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

Originator

Haldrone,Lilly,US,1961

Uses

Different sources of media describe the Uses of 1597-82-6 differently. You can refer to the following data:
1. Paramethasone Acetate, is a derivative of Dexamethasone (D298800), a potent synthetic member of the glucocorticoid class of steroid drugs that has anti-inflammatory and immunosuppressant properties.
2. Glucocorticoid.

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.

Brand name

Haldrone (Lilly).

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

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

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.