Miltefosine

Base Information

• Chemical Name: Miltefosine
• CAS No.: 58066-85-6
• Deprecated CAS: 93597-88-7
• Molecular Formula: C21H46NO4P
• Molecular Weight: 407.574
• Hs Code.: 29239000
• European Community (EC) Number: 622-572-6
• NSC Number: 758968,605583
• UNII: 53EY29W7EC
• DSSTox Substance ID: DTXSID7045942
• Wikipedia: Miltefosine
• Wikidata: Q411787
• NCI Thesaurus Code: C1170
• RXCUI: 1494066
• Metabolomics Workbench ID: 152100
• ChEMBL ID: CHEMBL125
• Mol file: 58066-85-6.mol

Synonyms:D 18506;D-18506;D18506;HDPC;hexadecylphosphocholine;Impavido;miltefosine;Miltex;n-hexadecylphosphorylcholine

Chemical Property of Miltefosine

Chemical Property:

• Appearance/Colour: white to off-white solid
• Melting Point: 232-234oC
• PSA: 68.40000
• LogP: 6.74570
• Storage Temp.: room temp
• Solubility.: H2O: soluble10mg/mL, clear, colorless
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 20
• Exact Mass: 407.31644595
• Heavy Atom Count: 27
• Complexity: 363

Purity/Quality:

99% ^*data from raw suppliers

Miltefosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C
• Recent ClinicalTrials: The Association of Miltefosine and Pentoxifylline to Treat Mucosal and Cutaneous Leishmaniasis: A Clinical Trial in Brazil
• Recent EU Clinical Trials: Efficacy and safety of Miltefosine in antihistamine resistant chronic urticaria
• Description: Miltefosin, 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.
• Uses: A phospholipid drug with antineoplastic and antiprotozoal/antifungal properties, also acts as an Akt inhibitor, and under investigation as a potential therapy against HIV infection.
• Clinical Use: Visceral leishmaniasis Cutaneous leishmaniasis

Technology Process of Miltefosine

There total 16 articles about Miltefosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

1-Hexadecanol (36653-82-4,124-29-8) + 2-(((2-cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)-N,N,N-trimethylethan-1-aminium tetraphenylborate → hexadecylphosphocholine (58066-85-6)

Guidance literature:

1-Hexadecanol; 2-(((2-cyanoethoxy)(diisopropylamino)phosphaneyl)oxy)-N,N,N-trimethylethan-1-aminium tetraphenylborate; With 1H-tetrazole; In acetonitrile; at 25 ℃; for 0.5h; Inert atmosphere;

With tert.-butylhydroperoxide; In acetonitrile;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; Reagent/catalyst; Inert atmosphere;

DOI:10.1039/c9ob02582k

Reference yield: 81.0%

2-bromoethyl hexadecyl hydrogen phosphate (72358-41-9) + trimethylamine (75-50-3) → hexadecylphosphocholine (58066-85-6)

Guidance literature:

In chloroform; water; isopropyl alcohol; acetonitrile; at 70 ℃;

DOI:10.1007/s11095-020-02830-y

Reference yield: 80.0%

hexadecyl methyl 2-bromoethylphosphate + trimethylamine (75-50-3) → hexadecylphosphocholine (58066-85-6)

Guidance literature:

In dichloromethane; acetonitrile; at 20 ℃;

DOI:10.1016/S0009-3084(00)00224-3

upstream raw materials:

2-bromoethyl hexadecyl hydrogen phosphate

trimethylamine

2-hexadecyloxy-[1,3,2]dioxaphospholane 2-oxide

1-Hexadecanol

Downstream raw materials:

4-azido-2,3,5,6-tetrafluorobenzoic acid

Refernces

• 1、 Patil, Niteen B.,Atapalkar, Ranjit S.,Chavan, Subhash P.,Kulkarni, Amol A.. "Multi-Step Synthesis of Miltefosine: Integration of Flow Chemistry with Continuous Mechanochemistry". supporting information. p. 17695 - 17699. Retrieved 2021/10/29.
• 2、 Xu, Lianyan L.,Berg, Lawrence J.,Jamin Keith,Townsend, Steven D.. "An effective reagent to functionalize alcohols with phosphocholine". supporting information. p. 767 - 770. Retrieved 2020/02/11.