Natural Product (NP) Details

General Information of the NP (ID: NP7079)
Name
Miltefosine
Synonyms
Miltefosine; 58066-85-6; Hexadecylphosphocholine; Miltex; Impavido; Hexadecylphosphorylcholine; HDPC; n-Hexadecylphosphorylcholine; Miltefosinum; Miltefosina; hexadecyl 2-(trimethylammonio)ethyl phosphate; 1-Hexadecylphosphorylcholine; Miltefosin C; n-hexadecylphosphocholine; D-18506; miltefosin; C21H46NO4P; UNII-53EY29W7EC; NSC605583; hexadecyl 2-(trimethylazaniumyl)ethyl phosphate; hexadecyl (2-(trimethylAmmonio)ethyl) phosphate; monohexadecylphosphocholine; CHEMBL125; monohexadecylphosphorylcholine; HePC;Hexadecyl phosphocholine; 53EY29W7EC; CHEBI:75283; MFCD00133396; MMV688990; NSC-605583; NCGC00095169-01; Miltefos; DSSTox_CID_25942; DSSTox_RID_81240; DSSTox_GSID_45942; Miltefosinum [INN-Latin]; Miltefosina [INN-Spanish]; Miltefosine [INN:BAN]; Fos-choline 16; Miltefosine (INN); CAS-58066-85-6; D 18506; Choline hexadecyl phosphate; BRN 3690495; Miltextrade mark; HePC Hydrate; Impavidotrade mark; D18506; Impavido (TN); Choline, inner salt; Miltefosine, 98%; TF-002; 2-(((Hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium hydroxide, inner salt; NSC 605583; Choline hydroxide, hexadecyl hydrogen phosphate, inner salt; Choline phosphate, hexadecyl ester, hydroxide, inner salt (6CI); Hexadecyl Phosphorylcholine; H-1850; M-7200; Ethanaminium, 2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethyl-, hydroxide, inner salt; SCHEMBL26215; 4-04-00-01460 (Beilstein Handbook Reference); SPECTRUM1505329; ETH098; DTXSID7045942; GTPL11355; Hexadecyl Phosphorylcholine Hydrate; HMS1922D16; HMS2089J15; HMS3649I09; Pharmakon1600-01505329; hexadecylphosphocholine, miltefosine; BCP04506; miltefosine (hexadecylphosphocholine); Tox21_111466; BDBM50034220; CCG-35584; CCG-36097; CCG-40025; DL-131; Hexadecyl 2-(trimethyl-.lambda.~5~-azanyl)ethyl hydrogen phosphate; NSC758968; s3056; 1-N-HEXADECYLPHOSPHORYLCHOLINE; AKOS015914886; Tox21_111466_1; BCP9000927; DB09031; NSC-758968; NCGC00095169-02; NCGC00095169-03; NCGC00095169-05; AK163678; HY-13685; BCP0726000071; FT-0608148; M2445; hexadecyloxy-2-trimethylammonioethylphosphorate; D02494; AB00642217-03; AB00642217_04; Miltefosine, >=98% (perchloric acid titration); A831718; Q411787; Hexadecyl 2-(Trimethylammonio)ethyl Phosphate Hydrate; 2-[hexadecoxy(hydroxy)phosphoryl]oxyethyl-trimethyl-ammonium; Phosphoric Acid Hexadecyl 2-(Trimethylammonio)ethyl Ester; [2-(Hexadecyloxy-hydroxy-phosphoryloxy)-ethyl]-trimethyl-ammonium; 3, 4-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt, 4-oxide; hexadecyl 2-(trimethyl-lambda~5~-azanyl)ethyl hydrogen phosphate; Phosphoric Acid Hexadecyl 2-(Trimethylammonio)ethyl Ester Hydrate; 2-(((Hexadecyloxy)hydroxyphosphinyl)oxy)-N,N,N-trimethylethanaminium hydroxide; Ethanaminium, 2-[[(hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-, inner salt
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Species Origin Coconut leaflet phytoplasma ...     Click to Show/Hide
Coconut leaflet phytoplasma
SuperKingdom: Bacteria
Phylum: Tenericutes
Class: Mollicutes
Order: Acholeplasmatales
Family: Acholeplasmataceae
Genus: Candidatus Phytoplasma
Species: Coconut leaflet phytoplasma
Disease Leishmaniasis [ICD-11: 1F54] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C21H46NO4P
PubChem CID
3599
Canonical SMILES
CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C
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
InChIKey
PQLXHQMOHUQAKB-UHFFFAOYSA-N
CAS Number
CAS 58066-85-6
ChEBI ID
CHEBI:75283
TTD Drug ID
D00FGR
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Paromomycin      Amoebiasis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression p105  Molecule Info 
Pathway MAP
Up-regulation Expression TNF  Molecule Info 
Pathway MAP
                    In-vitro Model HEK293 CVCL_0045 Healthy Homo sapiens
                    Experimental
                    Result(s)		 The in vitro activity of paromomycin and miltefosine against host cells is TLR4 dependent.
          Lopinavi      Human immunodeficiency virus disease     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model BALB/c mice were used in this study.
                    Experimental
                    Result(s)		 LPV- MFS combination therapy can be effective in the treatment of VL/HIV co-infected patients and provides data that can help to guide a possible therapeutic strategy in VL/HIV co-infection.
Target and Pathway
Target(s) Phospholipase A2 (PLA2G1B)  Molecule Info  [4]
BioCyc Phospholipases Click to Show/Hide
KEGG Pathway Glycerophospholipid metabolism Click to Show/Hide
2 Ether lipid metabolism
3 Arachidonic acid metabolism
4 Linoleic acid metabolism
5 alpha-Linolenic acid metabolism
6 Metabolic pathways
7 Ras signaling pathway
8 Vascular smooth muscle contraction
9 Pancreatic secretion
10 Fat digestion and absorption
Pathway Interaction Database Fc-epsilon receptor I signaling in mast cells Click to Show/Hide
Reactome Acyl chain remodelling of PC Click to Show/Hide
2 Acyl chain remodelling of PE
3 Acyl chain remodelling of PI
WikiPathways Glycerophospholipid biosynthesis Click to Show/Hide
References
Reference 1 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
Reference 2 Combination of paromomycin and miltefosine promotes TLR4-dependent induction of antileishmanial immune response in vitro. J Antimicrob Chemother. 2012 Oct;67(10):2373-8.
Reference 3 Miltefosine-Lopinavir Combination Therapy Against Leishmania infantum Infection: In vitro and in vivo Approaches. Front Cell Infect Microbiol. 2019 Jun 28;9:229.
Reference 4 Novel antifungal agents, targets or therapeutic strategies for the treatment of invasive fungal diseases: a review of the literature (2005-2009). Rev Iberoam Micol. 2009 Mar 31;26(1):15-22.
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