Miltefosine (CED0003930)

Record Information
Version1.0
Creation Date2016-05-22 05:25:25 UTC
Update Date2026-05-14 19:01:51 UTC
Accession NumberCHEM018656
Identification
Common NameMiltefosine
ClassSmall Molecule
Description
Miltefosine (C21H46NO4P) is an organic compound with an average molecular weight of 407.58 g/mol. Miltefosine belongs to the quaternary ammonium salts, a subclass of organonitrogen compounds within the organic compounds. This substance is identified as a treatment for leishmaniasis (PMC13305352, PMC8270272) and breast cancer (PMC3541582). Regarding its biological activity, it acts as a protein target inhibitor/substrate of ATP-dependent translocase ABCB1 and targets Phospholipase A2 (PLA2G1B). The compound is found in or released from 16 recorded sources. These include healthcare, pharmaceuticals & veterinary products, specifically as antiprotozoals, and food, food processing & cookware for food preservation. It is also associated with building & construction materials such as roofs and floors, and household cleaning & consumer products including tobacco smoke filters and perfumes within detergents and soaps. Additionally, it is found in electrical & electronic equipment, including electrodes, electric switches, emergency protective devices, conductors or conductive bodies characterised by the conductive materials, and colour television systems. The recorded exposure route for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HexadecylphosphocholineChEBI
HexadecylphosphorylcholineChEBI
MiltefosinaChEBI
MiltefosinumChEBI
MonohexadecylphosphocholineChEBI
MonohexadecylphosphorylcholineChEBI
ImpavidoKegg
HDPCMeSH
MiltexMeSH
N-HexadecylphosphorylcholineMeSH
Chemical FormulaC21H46NO4P
Average Molecular Mass407.576 g/mol
Monoisotopic Mass407.316 g/mol
CAS Registry Number58066-85-6
IUPAC Namehexadecyl 2-(trimethylazaniumyl)ethyl phosphate
Traditional Namemiltex
SMILESCCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C
InChI IdentifierInChI=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
InChI KeyPQLXHQMOHUQAKB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentPhosphocholines
Alternative Parents
Substituents
  • Phosphocholine
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Tetraalkylammonium salt
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP2.68ALOGPS
logP2.25ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.59 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity125.51 m³·mol⁻¹ChemAxon
Polarizability50.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dj-9432000000-642b57f37f036f7f50c3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0550-9061400000-e095141ca899b073c533Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-5690000000-7d225d53e68dce85d25bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9410000000-f258e2588380399fafa5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0003900000-1691b838c8f926e3c434Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kor-2019200000-4631320f9dcefaac10a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9011000000-f7696a7826d1d702049dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
217.0Log mg/kg[120:390]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
leishmaniasisis_treatment_forNot AvailablePMC13305352 , PMC8270272
breast canceris_treatment_forNot AvailablePMC3541582
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
385AntiprotozoalsHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Miltefosine Drug Metabolism Action Pathway
Miltefosine Drug Metabolism Action Pathway
Miltefosine Predicted Metabolism Pathway
Miltefosine Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)178.82
Click to view 3D structurePhospholipase A2, major isoenzymeP00592Sus scrofaPredicted (SEA)1.55698
Lysophosphatidic acid receptor 2 structureClick to view 3D structureLysophosphatidic acid receptor 2Q9HBW0HumansPredicted (SEA)6.38364
Click to view 3D structureLysophosphatidic acid receptor 3Q9UBY5HumansPredicted (SEA)7.78492
Click to view 3D structurePhospholipase BQ9P8P2Cryptococcus neoformansPredicted (SEA)0.467095
UDP-3-O-acyl-N-acetylglucosamine deacetylase structureClick to view 3D structureUDP-3-O-acyl-N-acetylglucosamine deacetylaseO67648Aquifex aeolicus (strain VF5)Predicted (SEA)34.0201
Sphingosine 1-phosphate receptor 1 structureClick to view 3D structureSphingosine 1-phosphate receptor 1P21453HumansPredicted (SEA)68.0402
Click to view 3D structureSodium- and chloride-dependent creatine transporter 1P28570Rattus norvegicusPredicted (SEA)0.389246
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseB7UJP3Escherichia coli O127:H6 (strain E2348/69 / EPEC)Predicted (SEA)0.389246
Click to view 3D structureMitochondrial carnitine/acylcarnitine carrier proteinO43772HumansPredicted (SEA)3.03612
Lysophosphatidic acid receptor 1 structureClick to view 3D structureLysophosphatidic acid receptor 1Q92633HumansPredicted (SEA)13.7793
Geranylgeranyl pyrophosphate synthase structureClick to view 3D structureGeranylgeranyl pyrophosphate synthaseO95749HumansPredicted (SEA)4.98235
Click to view 3D structureFarnesyl pyrophosphate synthaseQ0GKD7Leishmania donovaniPredicted (SEA)4.67095
Click to view 3D structureAcylcarnitine hydrolaseQ91WG0Mus musculusPredicted (SEA)2.88042
Farnesyl pyrophosphate synthase structureClick to view 3D structureFarnesyl pyrophosphate synthaseP14324HumansPredicted (SEA)6.92858
Click to view 3D structureAcetylcholinesteraseP21836Mus musculusPredicted (SEA)132.11
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)724.231
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)1274.63
Click to view 3D structureFatty-acid amide hydrolase 1O08914Mus musculusPredicted (SEA)100.036
Click to view 3D structureCocaine esteraseO00748HumansPredicted (SEA)20.5522
Autotaxin structureClick to view 3D structureAutotaxinQ13822HumansPredicted (SEA)31.3732
Lysophosphatidic acid receptor 6 structureClick to view 3D structureLysophosphatidic acid receptor 6P43657HumansPredicted (SEA)5.3716
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)868.097
Click to view 3D structureLiver carboxylesteraseQ29550Sus scrofaPredicted (SEA)11.4438
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)933.646
Concentrations
Not Available
External Links
DrugBank IDDB09031
HMDB IDHMDB0254735
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMiltefosine
Chemspider ID3473
ChEBI ID75283
PubChem Compound ID3599
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22385017
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22935677
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22995097
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23136856
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23165465
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23199340
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23239091
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23243111
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23434530
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23434716
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23468121
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23601234
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23673723
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23723490
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23729024
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23738749
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23740007
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23811261
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23811637
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23861311
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23871798
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23890327
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23930349