Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H46NO4P |
Molecular Weight | 407.568 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 1 |
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 |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | NONE |
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).
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/26329128
Curator's Comment: Some blood-brain barrier penetration by miltefosine in a human, although with low-level CSF accumulation.
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 Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
Disc. AE: AST increased, ALT increased... AEs leading to discontinuation/dose reduction: AST increased (0.8%) Sources: ALT 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 Health Status: unhealthy Age Group: at least 12 years of age Sex: M+F 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: |
unhealthy, median age of 25 years Health Status: unhealthy Age Group: median age of 25 years Sex: M+F Sources: |
Disc. AE: Motion sickness, Headache... AEs leading to discontinuation/dose reduction: Motion sickness (1.1%) Sources: Headache (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: |
unhealthy, median age of 25 years Health Status: unhealthy Age Group: median age of 25 years Sex: M+F Sources: |
Other AEs: Vomiting, Vomiting... Other AEs: Vomiting (grade 3-4, 3%) Sources: Vomiting (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 Health Status: unhealthy Age Group: median age of 56 years Sex: M+F 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 Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: |
unhealthy, median age of 58 years Health Status: unhealthy Age Group: median age of 58 years Sex: M+F 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 Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
AST increased | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
Anorexia | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
Blood urea nitrogen increased | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
Creatinine increased | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
Oliguria | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
Vomiting | 0.8% Disc. AE |
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, at least 12 years of age Health Status: unhealthy Age Group: at least 12 years of age Sources: |
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 Health Status: unhealthy Age Group: at least 12 years of age Sex: M+F 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 Health Status: unhealthy Age Group: at least 12 years of age Sex: M+F 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 Health Status: unhealthy Age Group: at least 12 years of age Sex: M+F 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 Health Status: unhealthy Age Group: at least 12 years of age Sex: M+F 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 Health Status: unhealthy Age Group: at least 12 years of age Sex: M+F 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 Health Status: unhealthy Age Group: at least 12 years of age Sex: M+F 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: |
unhealthy, median age of 25 years Health Status: unhealthy Age Group: median age of 25 years Sex: M+F Sources: |
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: |
unhealthy, median age of 25 years Health Status: unhealthy Age Group: median age of 25 years Sex: M+F Sources: |
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: |
unhealthy, median age of 25 years Health Status: unhealthy Age Group: median age of 25 years Sex: M+F Sources: |
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: |
unhealthy, median age of 25 years Health Status: unhealthy Age Group: median age of 25 years Sex: M+F Sources: |
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 Health Status: unhealthy Age Group: median age of 56 years Sex: M+F 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 Health Status: unhealthy Age Group: median age of 56 years Sex: M+F 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 Health Status: unhealthy Age Group: median age of 56 years Sex: M+F Sources: |
Nausea | grade 1-2 DLT |
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: |
unhealthy, median age of 58 years Health Status: unhealthy Age Group: median age of 58 years Sex: M+F Sources: |
Vomiting | grade 1-2 DLT |
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: |
unhealthy, median age of 58 years Health Status: unhealthy Age Group: median age of 58 years Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/204684Orig1s000PharmR.pdf#page=38 Page: 38.0 |
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 | ||||
Sources: https://www.jbc.org/content/291/18/9638 Page: - |
yes | |||
Sources: https://www.nature.com/articles/6691776 Page: - |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/204684Orig1s000PharmR.pdf#page=22 Page: 22.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Synthetic analogues of irlbacholine: a novel antifungal plant metabolite isolated from Irlbachia alata. | 1999 Jun |
|
Single-dose liposomal amphotericin B in the treatment of visceral leishmaniasis in India: a multicenter study. | 2003 Sep 15 |
|
Use of Leishmania donovani field isolates expressing the luciferase reporter gene in in vitro drug screening. | 2005 Sep |
|
Hexadecylphosphocholine (miltefosine) has broad-spectrum fungicidal activity and is efficacious in a mouse model of cryptococcosis. | 2006 Feb |
|
Pharmacokinetics of miltefosine in Old World cutaneous leishmaniasis patients. | 2008 Aug |
|
Cutaneous leishmaniasis with boggy induration and simultaneous mucosal disease. | 2009 Jan |
|
Synthesis and antifungal activities of miltefosine analogs. | 2013 Sep 1 |
|
Miltefosine for visceral and cutaneous leishmaniasis: drug characteristics and evidence-based treatment recommendations. | 2015 May 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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=23416156
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:06:13 GMT 2025
by
admin
on
Wed Apr 02 09:06:13 GMT 2025
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Record UNII |
53EY29W7EC
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Record Status |
Validated (UNII)
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Record Version |
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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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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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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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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
The urinary excretion of the unchanged drug on Day 23 after repeated oral administration of miltefosine to adult patients was below 0.2% of the daily dose
URINE
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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