| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H46NO4P |
| Molecular Weight | 407.568 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C
InChI
InChIKey=PQLXHQMOHUQAKB-UHFFFAOYSA-N
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
| Molecular Formula | C21H46NO4P |
| Molecular Weight | 407.568 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Miltefosine is an anti-leishmanial agent. It is an alkyl phospholipids compound, was originally intended for breast cancer and other solid tumors. However, it could not be developed as an oral agent because of dose-limiting gastro-intestinal toxicity, and only a topical formulation is approved for skin metastasis. But Miltefosine showed excellent antileishmanial activity both in vitro and in experimental models. Miltefosine is effective in vitro against both promastigotes and amastigotes of various species of Leishmania and also other kinetoplastidae (Trypanosoma cruzi,T. brucei) and other protozoan parasites (Entamoeba histolytica, Acanthamoeba). Mechanism of action is unknown. It is likely to involve interaction with lipids (phospholipids and sterols), including membrane lipids, inhibition of cytochrome c oxidase (mitochondrial function), and apoptosis-like cell death. Miltefosine is approved for the treatment of Visceral leishmaniasis (due to Leishmania donovani), Cutaneous leishmaniasis (due to Leishmania braziliensis, Leishmania guyanensis, and Leishmania panamensis) and Mucosal leishmaniasis (due to Leishmania braziliensis).
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
PubMed
Sample Use Guides
For adults and adolescents ≥12 years of age weighing 30 to 44 kg - one 50 mg capsule twice daily for 28 consecutive days, 45 kg or greater - one 50 mg capsule three times daily for 28 consecutive days. Administer with food to ameliorate gastrointestinal adverse reactions.
Route of Administration:
Oral
Miltefosine was tested in vitro against L. donovani promastigotes. The cells death profile was initially slow when concentrations up to 20 mkM were used. Subsequently, a very rapid and dose-dependent death occurred with miltefosine concentrations between 20 and 50 mkM, reaching approximately 100% at around 40 mkM. Approximately 50% death was observed with miltefosine at a concentration of 25 mkM.
