Fluprednisolone

Base Information

• Chemical Name: Fluprednisolone
• CAS No.: 53-34-9
• Molecular Formula: C21H27FO5
• Molecular Weight: 378.441
• European Community (EC) Number: 200-170-8
• NSC Number: 47439
• UNII: 9H05937G3X
• DSSTox Substance ID: DTXSID5046067
• Nikkaji Number: J4.143B
• Wikipedia: Fluprednisolone
• Wikidata: Q732234
• NCI Thesaurus Code: C65730
• Pharos Ligand ID: AMGKWJSSGBJX
• Metabolomics Workbench ID: 152366
• ChEMBL ID: CHEMBL1200774
• Mol file: 53-34-9.mol

Synonyms:Fluprednisolone

Chemical Property of Fluprednisolone

Chemical Property:

• Vapor Pressure: 1.77E-15mmHg at 25°C
• Melting Point: 208-213°
• Refractive Index: 1.597
• Boiling Point: 572.3 °C at 760 mmHg
• Flash Point: 299.9 °C
• PSA: 94.83000
• Density: 1.35 g/cm³
• LogP: 1.50560
• Storage Temp.: Refrigerator
• Solubility.: Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 174.2mg/L(20 oC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 378.18425212
• Heavy Atom Count: 27
• Complexity: 760

Purity/Quality:

99%, ^*data from raw suppliers

6α-Fluprednisolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3C(C1CCC2(C(=O)CO)O)CC(C4=CC(=O)C=CC34C)F)O
• Isomeric SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@]2(C(=O)CO)O)C[C@@H](C4=CC(=O)C=C[C@]34C)F)O
• Description: Fluprednisolone (6α-fluoro-11β,17,21-trihydroxy-pregna-1,4-diene-3,20-dione) is the 16-desmethyl analogue of paramethasone. Its activity is similar to that of paramethasone, and it has approximately 2.5 times the antirheumatic potency of prednisolone. With doses of 2 to 7 mg, evidence of salt and water retention has not been noted. The therapeutic index, however, probably is the same or only a little greater than that for prednisolone. Because no new adverse reactions have been noted during the administration of this drug on a short-term basis, it seems that a 6α-fluoro group does not deleteriously affect the activity of prednisolone (49,75).
• Uses: 6α-Fluprednisolone is an anti-inflammatory corticosteroid metabolite. Glucocorticoid.

Technology Process of Fluprednisolone

There total 5 articles about Fluprednisolone 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:

21-acetoxy-6α-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione (1058-55-5) → fluprednisolone (53-34-9)

Guidance literature:

With septomyxa affinin;

Reference yield:

21-acetoxy-6β-fluoro-5,11β,17-trihydroxy-5α-pregnane-3,20-dione (913-49-5) → fluprednisolone (53-34-9)

Guidance literature:

Multi-step reaction with 3 steps

1: aqueous acetic acid

2: HCl

3: septomyxa affinin

With hydrogenchloride; septomyxa affinin; acetic acid;

Reference yield:

21-acetoxy-6β-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione (986-37-8) → fluprednisolone (53-34-9)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl

2: septomyxa affinin

With hydrogenchloride; septomyxa affinin;

upstream raw materials:

21-acetoxy-6α-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione

21-acetoxy-6β-fluoro-5,11β,17-trihydroxy-5α-pregnane-3,20-dione

21-acetoxy-6β-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione

Refernces

• 1、 -. "Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid". . . Retrieved 2008/06/13.
• 2、 -. "Amine containing ester prodrugs of corticosteroids". . . Retrieved 2008/06/13.