Miltefosine

Miltefosine Basic information
Product Name:Miltefosine
Synonyms:2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-n,n,n-trimethyl-ethanaminiuhydrox;2-(((hexadecyloxy)hydroxyphosphinyl)oxy)-n,n,n-trimethylethanaminiumhydroxid;cholinephosphate,hexadecylester,hydroxide,innersalt;d18506;Hexadecyl 2-(trimethylamino)ethyl phosphate;Miltex;13-18506;2-[[(Hexadecyloxy)hydroxyphasphinyl]oxy]-N,N,N-trimethylethanaminiminner salt
CAS:58066-85-6
MF:C21H46NO4P
MW:407.57
EINECS:622-572-6
Product Categories:Inhibitors;Anti-cancer&immunity;Anti-virals;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators;Miscellaneous Natural Products;MILTEX;inhibitor;58066-85-6;Glycon Biochem
Mol File:58066-85-6.mol
Miltefosine Structure
Miltefosine Chemical Properties
Melting point 232-234° (dec)
storage temp. room temp
solubility H2O: soluble10mg/mL, clear, colorless
form Crystalline solid
color White to Almost white
InChIInChI=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
InChIKeyPQLXHQMOHUQAKB-UHFFFAOYSA-N
SMILESO(CCCCCCCCCCCCCCCC)P([O-])(=O)OCC[N+](C)(C)C
CAS DataBase Reference58066-85-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22-43
Safety Statements 36/37
RIDADR UN 2811 6.1 / PGIII
WGK Germany 3
RTECS KH2890000
HS Code 29239000
ToxicityLD50 in rats (mg/kg): 246 orally (Muschiol)
MSDS Information
Miltefosine Usage And Synthesis
DescriptionMiltefosin, representing the prototype of a new phospholipid structure, was introduced for the palliative treatment of skin metastases in patients with breast cancer. It is highly active against the human leukemia tumor cells xenograft in nude mice, leading to growth inhibition and regression of large established tumors. Its mode of antitumor activity is not mediated by the host immune system but by its pharmacological effects at the level of the cancer cell membrane, distinctly different from that of the classical cytostatic drugs which interact with cell proliferation at the level of DNA replication. Protein kinase C inhibition has been suggested as a possible mechanism.
OriginatorAsta Medica (Germany)
UsesA phospholipid drug with antineoplastic and antiprotozoal/antifungal properties, also acts as an Akt inhibitor, and under investigation as a potential therapy against HIV infection.
DefinitionChEBI: A phospholipid that is the hexadecyl monoester of phosphocholine.
Brand nameMiltex
Antimicrobial activityConcentrations of 1–5 μm inhibit the promastigotes and amastigotes of Leishmania spp. and the epimastigotes and amastigotes of T. cruzi. Inhibitory concentrations against T. brucei spp. and E. histolytica are closer to 50 μm. Acanthamoeba spp. are variably susceptible, depending on the experimental conditions.
Acquired resistanceThere are no reports of clinical resistance in Leishmania so far. Experimental resistance has been induced in vitro against the promastigote stage of Leishmania and two plasma membrane proteins, LdMT and Ld Ros3, are necessary for miltefosine uptake. There is evidence that reduced sensitivity of promastigotes is passed on to intracellular amastigotes.
Pharmaceutical ApplicationsAn alkylphospholipid, originally investigated as an anticancer compound, formulated for oral administration.
Biochem/physiol ActionsInhibitor of protein kinase C and of phosphatidylcholine synthesis. Used for the treatment of visceral and cutaneous leishmaniasis. Active against metronidazole-resistant and -susceptible strains of Trichomonas vaginalis
PharmacokineticsIn rodent models the drug is almost completely absorbed after oral administration. About 90% is bound to plasma proteins. It is widely distributed in the body; studies in rats showed highest uptake in kidney, liver and spleen. In rats and dogs bioavailability was 82% and 94%, with maximum values reached after 4–48 h.
In adult human trials repeated oral dosing with 100 mg per day achieved a peak plasma concentration of 70 mg/L after 8–24 h (day 23). The half-life is 6–8 days.
Clinical UseVisceral leishmaniasis
Cutaneous leishmaniasis
Side effectsMild to moderate gastrointestinal side effects are reported in 40–60% of patients. Moderate to severe nephrotoxicity was seen in 2% and 1% of patients, respectively; increases in creatinine levels were reversible. Miltefosine is contraindicated in pregnancy, based on findings of teratogenicity in rats. It causes hemolysis and cannot be given intravenously.
storage-20°C
Miltefosine Preparation Products And Raw materials
Raw materialsTrimethylamine-->SULPHOSUCCINIC ACID ESTER-->1-Hexadecanol
Tylosin phosphate Triethyl phosphate AMPHISOL A CHOLINE OCTADECYL PHOSPHATE Methyl 2-hydroxyethyl cellulose DIHYDROSPHINGOSYLPHOSPHORYLCHOLINE ROCK PHOSPHATE Tributyl phosphate Trisodium phosphate Tris(2-chloroethyl) phosphate 2-Butanone CHOLESTERYL PHOSPHORYL CHOLINE Miltefosine DIHYDROSPHINGOSINE PHOSPHOCHOLINE, [4,5-3H] phosphate Ethyl acetate Tris(hydroxymethyl)aminomethane N,N-Dimethyl-1,4-phenylenediamine

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