Halcinonide

Toxicity

Systemic absorption of topical corticosteroids has produced reversible hypothalamicpituitary-adrenal (HPA) axis suppression, manifestations of Cushing’s syndrome, hyperglycemia, and glucosuria in some patients. Conditions which augment systemic absorption include the application of the more potent steroids, use over large surface areas, prolonged use, and the addition of occlusive dressings.

Originator

Halog,Squibb,US,1974

The Uses of Halcinonide

Anti-inflammatory (topical).

The Uses of Halcinonide

2H-Naphth[2'',1'':4,5]indeno[1,2-d][1,3]dioxole Pregn-4-ene-3,20-dione Deriv. is a by-product from the synthesis of 4-Fluorotriamcinolone Acetonide (F598640) an analog of Fluocinolone Acetonide (F455800); a glucocorticoid and anti-inflammatory agent.

Background

Halcinonide is a corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses, and is distributed as a cream and ointment. Halcinonide is marketed under the brand name Halog? by Ranbaxy Laboratories Inc. Research suggests that clobetasol propionate demonstrates superior pharmacologic efficacy in the treatment of psoriasis when compared to halcinonide.

Indications

Indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Indications

Halcinonide (Halog, Halog-E) is a synthetic fluorinated corticosteroid.

Definition

ChEBI: Halcinonide is an organic molecular entity. It has a role as a SMO receptor agonist.

Manufacturing Process

(A) 16α-Hydroxy-9α-fluorohydrocortisone acetonide 27-mesylate: To a solution of 1.5 g of 16α-hydroxy-9α-fluorohydroortisone acetonide in 15 ml of dry pyridine is added at 0°C. 1.5 ml of methane-sulfonyl chloride. After standing in the refrigerator for 2,5 hours, excess methanesulfonyl chloride is destroyed by the addition of a small amount of ice, after which ice-water is added slowly to precipitate the reaction product. After ? hour in the refrigerator the material is filtered off, washed thoroughly with water and dried in vacuo. The resulting crude material after recrystallization from acetone-hexane gives the pure 21-mesylate of the following properties: melting point about 225°C to 227°C (decomposition); [α]D23+112° (c, 0.5 in chloroform).
(B) 21-Chloro-9α-fluoro-δ4-pregnene-11β,16α,17α-triol-3,20-dione16,17- acetonide : A solution of 200 mg of the acetonide 21-mesylate from part (A) and 900 mg of lithium chloride in 25 ml of dimethylformamide is kept at 100°C for 24 hours. The mixture is poured on ice, extracted with chloroform and the chloroform extract washed with water and dried over sodium sulfate. Evaporation of the solvent in vacuo furnishes the crystalline chloride, which after recrystallization from acetone-ethanol has a melting point about 276°C to 277°C.

brand name

Halog (Bristol-Myers Squibb); Halog (Westwood-Squibb).

Therapeutic Function

Topical corticosteroid

General Description

Halcinonide, 21-chloro-9-fluoro-11β-hydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione, was the first chloroGC marketed. Likemany other potent GCs, it is used only topically.

Metabolism

Not Available