for Indian post-kala-azar dermal leishmaniasis: a randomised trial. Trop Med Int Health. 2013 Jan;18(1):96-100. doi: 10.1111/tmi.12015. Epub 2012 Nov 8. PubMed PMID: 23136856.

6: López C, Sanna E, Carreras L, Vega M, Rotger C, Costa A. Molecular recognition of zwitterions: enhanced binding and selective recognition of miltefosine by a squaramide-based host. Chem Asian J. 2013 Jan;8(1):84-7. doi: 10.1002/asia.201200881. Epub 2012 Nov 5. PubMed PMID: 23129548.

7: Patra P, Guha SK, Maji AK, Saha P, Ganguly S, Chakraborty A, Kundu PK, Sarker S, Ray K. Efficacy of oral miltefosine in visceral leishmaniasis in rural West Bengal, India. Indian J Pharmacol. 2012 Jul-Aug;44(4):500-3. doi: 10.4103/0253-7613.99326. PubMed PMID: 23087513; PubMed Central PMCID: PMC3469955.

8: Thakur A, Joshi N, Shanmugam T, Banerjee R. Proapoptotic miltefosine nanovesicles show synergism with paclitaxel: Implications for glioblastoma multiforme therapy. Cancer Lett. 2012 Aug 27. doi:pii: S0304-3835(12)00510-1. 10.1016/j.canlet.2012.08.022. [Epub ahead of print] PubMed PMID: 22935677.

9: Magerl M, Rother M, Bieber T, Biedermann T, Brasch J, Dominicus R, Hunzelmann N, Jakob T, Mahler V, Popp G, Schäkel K, Schlingensiepen R, Schmitt J, Siebenhaar F, Simon JC, Staubach P, Wedi B, Weidner C, Maurer M. Randomized, double-blind, placebo-controlled study of safety and efficacy of miltefosine in antihistamine-resistant chronic spontaneous urticaria. J Eur Acad Dermatol Venereol. 2012 Aug 29. doi: 10.1111/j.1468-3083.2012.04689.x. [Epub ahead of print] PubMed PMID: 22928719.

10: Weingärtner A, Kemmer G, Müller FD, Zampieri RA, Gonzaga dos Santos M, Schiller J, Pomorski TG. Leishmania promastigotes lack phosphatidylserine but bind annexin V upon permeabilization or miltefosine treatment. PLoS One. 2012;7(8):e42070. doi: 10.1371/journal.pone.0042070. Epub 2012 Aug 1. PubMed PMID: 22870283; PubMed Central PMCID: PMC3411662.