Details
| 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
DescriptionCurator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=18472998; http://www.ncbi.nlm.nih.gov/pubmed/?term=11355955; http://www.ncbi.nlm.nih.gov/pubmed/?term=16730362
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=18472998; http://www.ncbi.nlm.nih.gov/pubmed/?term=11355955; http://www.ncbi.nlm.nih.gov/pubmed/?term=16730362
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).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: UNIPROT: B7TYN7 (Cytochrome c oxidase subunit 1) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | IMPAVIDO Approved UseIndicated in adults and adolescents ≥12 years of age weighing ≥ 30 kg for the treatment of visceral leishmaniasis caused by Leishmania donovani; Cutaneous leishmaniasis caused by Leishmania braziliensis, Leishmania guyanensis, and Leishmania panamensis; Mucosal leishmaniasis caused by Leishmania braziliensis. Launch Date2014 |
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| Curative | IMPAVIDO Approved UseIndicated in adults and adolescents ≥12 years of age weighing ≥ 30 kg for the treatment of visceral leishmaniasis caused by Leishmania donovani; Cutaneous leishmaniasis caused by Leishmania braziliensis, Leishmania guyanensis, and Leishmania panamensis; Mucosal leishmaniasis caused by Leishmania braziliensis. Launch Date2014 |
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| Curative | IMPAVIDO Approved UseIndicated in adults and adolescents ≥12 years of age weighing ≥ 30 kg for the treatment of visceral leishmaniasis caused by Leishmania donovani; Cutaneous leishmaniasis caused by Leishmania braziliensis, Leishmania guyanensis, and Leishmania panamensis; Mucosal leishmaniasis caused by Leishmania braziliensis. Launch Date2014 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
66.2 μg/mL |
50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
37.3 μg/mL |
50 mg 3 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
636 μg × h/mL |
50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
295 μg × h/mL |
50 mg 3 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.4 day |
50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.8 day |
50 mg 3 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2% |
50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2% |
50 mg 3 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MILTEFOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
Disc. AE: AST increased, ALT increased... AEs leading to discontinuation/dose reduction: AST increased (0.8%) Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159ALT increased (0.8%) Vomiting (0.8%) Anorexia (0.8%) Blood urea nitrogen increased (0.8%) Creatinine increased (0.8%) Oliguria (0.8%) |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, at least 12 years of age n = 299 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Sex: M+F Population Size: 299 Sources: |
Disc. AE: Stevens-Johnson syndrome, Rash... AEs leading to discontinuation/dose reduction: Stevens-Johnson syndrome (0.3%) Sources: Rash (0.3%) Diarrhea (grade 4, 0.3%) Hyperbilirubinemia (0.3%) Thrombocytopenia (0.3%) Arthritis (0.3%) |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: Page: applications/Miltefosine_application.pdf - p.13 |
unhealthy, median age of 25 years n = 89 Health Status: unhealthy Condition: leishmaniasis Age Group: median age of 25 years Sex: M+F Population Size: 89 Sources: Page: applications/Miltefosine_application.pdf - p.13 |
Disc. AE: Motion sickness, Headache... AEs leading to discontinuation/dose reduction: Motion sickness (1.1%) Sources: Page: applications/Miltefosine_application.pdf - p.13Headache (1.1%) |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: Page: applications/Miltefosine_application.pdf - p.14 |
unhealthy, median age of 25 years n = 89 Health Status: unhealthy Condition: leishmaniasis Age Group: median age of 25 years Sex: M+F Population Size: 89 Sources: Page: applications/Miltefosine_application.pdf - p.14 |
Other AEs: Vomiting, Vomiting... Other AEs: Vomiting (grade 3-4, 3%) Sources: Page: applications/Miltefosine_application.pdf - p.14Vomiting (grade 4-5, 3%) |
300 mg 1 times / week multiple, oral MTD Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: |
unhealthy, median age of 56 years n = 15 Health Status: unhealthy Condition: cancer Age Group: median age of 56 years Sex: M+F Population Size: 15 Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (grade 3, 6.7%) Sources: Vomiting (grade 3, 6.7%) Diarrhoea (grade 3, 6.7%) |
50 mg 3 times / day multiple, oral (mean) Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age of 58 years n = 54 Health Status: unhealthy Condition: cancer Age Group: median age of 58 years Sex: M+F Population Size: 54 Sources: |
DLT: Nausea, Vomiting... Dose limiting toxicities: Nausea (grade 1-2) Sources: Vomiting (grade 1-2) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| ALT increased | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
| AST increased | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
| Anorexia | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
| Blood urea nitrogen increased | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
| Creatinine increased | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
| Oliguria | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
| Vomiting | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral (mean) Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
unhealthy, at least 12 years of age n = 120 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Population Size: 120 Sources: Page: nda/2014/204684Orig1s000MedR.pdf - p.159 |
| Arthritis | 0.3% Disc. AE |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, at least 12 years of age n = 299 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Sex: M+F Population Size: 299 Sources: |
| Hyperbilirubinemia | 0.3% Disc. AE |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, at least 12 years of age n = 299 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Sex: M+F Population Size: 299 Sources: |
| Rash | 0.3% Disc. AE |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, at least 12 years of age n = 299 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Sex: M+F Population Size: 299 Sources: |
| Stevens-Johnson syndrome | 0.3% Disc. AE |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, at least 12 years of age n = 299 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Sex: M+F Population Size: 299 Sources: |
| Thrombocytopenia | 0.3% Disc. AE |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, at least 12 years of age n = 299 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Sex: M+F Population Size: 299 Sources: |
| Diarrhea | grade 4, 0.3% Disc. AE |
50 mg 2 times / day multiple, oral Studied dose Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: |
unhealthy, at least 12 years of age n = 299 Health Status: unhealthy Condition: leishmaniasis Age Group: at least 12 years of age Sex: M+F Population Size: 299 Sources: |
| Headache | 1.1% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: Page: applications/Miltefosine_application.pdf - p.13 |
unhealthy, median age of 25 years n = 89 Health Status: unhealthy Condition: leishmaniasis Age Group: median age of 25 years Sex: M+F Population Size: 89 Sources: Page: applications/Miltefosine_application.pdf - p.13 |
| Motion sickness | 1.1% Disc. AE |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: Page: applications/Miltefosine_application.pdf - p.13 |
unhealthy, median age of 25 years n = 89 Health Status: unhealthy Condition: leishmaniasis Age Group: median age of 25 years Sex: M+F Population Size: 89 Sources: Page: applications/Miltefosine_application.pdf - p.13 |
| Vomiting | grade 3-4, 3% | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: Page: applications/Miltefosine_application.pdf - p.14 |
unhealthy, median age of 25 years n = 89 Health Status: unhealthy Condition: leishmaniasis Age Group: median age of 25 years Sex: M+F Population Size: 89 Sources: Page: applications/Miltefosine_application.pdf - p.14 |
| Vomiting | grade 4-5, 3% | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: Page: applications/Miltefosine_application.pdf - p.14 |
unhealthy, median age of 25 years n = 89 Health Status: unhealthy Condition: leishmaniasis Age Group: median age of 25 years Sex: M+F Population Size: 89 Sources: Page: applications/Miltefosine_application.pdf - p.14 |
| Diarrhoea | grade 3, 6.7% | 300 mg 1 times / week multiple, oral MTD Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: |
unhealthy, median age of 56 years n = 15 Health Status: unhealthy Condition: cancer Age Group: median age of 56 years Sex: M+F Population Size: 15 Sources: |
| Nausea | grade 3, 6.7% | 300 mg 1 times / week multiple, oral MTD Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: |
unhealthy, median age of 56 years n = 15 Health Status: unhealthy Condition: cancer Age Group: median age of 56 years Sex: M+F Population Size: 15 Sources: |
| Vomiting | grade 3, 6.7% | 300 mg 1 times / week multiple, oral MTD Dose: 300 mg, 1 times / week Route: oral Route: multiple Dose: 300 mg, 1 times / week Sources: |
unhealthy, median age of 56 years n = 15 Health Status: unhealthy Condition: cancer Age Group: median age of 56 years Sex: M+F Population Size: 15 Sources: |
| Nausea | grade 1-2 DLT |
50 mg 3 times / day multiple, oral (mean) Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age of 58 years n = 54 Health Status: unhealthy Condition: cancer Age Group: median age of 58 years Sex: M+F Population Size: 54 Sources: |
| Vomiting | grade 1-2 DLT |
50 mg 3 times / day multiple, oral (mean) Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age of 58 years n = 54 Health Status: unhealthy Condition: cancer Age Group: median age of 58 years Sex: M+F Population Size: 54 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
Page: - |
yes | |||
Page: - |
yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Recent strategies for the chemotherapy of visceral leishmaniasis. | 1999 Dec |
|
| Visceral leishmaniasis (kala-azar)--the Bihar (India) perspective. | 2006 Jul |
|
| Pharmacokinetics of miltefosine in Old World cutaneous leishmaniasis patients. | 2008 Aug |
|
| Miltefosine: a review of its pharmacology and therapeutic efficacy in the treatment of leishmaniasis. | 2012 Nov |
|
| Synthesis and antifungal activities of miltefosine analogs. | 2013 Sep 1 |
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.
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NCI_THESAURUS |
C2188
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WHO-ESSENTIAL MEDICINES LIST |
6.5.2
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WHO-VATC |
QL01XX09
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FDA ORPHAN DRUG |
229406
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FDA ORPHAN DRUG |
540216
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FDA ORPHAN DRUG |
590217
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NDF-RT |
N0000190851
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FDA ORPHAN DRUG |
275409
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EU-Orphan Drug |
EU/3/05/282
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WHO-ATC |
L01XX09
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FDA ORPHAN DRUG |
565016
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FDA ORPHAN DRUG |
565216
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FDA ORPHAN DRUG |
565116
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FDA ORPHAN DRUG |
843921
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605583
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53EY29W7EC
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3599
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C1170
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58066-85-6
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6362
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53EY29W7EC
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m7549
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75283
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1810
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Miltefosine
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C039128
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SUB08969MIG
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100000091387
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DB09031
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1494066
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DTXSID7045942
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CHEMBL125
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758968
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PRIMARY |
ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)
