Miltefosine
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03908 |
| CAS | 58066-85-6 |
| Molecular Weight | 407.57 |
| Molecular Formula | C21H46NO4P |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-03908 | 5 g | $299 | In stock |
Online Inquiry
Add to cartDescription
Miltefosine inhibits PI3K/Akt activity with ED50 of 17.2 μM and 8.1 μM in carcinoma cell lines A431 and HeLa, first oral drug for Visceral leishmaniasis, effective against both promastigotes and amastigotes.
Specification
| Synonyms | n-hexadecylphosphocholine; Hexadecylphosphocholine; Miltex; Impavido; 2-[[(Hexadecyloxy)hydroxyphosphinyl]oxy]-N,N,N-trimethylethanaminium; MAPCHO®-16; C-16Miltefosine |
| Storage | Store at -20°C |
| IUPAC Name | hexadecyl 2-(trimethylazaniumyl)ethyl phosphate |
| Canonical SMILES | CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C |
| 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 |
Properties
| Appearance | White to Off-white Solid |
| Application | Antineoplastic Agents |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 223-228°C (dec.) |
| Flash Point | 320 °F |
| Solubility | Soluble in Chloroform (Slightly), Methanol (Slightly) |
Reference Reading
1.Miltefosine lipid nanocapsules: Intersection of drug repurposing and nanotechnology for single dose oral treatment of pre-patent schistosomiasis mansoni.
El-Moslemany RM1, Eissa MM2, Ramadan AA1, El-Khordagui LK1, El-Azzouni MZ3. Acta Trop. 2016 Mar 31;159:142-148. doi: 10.1016/j.actatropica.2016.03.038. [Epub ahead of print]
A dual drug repurposing/nanotechnological approach was used to develop an alternative oral treatment for schistosomiasis mansoni using miltefosine (MFS), an anticancer alkylphosphocholine, and lipid nanocapsules (LNCs) as oral nanovectors. We demonstrated earlier that MFS possesses significant activity against different developmental stages of Schistosoma mansoni in the mouse model using 5 successive 20mg/kg/day oral doses. Moreover, an effective single dose (20mg/kg) oral treatment against the adult stage of S. mansoni in mice was developed using LNCs, particularly modified with CTAB, a positive charge imparting agent (MFS-LNC-CTAB+), or oleic acid as membrane permeabilizer (MFS-LNC-OA). Efficacy enhancement involved, at least in part, targeting of the worm tegument with MFS-LNCs as a new therapeutic entity. As the tegument surface charge and composition may differ in pre-patent stages of the parasite, it was of importance in the present study to assess the efficacy of a single oral dose of the two MFS-LNC formulations against invasive and immature stages for potential advantage relative to praziquantel.
2.Investigation of Calcium Channel Blockers as Antiprotozoal Agents and Their Interference in the Metabolism of Leishmania (L.) infantum.
Reimão JQ1, Mesquita JT2, Ferreira DD2, Tempone AG2. Evid Based Complement Alternat Med. 2016;2016:1523691. doi: 10.1155/2016/1523691. Epub 2016 Jan 28.
Leishmaniasis and Chagas disease are neglected parasitic diseases endemic in developing countries; efforts to find new therapies remain a priority. Calcium channel blockers (CCBs) are drugs in clinical use for hypertension and other heart pathologies. Based on previous reports about the antileishmanial activity of dihydropyridine-CCBs, this work aimed to investigate whether the in vitro anti-Leishmania infantum and anti-Trypanosoma cruzi activities of this therapeutic class would be shared by other non-dihydropyridine-CCBs. Except for amrinone, our results demonstrated antiprotozoal activity for fendiline, mibefradil, and lidoflazine, with IC50 values in a range between 2 and 16 μM and Selectivity Index between 4 and 10. Fendiline demonstrated depolarization of mitochondrial membrane potential, with increased reactive oxygen species production in amlodipine and fendiline treated Leishmania, but without plasma membrane disruption. Finally, in vitro combinations of amphotericin B, miltefosine, and pentamidine against L.
3.A replicative in vitro assay for drug discovery against Leishmania donovani.
Tegazzini D1, Díaz R2, Aguilar F2, Peña I3, Presa JL3, Yardley V2, Martin JJ3, Coteron JM1, Croft SL2, Cantizani J4. Antimicrob Agents Chemother. 2016 Mar 28. pii: AAC.01781-15. [Epub ahead of print]
The protozoan parasiteLeishmania donovaniis the causative agent of visceral leishmaniasis, a disease potentially fatal if not treated. Current available treatments have major limitations and new and safer drugs are urgently needed. In recent years, advances in high throughput screening technologies have enabled the screening of millions of compounds to identify new antileishmanial agents. However, most of the compounds identifiedin vitrodid not translate their activity when tested inin vivomodels, highlighting the need to develop more predictivein vitroassays. In the present work, we describe the development of a robust replicative, high content,in vitrointracellularL. donovaniassay. Horse serum was included in the assay media to replace standard foetal bovine serum to completely eliminate the extracellular parasites derived from the infection process. A novel phenotypicin vitroinfection model has been developed complemented with the identification of the proliferation of intracellular amastigotes measured by EdU incorporation.
4.Febrifugine analogues as Leishmania donovani trypanothione reductase inhibitors: binding energy analysis assisted by molecular docking, ADMET and molecular dynamics simulation.
Pandey RK1, Kumbhar BV2, Srivastava S3, Malik R3, Sundar S4, Kunwar A2, Prajapati VK1. J Biomol Struct Dyn. 2016 Apr 4:1-18. [Epub ahead of print]
Visceral leishmaniasis affects people from 70 countries worldwide, mostly from Indian, African and south American continent. The increasing resistance to antimonial, miltefosine and frequent toxicity of amphotericin B drives an urgent need to develop an antileishmanial drug with excellent efficacy and safety profile. In this study we have docked series of febrifugine analogues (n = 8813) against trypanothione reductase in three sequential docking modes. Extra precision docking resulted into 108 ligands showing better docking score as compared to two reference ligand. Furthermore, 108 febrifugine analogues and reference inhibitor clomipramine were subjected to ADMET, QikProp and molecular mechanics, the generalized born model and solvent accessibility study to ensure the toxicity caused by compounds and binding-free energy, respectively. Two best ligands (FFG7 and FFG2) qualifying above screening parameters were further subjected to molecular dynamics simulation.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
