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Miltefosine

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)

Miltefosine is also an antiprotozoal drug. Originally developed as an antineoplastic, it is finding use as an antiprotozoal drug. It can be administered orally and topically.  Miltefosine is registered and used by Zentaris GmbH in India, Colombia and Germany for the treatment of visceral and cutaneous leishmaniasis, and is undergoing clinical trials for this use in several other countries, such as Brazil and Guatemala.  It is currently the only effective oral treatment for leishmaniasis. Miltefosine is one of the few orally administered drugs that is effective against Leishmania.  Miltefosine is being investigated by researchers interested in finding treatments for infections which have become resistant to existing drugs. Animal and in-vitro studies suggest it may have broad anti-protozoal and anti-fungal properties:

Miltefosine is also under investigation as a potential therapy against HIV infection. Miltefosine targets HIV infected macrophages, which play a role in vivo as long-lived HIV-1 reservoirs. The HIV protein Tat activates pro-survival PI3K/Akt pathway in primary human macrophages. Miltefosine acts by inhibiting the PI3K/Akt pathway, thus removing the infected macrophages from circulation, without affecting healthy cells. see: http://en.wikipedia.org/wiki/Miltefosine.

Current developer:    Aeterna Zentaris, Inc

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21: Tappe D, Müller A, Stich A. Resolution of cutaneous old world and new world leishmaniasis after oral miltefosine treatment. Am J Trop Med Hyg. 2010 Jan;82(1):1-3. PubMed PMID: 20064985; PubMed Central PMCID: PMC2803499.

22: Kumar D, Ramesh V, Verma S, Ramam M, Salotra P. Post-kala-azar dermal leishmaniasis (PKDL) developing after treatment of visceral leishmaniasis with amphotericin B and miltefosine. Ann Trop Med Parasitol. 2009 Dec;103(8):727-30. PubMed PMID: 20030997.

23: Griewank K, Gazeau C, Eichhorn A, von Stebut E. Miltefosine efficiently eliminates Leishmania major amastigotes from infected murine dendritic cells without altering their immune functions. Antimicrob Agents Chemother. 2010 Feb;54(2):652-9. Epub 2009 Dec 7. PubMed PMID: 19995922; PubMed Central PMCID: PMC2812123.

24: van Thiel PP, Leenstra T, Kager PA, de Vries HJ, van Vugt M, van der Meide WF, Bart A, Zeegelaar JE, van der Sluis A, Schallig HD, van Gool T, Faber WR, de Vries PJ. Miltefosine treatment of Leishmania major infection: an observational study involving Dutch military personnel returning from northern Afghanistan. Clin Infect Dis. 2010 Jan 1;50(1):80-3. PubMed PMID: 19951107.

25: Esteves MA, Fragiadaki I, Lopes R, Scoulica E, Cruz ME. Synthesis and biological evaluation of trifluralin analogues as antileishmanial agents. Bioorg Med Chem. 2010 Jan 1;18(1):274-81. Epub 2009 Oct 31. PubMed PMID: 19926293.

26: Bäumer W, Wlaź P, Jennings G, Rundfeldt C. The putative lipid raft modulator miltefosine displays immunomodulatory action in T-cell dependent dermal inflammation models. Eur J Pharmacol. 2010 Feb 25;628(1-3):226-32. Epub 2009 Nov 14. PubMed PMID: 19917276.

27: Patil V, Guerrant W, Chen PC, Gryder B, Benicewicz DB, Khan SI, Tekwani BL, Oyelere AK. Antimalarial and antileishmanial activities of histone deacetylase inhibitors with triazole-linked cap group. Bioorg Med Chem. 2010 Jan 1;18(1):415-25. Epub 2009 Oct 27. PubMed PMID: 19914074; PubMed Central PMCID: PMC2818366.

28: Maltezou HC. Drug resistance in visceral leishmaniasis. J Biomed Biotechnol. 2010;2010:617521. Epub 2009 Nov 1. Review. PubMed PMID: 19888437; PubMed Central PMCID: PMC2771279.

29: Kaur S, Sachdeva H, Dhuria S, Sharma M, Kaur T. Antileishmanial effect of cisplatin against murine visceral leishmaniasis. Parasitol Int. 2010 Mar;59(1):62-9. Epub 2009 Oct 21. PubMed PMID: 19853668.

30: Azzouz S, Maache M, Sarciron ME, Petavy AF, Osuna A. Study of the stress proteins secreted by Leishmania donovani after treatment with edelfosine, mitelfosine and ilmofosine, and morphological alterations analyzed by electronic microscopy. Parasite. 2009 Sep;16(3):215-21. PubMed PMID: 19839267.

31: Aguiar MG, Silva DL, Nunan FA, Nunan EA, Fernandes AP, Ferreira LA. Combined topical paromomycin and oral miltefosine treatment of mice experimentally infected with Leishmania (Leishmania) major leads to reduction in both lesion size and systemic parasite burdens. J Antimicrob Chemother. 2009 Dec;64(6):1234-40. Epub 2009 Oct 12. PubMed PMID: 19825819.

32: Lukác M, Mrva M, Fischer-Fodor E, Lacko I, Bukovský M, Miklásová N, Ondriska F, Devínsky F. Synthesis and biological activity of dialkylphosphocholines. Bioorg Med Chem Lett. 2009 Nov 15;19(22):6346-9. Epub 2009 Sep 24. PubMed PMID: 19818608.

33: Serrano-Martín X, Payares G, De Lucca M, Martinez JC, Mendoza-León A, Benaim G. Amiodarone and miltefosine act synergistically against Leishmania mexicana and can induce parasitological cure in a murine model of cutaneous leishmaniasis. Antimicrob Agents Chemother. 2009 Dec;53(12):5108-13. Epub 2009 Oct 5. PubMed PMID: 19805563; PubMed Central PMCID: PMC2786335.

34: Hartmann K, Siebenhaar F, Belloni B, Brockow K, Eben R, Hartmann B, Ruëff F, Schoepke N, Staubach P, Weber A, Maurer M. Effects of topical treatment with the raft modulator miltefosine and clobetasol in cutaneous mastocytosis: a randomized, double-blind, placebo-controlled trial. Br J Dermatol. 2010 Jan;162(1):185-90. Epub 2009 Aug 3. PubMed PMID: 19785605.

35: Lukác M, Mojzis J, Mojzisová G, Mrva M, Ondriska F, Valentová J, Lacko I, Bukovský M, Devínsky F, Karlovská J. Dialkylamino and nitrogen heterocyclic analogues of hexadecylphosphocholine and cetyltrimetylammonium bromide: effect of phosphate group and environment of the ammonium cation on their biological activity. Eur J Med Chem. 2009 Dec;44(12):4970-7. Epub 2009 Sep 2. PubMed PMID: 19762125.

36: Shukla AK, Singh BK, Patra S, Dubey VK. Rational approaches for drug designing against leishmaniasis. Appl Biochem Biotechnol. 2010 Apr;160(8):2208-18. Epub 2009 Sep 8. Review. PubMed PMID: 19756413.

37: Zea DF, Prager M, Figueroa RA, Miranda MC. [Mucosal complication of cutaneous leishmaniasis]. Biomedica. 2009 Mar;29(1):9-11. Spanish. PubMed PMID: 19753833.

38: da Luz RI, Vermeersch M, Dujardin JC, Cos P, Maes L. In vitro sensitivity testing of Leishmania clinical field isolates: preconditioning of promastigotes enhances infectivity for macrophage host cells. Antimicrob Agents Chemother. 2009 Dec;53(12):5197-203. Epub 2009 Sep 14. PubMed PMID: 19752271; PubMed Central PMCID: PMC2786351.

39: Saint-Pierre-Chazalet M, Ben Brahim M, Le Moyec L, Bories C, Rakotomanga M, Loiseau PM. Membrane sterol depletion impairs miltefosine action in wild-type and miltefosine-resistant Leishmania donovani promastigotes. J Antimicrob Chemother. 2009 Nov;64(5):993-1001. Epub 2009 Sep 12. PubMed PMID: 19749205.

40: Rybniker J, Goede V, Mertens J, Ortmann M, Kulas W, Kochanek M, Benzing T, Arribas JR, Fätkenheuer G. Treatment of visceral leishmaniasis with intravenous pentamidine and oral fluconazole in an HIV-positive patient with chronic renal failure--a case report and brief review of the literature. Int J Infect Dis. 2010 Jun;14(6):e522-5. Epub 2009 Sep 1. PubMed PMID: 19726213.

41: Soto J, Rea J, Valderrama M, Toledo J, Valda L, Ardiles J, Berman J. Efficacy of extended (six weeks) treatment with miltefosine for mucosal leishmaniasis in Bolivia. Am J Trop Med Hyg. 2009 Sep;81(3):387-9. PubMed PMID: 19706901.

42: Bianciardi P, Brovida C, Valente M, Aresu L, Cavicchioli L, Vischer C, Giroud L, Castagnaro M. Administration of miltefosine and meglumine antimoniate in healthy dogs: clinicopathological evaluation of the impact on the kidneys. Toxicol Pathol. 2009;37(6):770-5. Epub 2009 Aug 18. PubMed PMID: 19690151.

43: Riente RR, Souza VP, Carvalho SA, Kaiser M, Brun R, da Silva EF. Leishmanicidal activity of new megazol derivatives. Med Chem. 2009 Jul;5(4):392-7. PubMed PMID: 19689398.

44: de Vallière S, Mary C, Joneberg JE, Rotman S, Bullani R, Greub G, Gillmore JD, Buffet PA, Tarr PE. AA-amyloidosis caused by visceral leishmaniasis in a human immunodeficiency virus-infected patient. Am J Trop Med Hyg. 2009 Aug;81(2):209-12. Erratum in: Am J Trop Med Hyg. 2009 Oct;81(4):732. PubMed PMID: 19635871.

45: Collini P, Premchand N, Lockwood D, Greig J. Successful use of miltefosine and sodium stibogluconate, in combination, for the treatment of an HIV-positive patient with visceral leishmaniasis: a case report and brief review of the literature. Ann Trop Med Parasitol. 2009 Jul;103(5):455-9. Review. PubMed PMID: 19583915.

46: Olliaro P, Darley S, Laxminarayan R, Sundar S. Cost-effectiveness projections of single and combination therapies for visceral leishmaniasis in Bihar, India. Trop Med Int Health. 2009 Aug;14(8):918-25. Epub 2009 Jun 28. PubMed PMID: 19563434.

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48: Walochnik J, Obwaller A, Gruber F, Mildner M, Tschachler E, Suchomel M, Duchêne M, Auer H. Anti-acanthamoeba efficacy and toxicity of miltefosine in an organotypic skin equivalent. J Antimicrob Chemother. 2009 Sep;64(3):539-45. Epub 2009 Jun 23. PubMed PMID: 19549672.

49: Vermeersch M, da Luz RI, Toté K, Timmermans JP, Cos P, Maes L. In vitro susceptibilities of Leishmania donovani promastigote and amastigote stages to antileishmanial reference drugs: practical relevance of stage-specific differences. Antimicrob Agents Chemother. 2009 Sep;53(9):3855-9. Epub 2009 Jun 22. PubMed PMID: 19546361; PubMed Central PMCID: PMC2737839.

50: Wasan KM, Wasan EK, Gershkovich P, Zhu X, Tidwell RR, Werbovetz KA, Clement JG, Thornton SJ. Highly effective oral amphotericin B formulation against murine visceral leishmaniasis. J Infect Dis. 2009 Aug 1;200(3):357-60. PubMed PMID: 19545212.

51: Singh N, Gupta R, Jaiswal AK, Sundar S, Dube A. Transgenic Leishmania donovani clinical isolates expressing green fluorescent protein constitutively for rapid and reliable ex vivo drug screening. J Antimicrob Chemother. 2009 Aug;64(2):370-4. Epub 2009 Jun 12. PubMed PMID: 19525291.

52: Wadhone P, Maiti M, Agarwal R, Kamat V, Martin S, Saha B. Miltefosine promotes IFN-gamma-dominated anti-leishmanial immune response. J Immunol. 2009 Jun 1;182(11):7146-54. PubMed PMID: 19454711.

53: Barratt G, Saint-Pierre-Chazalet M, Loiseau PM. Cellular transport and lipid interactions of miltefosine. Curr Drug Metab. 2009 Mar;10(3):247-55. Review. PubMed PMID: 19442087.

54: Keynan Y, Larios OE, Wiseman MC, Plourde M, Ouellette M, Rubinstein E. Use of oral miltefosine for cutaneous leishmaniasis in Canadian soldiers returning from Afghanistan. Can J Infect Dis Med Microbiol. 2008 Nov;19(6):394-6. PubMed PMID: 19436567; PubMed Central PMCID: PMC2663468.

55: Foglia Manzillo V, Paparcone R, Cappiello S, De Santo R, Bianciardi P, Oliva G. Resolution of tongue lesions caused by Leishmania infantum in a dog treated with the association miltefosine-allopurinol. Parasit Vectors. 2009 Mar 26;2 Suppl 1:S6. PubMed PMID: 19426445; PubMed Central PMCID: PMC2679398.

56: Sarkar A, Mandal G, Singh N, Sundar S, Chatterjee M. Flow cytometric determination of intracellular non-protein thiols in Leishmania promastigotes using 5-chloromethyl fluorescein diacetate. Exp Parasitol. 2009 Aug;122(4):299-305. Epub 2009 Apr 22. PubMed PMID: 19393240.

57: González U, Pinart M, Rengifo-Pardo M, Macaya A, Alvar J, Tweed JA. Interventions for American cutaneous and mucocutaneous leishmaniasis. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD004834. Review. PubMed PMID: 19370612.

58: Pandey BD, Pandey K, Kaneko O, Yanagi T, Hirayama K. Relapse of visceral leishmaniasis after miltefosine treatment in a Nepalese patient. Am J Trop Med Hyg. 2009 Apr;80(4):580-2. PubMed PMID: 19346379.

59: Shahiduzzaman M, Dyachenko V, Obwaller A, Unglaube S, Daugschies A. Combination of cell culture and quantitative PCR for screening of drugs against Cryptosporidium parvum. Vet Parasitol. 2009 Jun 10;162(3-4):271-7. Epub 2009 Mar 13. PubMed PMID: 19342176.

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64: Das VN, Pandey K, Verma N, Lal CS, Bimal S, Topno RK, Singh D, Siddiqui NA, Verma RB, Das P. Short report: Development of post-kala-azar dermal leishmaniasis (PKDL) in miltefosine-treated visceral leishmaniasis. Am J Trop Med Hyg. 2009 Mar;80(3):336-8. PubMed PMID: 19270277.

65: Mateo M, Maynard L, Vischer C, Bianciardi P, Miró G. Comparative study on the short term efficacy and adverse effects of miltefosine and meglumine antimoniate in dogs with natural leishmaniosis. Parasitol Res. 2009 Jul;105(1):155-62. Epub 2009 Feb 24. PubMed PMID: 19238439.

66: Killingley B, Lamb LE, Davidson RN. Miltefosine to treat cutaneous leishmaniasis caused by Leishmania tropica. Ann Trop Med Parasitol. 2009 Mar;103(2):171-5. PubMed PMID: 19208301.

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68: Sánchez-Cañete MP, Carvalho L, Pérez-Victoria FJ, Gamarro F, Castanys S. Low plasma membrane expression of the miltefosine transport complex renders Leishmania braziliensis refractory to the drug. Antimicrob Agents Chemother. 2009 Apr;53(4):1305-13. Epub 2009 Feb 2. PubMed PMID: 19188379; PubMed Central PMCID: PMC2663093.

69: Avasthi R, Chaudhary SC, Khanna S. Visceral leishmaniasis simulating chronic liver disease: successful treatment with miltefosine. Indian J Med Microbiol. 2009 Jan-Mar;27(1):85-6. PubMed PMID: 19172077.

70: Mings S, Beck JC, Davidson C, Ondo AL, Shanler SD, Berman J. Cutaneous leishmaniasis with boggy induration and simultaneous mucosal disease. Am J Trop Med Hyg. 2009 Jan;80(1):3-5. PubMed PMID: 19141829.

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72: Manna L, Gravino AE, Picillo E, Decaro N, Buonavoglia C. Leishmania DNA quantification by real-time PCR in naturally infected dogs treated with miltefosine. Ann N Y Acad Sci. 2008 Dec;1149:358-60. PubMed PMID: 19120249.

73: Caccin P, Rossetto O, Montecucco C. Neurotoxicity of inverted-cone shaped lipids. Neurotoxicology. 2009 Mar;30(2):174-81. Epub 2008 Dec 9. PubMed PMID: 19114055.

74: Marco C, Jiménez-López JM, Ríos-Marco P, Segovia JL, Carrasco MP. Hexadecylphosphocholine alters nonvesicular cholesterol traffic from the plasma membrane to the endoplasmic reticulum and inhibits the synthesis of sphingomyelin in HepG2 cells. Int J Biochem Cell Biol. 2009 Jun;41(6):1296-303. Epub 2008 Nov 25. PubMed PMID: 19084611.

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76: Chakrabandhu K, Huault S, Hueber AO. Distinctive molecular signaling in triple-negative breast cancer cell death triggered by hexadecylphosphocholine (miltefosine). FEBS Lett. 2008 Dec 24;582(30):4176-84. Epub 2008 Nov 28. PubMed PMID: 19041866.

77: Kumar D, Kulshrestha A, Singh R, Salotra P. In vitro susceptibility of field isolates of Leishmania donovani to Miltefosine and amphotericin B: correlation with sodium antimony gluconate susceptibility and implications for treatment in areas of endemicity. Antimicrob Agents Chemother. 2009 Feb;53(2):835-8. Epub 2008 Nov 17. PubMed PMID: 19015344; PubMed Central PMCID: PMC2630609.

78: Mishra BB, Kale RR, Singh RK, Tiwari VK. Alkaloids: future prospective to combat leishmaniasis. Fitoterapia. 2009 Mar;80(2):81-90. Epub 2008 Oct 31. Review. PubMed PMID: 19015012.

79: Neuber H. Leishmaniasis. J Dtsch Dermatol Ges. 2008 Sep;6(9):754-65. Review. English, German. PubMed PMID: 19000063.

80: Maltezou HC. Visceral leishmaniasis: advances in treatment. Recent Pat Antiinfect Drug Discov. 2008 Nov;3(3):192-8. Review. PubMed PMID: 18991801.

81: Hornillos V, Carrillo E, Rivas L, Amat-Guerri F, Acuña AU. Synthesis of BODIPY-labeled alkylphosphocholines with leishmanicidal activity, as fluorescent analogues of miltefosine. Bioorg Med Chem Lett. 2008 Dec 15;18(24):6336-9. Epub 2008 Nov 1. PubMed PMID: 18990566.

82: Tipparaju SK, Joyasawal S, Pieroni M, Kaiser M, Brun R, Kozikowski AP. In pursuit of natural product leads: synthesis and biological evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxyl ic acid (A-33853) and its analogues: discovery of N-(2-benzoxazol-2-ylphenyl)benzamides as novel antileishmanial chemotypes. J Med Chem. 2008 Dec 11;51(23):7344-7. PubMed PMID: 18989953.

83: Saraiva VB, Wengert M, Gomes-Quintana E, Heise N, Caruso-Neves C. Na(+)-ATPase and protein kinase C are targets to 1-O-hexadecylphosphocoline (miltefosine) in Trypanosoma cruzi. Arch Biochem Biophys. 2009 Jan 1;481(1):65-71. Epub 2008 Oct 21. PubMed PMID: 18983813.

84: Guffanti M, Gaiera G, Bossolasco S, Ceserani N, Ratti D, Cinque P, Salmaso F, Gianotti N, Lazzarin A. Post-Kala-Azar dermal leishmaniasis in an HIV-1-infected woman: recovery after amphotericin B following failure of oral miltefosine. Am J Trop Med Hyg. 2008 Nov;79(5):715-8. PubMed PMID: 18981510.

85: Aichelburg AC, Walochnik J, Assadian O, Prosch H, Steuer A, Perneczky G, Visvesvara GS, Aspöck H, Vetter N. Successful treatment of disseminated Acanthamoeba sp. infection with miltefosine. Emerg Infect Dis. 2008 Nov;14(11):1743-6. PubMed PMID: 18976559; PubMed Central PMCID: PMC2630722.

86: Costa Filho AV, Lucas IC, Sampaio RN. [Comparative study between oral miltefosine and parenteral N-metil glucamine antimoniate for the treatment of experimental leishmaniasis caused Leishmania (Leishmania) amazonensis]. Rev Soc Bras Med Trop. 2008 Jul-Aug;41(4):424-7. Portuguese. PubMed PMID: 18853022.

87: Gianotti N, Maillard M, Gaiera G, Bestetti A, Cernuschi M, De Bona A, Lazzarin A, Cinque P, Bossolasco S. Leishmania infection can hamper immune recovery in virologically suppressed HIV-infected patients. New Microbiol. 2008 Jul;31(3):435-8. PubMed PMID: 18843901.

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