Eflornithine

Base Information

• Chemical Name: Eflornithine
• CAS No.: 70052-12-9
• Deprecated CAS: 67037-37-0
• Molecular Formula: C6H12F2N2O2
• Molecular Weight: 182.17
• NSC Number: 337250
• UNII: ZQN1G5V6SR
• DSSTox Substance ID: DTXSID3020467
• Nikkaji Number: J65.668B
• Wikipedia: Eflornithine
• Wikidata: Q424751
• NCI Thesaurus Code: C226
• RXCUI: 569
• Pharos Ligand ID: QLF2GYA564KZ
• Metabolomics Workbench ID: 52298
• ChEMBL ID: CHEMBL830
• Mol file: 70052-12-9.mol

Synonyms:alpha Difluoromethyl Ornithine;alpha Difluoromethylornithine;alpha-Difluoromethyl Ornithine;alpha-Difluoromethylornithine;Difluoromethylornithine;DL alpha Difluoromethylornithine;DL-alpha-Difluoromethylornithine;Eflornithine;Eflornithine Hydrochloride;Eflornithine Monohydrochloride, Monohydrate;MDL 71,782 A;MDL-71,782 A;MDL71,782 A;Ornidyl;Ornithine, alpha-Difluoromethyl;RMI 71782;Vaniqa

Chemical Property of Eflornithine

Chemical Property:

• Vapor Pressure: 9.72E-06mmHg at 25°C
• Melting Point: 138 °C
• Refractive Index: 1.462
• Boiling Point: 347 °C at 760 mmHg
• PKA: 1.22±0.44(Predicted)
• Flash Point: 163.7 °C
• PSA: 89.34000
• Density: 1.293g/cm³
• LogP: 1.17310
• Storage Temp.: Store at 0°C
• Solubility.: H2O: >10 mg/mL, soluble
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 182.08668395
• Heavy Atom Count: 12
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

DFMO ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(C(F)F)(C(=O)O)N)CN
• Recent ClinicalTrials: Eflornithine (DFMO) and Etoposide for Relapsed/Refractory Neuroblastoma
• Recent EU Clinical Trials: A Phase 3, Randomized, Open-Label Study To Evaluate the Efficacy and Safety of Eflornithine with Lomustine Compared to Lomustine Alone in Patients with Anaplastic Astrocytoma That Progress/Recur After Irradiation and Adjuvant Temozolomide Chemotherapy
• Uses: DL-α-Difluoromethylornithine hydrochloride hydrate has been used to reduce the effects of arginine on cell proliferation. It has also been used to investigate the effect of bisphenol A (BPA) on the migration of an established ovine trophectoderm (oTr1) cell line.

Technology Process of Eflornithine

There total 6 articles about Eflornithine 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: 88.2%

ethyl 2,5-diamino-2-(difluoromethyl)pentanoate dihydrochloride → eflornithine (70052-12-9,66640-93-5)

Guidance literature:

With hydrogenchloride; at 110 ℃;

DOI:10.1016/j.tetlet.2005.02.146

Reference yield:

dibenzylidene ornithine ethyl ester → dibenzylidene α-difluoromethylornithine ethyl ester + eflornithine (70052-12-9,66640-93-5)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; dichloromethane;

Reference yield:

ethyl 2-(diphenylmethylene)amino-2-difluoromethyl-4-cyanobutanoate (501011-48-9) → eflornithine (70052-12-9,66640-93-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.3 percent / aq. HCl; MTBE / 1.5 h / 20 °C

2: 76.2 percent / hydrogen; concd. HCl / Pt/C / ethanol / 63 h / 4912.91 Torr

3: 88.2 percent / concd. HCl / 110 °C

With hydrogenchloride; tert-butyl methyl ether; hydrogen; platinum on activated charcoal; In ethanol;

DOI:10.1016/j.tetlet.2005.02.146

upstream raw materials:

ethyl 2-amino-2-difluoromethyl-4-cyanobutanoate

ethyl 2-(diphenylmethylene)amino-2-difluoromethyl-4-cyanobutanoate

Downstream raw materials:

C₂₂H₂₀F₄N₄O₁₀

C₁₄H₁₆F₃N₃O₆

C₂₂H₂₂F₂N₄O₁₀

C₁₄H₁₇F₂N₃O₆

Refernces

• 1、 -. "Method of inhibiting the growth of protozoa". . . Retrieved 2008/06/13.
• 2、 -. "Method of inhibiting algae". . . Retrieved 2008/06/13.