Flunisolide

Base Information

• Chemical Name: Flunisolide
• CAS No.: 3385-03-3
• Molecular Formula: C₂₄H₃₁FO₆
• Molecular Weight: 434.505
• European Community (EC) Number: 222-193-2
• UNII: 78M02AA8KF
• DSSTox Substance ID: DTXSID1045534
• Nikkaji Number: J3.402I
• Wikipedia: Flunisolide
• Wikidata: Q3746835
• NCI Thesaurus Code: C29054,C132268
• RXCUI: 1546428
• Pharos Ligand ID: YYW5APNQR5D8
• Metabolomics Workbench ID: 42588
• ChEMBL ID: CHEMBL1512
• Mol file: 3385-03-3.mol

Synonyms:6 alpha-fluorodihydroxy-16 alpha,17 alpha-isopropylidenedioxy-1,4-pregnadiene-3,20- dione;6alpha-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16, 17-acetal with acetone;AeroBid;Aerospan;Apo-Flunisolide;flunisolide;flunisolide 21-acetate;flunisolide acetate;flunisolide anhydrous;flunisolide hemihydrate;flunisolide hemihydrate, (6alpha,11beta,16alpha)-isomer;flunisolide HFA;flunisolide hydrofluoroalkane;flunisolide, (6beta,11beta,16alpha)-isomer;Inhacort;Nasalide;Nasarel;ratio-Flunisolide;Rhinalar;RS-1320;RS-3999;RS1320;Syntaris

Chemical Property of Flunisolide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 5.87E-16mmHg at 25°C
• Melting Point: 237-240°C (dec.)
• Boiling Point: 581.8 °C at 760 mmHg
• PKA: 12.87±0.10(Predicted)
• Flash Point: 305.7 °C
• PSA: 93.06000
• Density: 1.33 g/cm³
• LogP: 2.27470
• Storage Temp.: Refrigerator
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 434.21046687
• Heavy Atom Count: 31
• Complexity: 910

Purity/Quality:

99%, ^*data from raw suppliers

Flunisolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OC2CC3C4CC(C5=CC(=O)C=CC5(C4C(CC3(C2(O1)C(=O)CO)C)O)C)F)C
• Isomeric SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)C[C@@H](C5=CC(=O)C=C[C@]35C)F)O
• Recent ClinicalTrials: Validation Of Preference Module Of Experience With Allergic Rhinitis Nasal Sprays Questionnaire (EARNS-Q)
• Recent EU Clinical Trials: AEROSOLIC TREATMENT OF ACUTE AND RECURRENT RHINOSINUSITIS DURING INTERCRITICAL STAGES : SINGLE BLIND CLINICAL STUDY, N-ACETYLCISTEIN VS AMBROXOL, ASSOCIATED WITH CORTISONE THERAPY
• Uses: Synthetic fluorinated corticosteroid related to Prednisolone (P703740). Antiasthmatic.
• Therapeutic Function: Antiinflammatory
• Clinical Use: Flunisolide is an acetone ketal (acetonide) with a 6α-fluoro group and a free C-21 hydroxyl group. The acetonide decreases mineralocorticoid activity, and the 6α-fluoro group increases glucocorticoid activity. It is not a prodrug, because it has the free hydroxyl group at C-21. Flunisolide has approximately 20% of the receptor affinity as budesonide, and approximately 40% of the inhaled dose is systemically bioavailable.

Technology Process of Flunisolide

There total 11 articles about Flunisolide 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-(acetyloxy)-6α-fluoro-11β-hydroxy-16α,17-<(1-methylethylidene)bis(oxy)>pregna-1,4-diene-3,20-dione (4533-89-5) → flunisolide (3385-03-3,3870-63-1,79284-83-6)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; at -10 - 0 ℃; Inert atmosphere;

Reference yield:

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (37413-91-5) → flunisolide (3385-03-3,3870-63-1,79284-83-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: formic acid; potassium permanganate / acetone; water / 0.5 h / -7 - -3 °C / Industrial scale

2.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; perchloric acid / water; tetrahydrofuran / 1 h / -8 - -4 °C / Industrial scale

3.1: chromium(III) chloride hexahydrate; zinc; mercaptoacetic acid / N,N-dimethyl-formamide; dimethyl sulfoxide / 1 h / -10 °C / Inert atmosphere; Industrial scale

4.1: perchloric acid / 1.5 h / 26 - 35 °C / Inert atmosphere

5.1: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 5 °C / Inert atmosphere

6.1: methanesulfonic acid / 1 h / 65 - 80 °C

6.2: 12 h / -5 - 15 °C

7.1: sodium hydroxide / methanol; dichloromethane / -10 - 0 °C / Inert atmosphere

With potassium permanganate; formic acid; perchloric acid; methanesulfonic acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; chromium(III) chloride hexahydrate; mercaptoacetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

Reference yield:

11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 21-acetate (25092-25-5) → flunisolide (3385-03-3,3870-63-1,79284-83-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 5 °C / Inert atmosphere

2.1: methanesulfonic acid / 1 h / 65 - 80 °C

2.2: 12 h / -5 - 15 °C

3.1: sodium hydroxide / methanol; dichloromethane / -10 - 0 °C / Inert atmosphere

With methanesulfonic acid; sodium hydroxide; In methanol; dichloromethane;

upstream raw materials:

11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-acetonide 21-acetate

desonide

21-(acetyloxy)-6α-fluoro-11β-hydroxy-16α,17-<(1-methylethylidene)bis(oxy)>pregna-1,4-diene-3,20-dione

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Downstream raw materials:

flurandrenolide

Refernces

• 1、 -. "NOVEL PROCESS FOR PREPARATION OF GLUCOCORTICOID STEROIDS". . . Retrieved 2016/08/23.
• 2、 -. "Pharmaceutical composition using a mixture of propellant gases for a metered dose inhaler". . . Retrieved 2008/06/13.