Fingolimod

Base Information

• Chemical Name: Fingolimod
• CAS No.: 162359-55-9
• Molecular Formula: C19H33NO2
• Molecular Weight: 307.477
• UNII: 3QN8BYN5QF
• DSSTox Substance ID: DTXSID40167363
• Nikkaji Number: J729.665G
• Wikipedia: Fingolimod
• Wikidata: Q425137
• NCI Thesaurus Code: C74202
• RXCUI: 1012892
• Pharos Ligand ID: 7TJCA8256R3B
• Metabolomics Workbench ID: 62614
• ChEMBL ID: CHEMBL314854
• Mol file: 162359-55-9.mol

Synonyms:2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride;fingolimod;fingolimod hydrochloride;FTY 720;FTY-720;FTY720;Gilenia;gilenya

Chemical Property of Fingolimod

Chemical Property:

• Melting Point: 103-105°
• Boiling Point: 479.5 °C at 760 mmHg
• PKA: 12.20±0.20(Predicted)
• Flash Point: 243.8 °C
• PSA: 66.48000
• Density: 1.016g/cm³
• LogP: 3.90460
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform (Very Slightly, Heated), DMSO (Slightly, Heated), Methanol (Slightly,
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 307.251129295
• Heavy Atom Count: 22
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

Fingolimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Multiple Sclerosis Agents
• Canonical SMILES: CCCCCCCCC1=CC=C(C=C1)CCC(CO)(CO)N
• Recent ClinicalTrials: A Study To Evaluate Safety And Efficacy Of Ocrelizumab In Comparison With Fingolimod In Children And Adolescents With Relapsing-Remitting Multiple Sclerosis
• Recent EU Clinical Trials: Multi-center, Randomized, Double-blind, Parallel-group, Double-dummy, Active-controlled, Comparative Study to Evaluate the Efficacy, Safety, Pharmacokinetics, and Pharmacodynamics of Ponesimod Versus Fingolimod During 108 Weeks of Treatment in Pediatric Participants, 10 to <18 Years Old, with Relapsing-remitting Multiple Sclerosis
• Recent NIPH Clinical Trials: Investigation for immune response against JC virus in Multiple Sclerosis patients on treatment with fingolimod
• Uses: Prophylaxis of organ rejection in patients receiving allogenic renal transplants (sphingosine-1-phosphate receptor). Fingolimod is a novel immune modulator that prolongs allograft transplant survival in numerous models by inhibiting lymphocyte emigration from lymphoid organs.
• Clinical Use: Sphingosine 1-phosphate receptor modulator:Treatment of highly active relapsing-remitting multiple sclerosis
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: possible increased risk of bradycardia with amiodarone, disopyramide and dronedarone. Antifungals: concentration increased by ketoconazole. Beta-blockers: possibly increased risk of bradycardia. Calcium channel blockers: possible increased risk of bradycardia with diltiazem and verapamil.

Technology Process of Fingolimod

There total 70 articles about Fingolimod 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: 96.0%

5-(tert-butyloxycarbonylamino)-2,2-dimethyl-5-(4-octylphenethyl)-1,3-dioxane (885605-36-7) → fingolimod (162359-55-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1055/s-2006-926342

Reference yield: 95.0%

C33H59NO2Si → fingolimod (162359-55-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1038/nchem.2367

Reference yield: 92.1%

C22H33NO4 → fingolimod (162359-55-9)

Guidance literature:

C₂₂H₃₃NO₄; With 5%-palladium/activated carbon; hydrogen; In ethanol; at 40 - 45 ℃; for 5h; under 1500.15 - 2250.23 Torr; Autoclave; Inert atmosphere;

With hydrogenchloride; In ethanol; water; at 60 - 65 ℃; for 4h; Reagent/catalyst; Temperature; Solvent;

upstream raw materials:

2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate

2-nitro-2-[2-(4-octyl-phenyl)ethyl]propane-1,3-diol

5-(tert-butyloxycarbonylamino)-2,2-dimethyl-5-(4-octylphenethyl)-1,3-dioxane

tert-butyl 2,2-dimethyl-5-[(4-octylphenyl)ethynyl]-1,3-dioxan-5-ylcarbamate

Downstream raw materials:

2-amino-2-(2-(4-octylphenyl) ethyl) propane-1,3-diol lactic acid salt

fingolimod besylate

fingolimod tosylate

phosphoric acid mono-[(S)-2-amino-2-hydroxymethyl-4-(2-iodo-4-octylphenyl)butyl] ester

Refernces

• 1、 Askey, Hannah E.,Grayson, James D.,Tibbetts, Joshua D.,Turner-Dore, Jacob C.,Holmes, Jake M.,Kociok-Kohn, Gabriele,Wrigley, Gail L.,Cresswell, Alexander J.. "Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines". supporting information. p. 15936 - 15945. Retrieved 2021/10/12.
• 2、 Bai, Songlin,Gao, Yadong,Jiang, Chao,Liu, Xiaolei,Qi, Xiangbing,Wang, Jing,Wu, Qingcui,Yang, Chao. "Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes". supporting information. p. 675 - 688. Retrieved 2020/03/11.