Corticosterone, 9-fluoro-17-hydroxy-, 21-acetate

Base Information

• Chemical Name: Corticosterone, 9-fluoro-17-hydroxy-, 21-acetate
• CAS No.: 514-36-3
• Molecular Formula: C23H31FO6
• Molecular Weight: 422.494
• Hs Code.: 2937220000
• European Community (EC) Number: 208-180-4
• NSC Number: 757031
• NCI Thesaurus Code: C1103
• RXCUI: 165516
• Mol file: 514-36-3.mol

Synonyms:9 alpha-fluorocortisol acetate;9-fluoro-11beta,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate;Cortineff;Florinef;fludrocortisone 21-acetate;fludrocortisone acetate;fluorocortisol acetate

Chemical Property of Corticosterone, 9-fluoro-17-hydroxy-, 21-acetate

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 1.27E-15mmHg at 25°C
• Melting Point: 233-234 °C
• Refractive Index: 1.563
• Boiling Point: 575.1 °C at 760 mmHg
• PKA: 12.06±0.70(Predicted)
• Flash Point: 301.6 °C
• PSA: 100.90000
• Density: 1.3 g/cm³
• LogP: 2.44450
• Storage Temp.: -20°C Freezer
• Solubility.: Practically insoluble in water, sparingly soluble in anhydrous ethanol.
• Water Solubility.: 54mg/L(25 oC)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 422.21046687
• Heavy Atom Count: 30
• Complexity: 838

Purity/Quality:

99%, ^*data from raw suppliers

Fludrocortisone acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63
• Safety Statements: 22-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1(CCC2C1(CC(C3(C2CCC4=CC(=O)CCC43C)F)O)C)O
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CCC2[C@@]1(C[C@@H]([C@]3(C2CCC4=CC(=O)CC[C@@]43C)F)O)C)O
• Recent EU Clinical Trials: The effect of fludrocortisone on emotional information processing in healthy volunteers
• Description: Fludrocortisone acetate is the acetate form of the synthetic corticosteroid fludrocortisone, which is a mineralocorticoid receptor agonist. Fludrocortisone acetate (0.1-5 μg/animal) promotes sodium retention in rats in a dose-dependent manner with 37% of sodium excreted compared with control when used at a dose of 5 μg/animal. Formulations containing fludrocortisone acetate have been used in the treatment of Addison’s disease.
• Clinical Use: Replacement therapy in adrenal insufficiency
• Drug interactions: Potentially hazardous interactions with other drugs Aldesleukin: avoid concomitant use. Antibacterials: metabolism accelerated by rifamycins; metabolism possibly inhibited by erythromycin; possibly reduce isoniazid concentration. Anticoagulants: efficacy of coumarins and phenindione may be altered. Antiepileptics: metabolism accelerated by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone. Antifungals: increased risk of hypokalaemia with amphotericin - avoid; metabolism possibly inhibited by itraconazole and ketoconazole. Antivirals: concentration possibly increased by ritonavir. Cobicistat: concentration of fludrocortisone increased. Vaccines: high dose corticosteroids can impair immune response to vaccines - avoid concomitant use with live vaccines

Technology Process of Corticosterone, 9-fluoro-17-hydroxy-, 21-acetate

There total 9 articles about Corticosterone, 9-fluoro-17-hydroxy-, 21-acetate 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: 57.4%

9β,11β-epoxy-17α-hydroxypregna-4‐ene-3,20-dione-21-acetate (4383-30-6) → fludrocortisone acetate (514-36-3)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; at 0 - 10 ℃; for 2h; Reagent/catalyst; Solvent;

Reference yield:

21-acetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione (4383-30-6,96843-90-2) → fludrocortisone acetate (514-36-3)

Guidance literature:

With hydrogen fluoride;

DOI:10.1021/ja01562a030 DOI:10.1021/ja01600a040

Reference yield:

Epicortisol (566-35-8) → fludrocortisone acetate (514-36-3)

Guidance literature:

Multi-step reaction with 5 steps

1: dann mit Methansulfonylchlorid

2: sodium acetate; acetic acid

3: HClO₄; aqueous dioxane

4: dioxane; potassium acetate; ethanol

5: HF

With 1,4-dioxane; perchloric acid; ethanol; hydrogen fluoride; potassium acetate; sodium acetate; acetic acid;

DOI:10.1021/ja01562a030

upstream raw materials:

21-acetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione

chloroform

hydrogen fluoride

Epicortisol

Downstream raw materials:

9α-Fluor-11β-hydroxy-3,17-dioxo-androsten-4

9α-fluorocortisone

9-fluoro-11β,17-dihydroxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione

9-fluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione