1597-82-6

Basic information

• Product Name: PARAMETHASONE ACETATE (200 MG)
• Synonyms: 16-alpha-methyl-6-alpha-fluoro-prednisolone-21-acetate;21-acetyl-6-alpha-fluoro-16-alpha-methylprednisolone;6-alpha-fluoro-16-alpha-methylprednisolone21-acetate;alondra;cortidene;21-Acetoxy-6a-fluoro-11b,17-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione;21-Acetyl-6a-fluoro-16a-methylprednisolone;6a-Fluoro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione 21-acetate
• CAS NO: 1597-82-6
• Molecular Formula: C₂₄H₃₁FO₆
• Molecular Weight: 434.4977432
• EINECS: 216-486-4
• Mol File: 1597-82-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 228-241° (dec)
• Boiling Point: 584.2 °C at 760 mmHg
• Flash Point: 307.1 °C
• Appearance: /
• Density: 1.1517 (estimate)
• Vapor Pressure: 4.42E-16mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.29±0.70(Predicted)
• CAS DataBase Reference: PARAMETHASONE ACETATE (200 MG)(CAS DataBase Reference)
• NIST Chemistry Reference: PARAMETHASONE ACETATE (200 MG)(1597-82-6)
• EPA Substance Registry System: PARAMETHASONE ACETATE (200 MG)(1597-82-6)

Safety Data

• Hazardous Substances Data: 1597-82-6(Hazardous Substances Data)

Usage

Description

PARAMETHASONE ACETATE (200 MG) is a potent synthetic glucocorticoid, a derivative of Dexamethasone, which possesses anti-inflammatory and immunosuppressant properties. It is a steroid drug that is widely used in the medical field for its therapeutic effects.

Uses

Used in Pharmaceutical Industry:
PARAMETHASONE ACETATE (200 MG) is used as an anti-inflammatory agent for reducing inflammation and alleviating the symptoms of various inflammatory conditions.
PARAMETHASONE ACETATE (200 MG) is used as an immunosuppressant for suppressing the immune system and preventing organ transplant rejection or treating autoimmune diseases.
Used in Healthcare:
PARAMETHASONE ACETATE (200 MG) is used as a treatment for various skin conditions, such as eczema, dermatitis, and psoriasis, due to its anti-inflammatory and immunosuppressant properties.
PARAMETHASONE ACETATE (200 MG) is used as a treatment for allergic reactions, such as asthma, allergic rhinitis, and urticaria, to reduce inflammation and alleviate symptoms.
Used in Veterinary Medicine:
PARAMETHASONE ACETATE (200 MG) is used as a medication for veterinary purposes, such as treating inflammatory and allergic conditions in animals.
Brand name: Haldrone (Lilly).

Originator

Haldrone,Lilly,US,1961

Manufacturing Process

A solution of 0.144 g of the 3-ethylene glycol ketal of 5α,11β,17α,21 tetrahydroxy-6β-fluoro-16α-methylallopregnane-3,20-dione-21 acetate in 12 ml of chloroform and 0.1 ml of absolute alcohol was cooled to -10°C in an icesalt bath and a stream of anhydrous hydrochloric acid was gently bubbled through the solution for 2.5 hours while the temperature was maintained between -5°C and -15°C. The solution was then diluted with 25 ml of chloroform, washed with dilute sodium bicarbonate and water, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure at 60°C or less to give 6α-fluoro-11β,17α,21-trihydroxy-16α-methyl-4-pregnene3,20-dione 21-acetate.

Therapeutic Function

Glucocorticoid

Safety Profile

Poison by intraperitoneal route. An experimental teratogen. When heated to decomposition it emits toxic fumes of Fí.

InChI:InChI=1/C24H31FO6/c1-12-7-16-15-9-18(25)17-8-14(27)5-6-22(17,3)21(15)19(28)10-23(16,4)24(12,30)20(29)11-31-13(2)26/h5-6,8,12,15-16,18-19,21,28,30H,7,9-11H2,1-4H3/t12-,15+,16+,18+,19+,21-,22+,23+,24+/m1/s1

Synthetic route

21-acetoxy-6α-fluoro-11β,17-dihydroxy-16α-methyl-pregn-4-ene-3,20-dione (1524-93-2) → paramethasone acetate (1597-82-6)

Conditions	Yield
With selenium(IV) oxide

21-acetoxy-3,3-ethanediyldioxy-6β-fluoro-16α-methyl-5α-pregn-17(20)t-ene-5,11β-diol (3862-45-1) → paramethasone acetate (1597-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4-methyl-morpholine; H2O2; OsO4 / anschliessend mit HCl in CHCl3 und Aethanol 2: SeO2 View Scheme

chromium chloride hexahydrate + 9α-Bromo-6α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate → paramethasone acetate (1597-82-6)

Conditions	Yield
With zinc In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone

paramethasone acetate (1597-82-6) → 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-21-acetoxypregna-1,4-diene-3,20-dione (2823-42-9)

Conditions	Yield
ueber mehrere Stufen;

Upstream product

• 1524-93-2 21-acetoxy-6α-fluoro-11β,17-dihydroxy-16α-methyl-pregn-4-ene-3,20-dione 
• 3862-45-1 21-acetoxy-3,3-ethanediyldioxy-6β-fluoro-16α-methyl-5α-pregn-17(20)t-ene-5,11β-diol 
• 1997-73-5 9α-Bromo-6α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate 

Downstream Products

• 2823-42-9 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-21-acetoxypregna-1,4-diene-3,20-dione 

Relevant articles and documents

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Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid

This invention discloses an improved process for the production of corticoids from 17α-hydroxy steroids utilizing peroxymonosulfate.