miltefosine   Click here for help

GtoPdb Ligand ID: 11355

Synonyms: D-18506 | D18506 | Impavido® | Miltex® | n-hexadecylphosphorylcholine
Approved drug Immunopharmacology Ligand
miltefosine is an approved drug (FDA (2014))
Compound class: Synthetic organic
Comment: Miltefosine is an antiprotozoal (anthelmintic) drug that is primarily used to treat leishmaniasis. It has additional anticancer and immunomodulatory/anti-inflammatory activities [2]. The antitumour activity of miltefosine is principally mediated through the inhibition of Akt phosphorylation [4], which exerts a modulatory effect on the phosphatidylinositol 3-kinase (PI3K)-Akt/PKB cellular survival pathway.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 20
Topological polar surface area 68.4
Molecular weight 407.32
XLogP 6.63
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-]
Isomeric SMILES CCCCCCCCCCCCCCCCOP(=O)(OCC[N+](C)(C)C)[O-]
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
InChI Key PQLXHQMOHUQAKB-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
hexadecyl 2-(trimethylazaniumyl)ethyl phosphate
International Nonproprietary Names Click here for help
INN number INN
6362 miltefosine
Synonyms Click here for help
D-18506 | D18506 | Impavido® | Miltex® | n-hexadecylphosphorylcholine
Database Links Click here for help
BindingDB Ligand 50034220
CAS Registry No. 58066-85-6 (source: PubChem)
ChEMBL Ligand CHEMBL125
DrugBank Ligand DB09031
GtoPdb PubChem SID 440816724
PubChem CID 3599
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