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Miltefosine

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Synopsis

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Chemistry

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Also known as: 58066-85-6, Hexadecylphosphocholine, Impavido, Miltex, Hdpc, Hexadecylphosphorylcholine

Molecular Formula

C₂₁H₄₆NO₄P

Molecular Weight

407.6 g/mol

InChI Key

PQLXHQMOHUQAKB-UHFFFAOYSA-N

FDA UNII

53EY29W7EC

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). (NCI04)

Miltefosine is an Antileishmanial.

1 2D Structure

Miltefosine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

2.1.2 InChI

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

2.1.3 InChI Key

PQLXHQMOHUQAKB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C

2.2 Other Identifiers

2.2.1 UNII

53EY29W7EC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. D 18506

2. D-18506

3. D18506

4. Hdpc

5. Hexadecylphosphocholine

6. Impavido

7. Miltex

8. N-hexadecylphosphorylcholine

2.3.2 Depositor-Supplied Synonyms

1. 58066-85-6

2. Hexadecylphosphocholine

3. Impavido

4. Miltex

5. Hdpc

6. Hexadecylphosphorylcholine

7. N-hexadecylphosphorylcholine

8. Miltefosinum

9. Miltefosina

10. 1-hexadecylphosphorylcholine

11. Hexadecyl 2-(trimethylammonio)ethyl Phosphate

12. Hexadecyl Phosphocholine

13. Miltefosin C

14. N-hexadecylphosphocholine

15. D-18506

16. Hexadecyl 2-(trimethylazaniumyl)ethyl Phosphate

17. Miltefosin

18. Nsc605583

19. Hexadecyl (2-(trimethylammonio)ethyl) Phosphate

20. Miltefosine (inn)

21. Monohexadecylphosphocholine

22. Chembl125

23. Nsc-605583

24. Nsc-758968

25. Monohexadecylphosphorylcholine

26. Hepc;hexadecyl Phosphocholine

27. 53ey29w7ec

28. Chebi:75283

29. Mmv688990

30. Ncgc00095169-01

31. Miltefos

32. Miltefosine [inn]

33. Dsstox_cid_25942

34. Dsstox_rid_81240

35. Dsstox_gsid_45942

36. Miltefosinum [inn-latin]

37. Miltefosina [inn-spanish]

38. C21h46no4p

39. Miltefosine [inn:ban]

40. Fos-choline 16

41. Cas-58066-85-6

42. D 18506

43. Brn 3690495

44. Unii-53ey29w7ec

45. Miltextrade Mark

46. Hepc Hydrate

47. Impavidotrade Mark

48. D18506

49. Impavido (tn)

50. Choline, Inner Salt

51. Mfcd00133396

52. Tf-002

53. 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-n,n,n-trimethylethanaminium Hydroxide, Inner Salt

54. Nsc 605583

55. Choline Hydroxide, Hexadecyl Hydrogen Phosphate, Inner Salt

56. Choline Phosphate, Hexadecyl Ester, Hydroxide, Inner Salt

57. Miltefosine [mi]

58. Hexadecyl Phosphorylcholine

59. H-1850

60. M-7200

61. Ethanaminium, 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-n,n,n-trimethyl-, Hydroxide, Inner Salt

62. Miltefosine [mart.]

63. Schembl26215

64. Miltefosine [who-dd]

65. 4-04-00-01460 (beilstein Handbook Reference)

66. Spectrum1505329

67. Dtxsid7045942

68. Gtpl11355

69. Miltefosine [orange Book]

70. Hexadecyl Phosphorylcholine Hydrate

71. Hms1922d16

72. Hms2089j15

73. Hms3649i09

74. Pharmakon1600-01505329

75. Hexadecylphosphocholine, Miltefosine

76. Bcp04506

77. Miltefosine (hexadecylphosphocholine)

78. Tox21_111466

79. Bdbm50034220

80. Ccg-35584

81. Ccg-36097

82. Ccg-40025

83. Dl-131

84. Hexadecyl 2-(trimethyl-.lambda.~5~-azanyl)ethyl Hydrogen Phosphate

85. Nsc758968

86. S3056

87. 1-n-hexadecylphosphorylcholine

88. Akos015914886

89. Tox21_111466_1

90. Bcp9000927

91. Db09031

92. Ncgc00095169-02

93. Ncgc00095169-03

94. Ncgc00095169-05

95. Ncgc00095169-07

96. Hy-13685

97. Bcp0726000071

98. Ft-0608148

99. M2445

100. Hexadecyloxy-2-trimethylammonioethylphosphorate

101. D02494

102. Ab00642217-03

103. Ab00642217_04

104. Miltefosine, >=98% (perchloric Acid Titration)

105. A831718

106. Q411787

107. Hexadecyl 2-(trimethylammonio)ethyl Phosphate Hydrate

108. 2-[hexadecoxy(hydroxy)phosphoryl]oxyethyl-trimethyl-ammonium

109. Phosphoric Acid Hexadecyl 2-(trimethylammonio)ethyl Ester

110. [2-(hexadecyloxy-hydroxy-phosphoryloxy)-ethyl]-trimethyl-ammonium

111. 3, 4-hydroxy-n,n,n-trimethyl-, Hydroxide, Inner Salt, 4-oxide

112. Hexadecyl 2-(trimethyl-lambda~5~-azanyl)ethyl Hydrogen Phosphate

113. Phosphoric Acid Hexadecyl 2-(trimethylammonio)ethyl Ester Hydrate

114. 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-n,n,n-trimethylethanaminium Hydroxide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₄₆NO₄P
Molecular Weight	407.6 g/mol
XLogP3	6.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	20
Exact Mass	407.31644595 g/mol
Monoisotopic Mass	407.31644595 g/mol
Topological Polar Surface Area	58.6 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	363
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Impavido
PubMed Health	miltefosine
Drug Classes	Anti-Infective Agent
Active Ingredient	Miltefosine

2 of 2
Drug Name	Impavido
PubMed Health	miltefosine
Drug Classes	Anti-Infective Agent
Active Ingredient	Miltefosine

4.2 Drug Indication

For the treatment of mucosal (caused by Leishmania braziliensis), cutaneous (caused by L. braziliensis, L. guyanensis, and L. panamensis), and visceral leishmaniasis (caused by L. donovani). In comparing Leishmania drug susceptibility, it has been found that L. donovani is the most susceptible to miltefosine while L. major is the least susceptible. Off-label use includes treatment of free-living amebae (FLA) infections (unlabeled use; CDC, 2013).

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Little is known about the clinical pharmacodynamics of miltefosine and other antileishmanial drugs.

5.2 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

MILTEFOSINE

5.3.2 FDA UNII

53EY29W7EC

5.3.3 Pharmacological Classes

Antileishmanial [EPC]

5.4 ATC Code

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01C - Agents against leishmaniasis and trypanosomiasis

P01CX - Other agents against leishmaniasis and trypanosomiasis

P01CX04 - Miltefosine

5.5 Absorption, Distribution and Excretion

Absorption

After oral administration, miltefosine is slowly absorbed from the gastrointestinal tract with an absolute bioavailability of 82% in rats and 94% in dogs. Absolute bioavailability has not been assessed in humans, however GI absorption rate in a two-compartment model is estimated to be 0.416 hr-1.

Route of Elimination

Miltefosine is almost completely eliminated by degradation via phospholipase D. Drug keeps accumulating until the end of treatment due to the extremely slow elimination, as seen by the long elimination half lives.

Volume of Distribution

Radioactivity studies have found that miltefosine has a wide distribution with high levels in the kidney, intestinal mucosa, liver, and spleen.

Clearance

Plasma clearance is very low and the terminal elimination half life was found to be 84 and 159 hours in rats and dogs respectively.

5.6 Metabolism/Metabolites

Miltefosine is metabolized mainly by phospholipase D, releasing choline, choline-containing metabolites, and hexadecanol, which are likely to enter the intermediary metabolism. The metabolites produced by this reaction are all endogenous and are likely used for bio-synthesis of acetylcholine, cell membranes, and long-chain fatty acids.

5.7 Biological Half-Life

The primary elimination half life is 7.05 days (range: 5.45-9.10 days) and the terminal half-life is 30.9 days (range: 30.8-31.2 days).

5.8 Mechanism of Action

Miltefosine has demonstrated activity against Leishmania parasites and neoplastic cells primarily due to its effects on apoptosis and disturbance of lipid-dependent cell signalling pathways. Several potential antileishmanial mechanisms of action have been proposed, however no mechanism has been identified definitely. Within the mitochondria, miltefosine inhibits cytochrome-c oxidase leading to mitochondrial dysfunction and apoptosis-like cell death. Antineoplastic mechanisms of action are related to antileishmanial targets and include inhibition of phosphatidylcholine biosynthesis and inhibition of Akt (also known as protein kinase B), which is a crucial protein within the PI3K/Akt/mTOR intracellular signalling pathway involved in regulating the cell cycle. Animal studies also suggest it may be effective against Trypanosome cruzi (the organism responsible for Chagas' disease), metronidazole-resistant strains of Trichonomas vaginalis, and it may have broad-spectrum anti-fungal activity.

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