Halcinonide Chemical Properties

Melting point:

264-265° (dec)

alpha 

D25 +155° (CHCl3)

Boiling point:

564.3±50.0 °C(Predicted)

Density 

1.1567 (estimate)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

13.19±0.70(Predicted)

color 

White to Off-White

InChIKey

MUQNGPZZQDCDFT-JNQJZLCISA-N

SMILES

O1[C@]2([H])C[C@]3([H])[C@@](C)([C@]2(C(CCl)=O)OC1(C)C)C[C@H](O)[C@]1(F)[C@]2(C)C(=CC(=O)CC2)CC[C@@]31[H]

CAS DataBase Reference

3093-35-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

63

Safety Statements 

36

WGK Germany 

3

RTECS 

TU5010200

HS Code 

2937220000

Toxicity

LD50 i.p. in mice: 150 mg/kg (Millonig, Yiakas)

MSDS

• Language:English Provider:(11b,16a)-21-Chloro-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregn-4-ene-3,20-dione
• Language:English Provider:SigmaAldrich

Halcinonide Usage And Synthesis

Outline

Halcinonide is an efficient synthetic fluorine and chlorine corticosteroid, the effect of it is similar to fludrocortisone . It has strong anti-inflammatory, anti-allergic, anti-itching, inhibiting proliferation of immune effects, topical application can reduce the permeability of the capillary wall and cell membrane,and reduce the inflammatory exudate, and inhibit histamine and other inflammatory mediators formation and release.it is clinically used for subacute or chronic non-infectious skin diseases such as psoriasis, eczema, neurodermatitis, contact dermatitis, seborrheic dermatitis (non-face), atopic dermatitis, flat moss and discoid lupus erythematosus and the like which are hormone therapy ineffective .

Physical and Chemical Properties

White or off-white crystalline powder, odorless. Almost insoluble in water, slightly soluble in ethanol or methanol, soluble in acetone and chloroform. Sealed.

Pharmacological effects

This drug is a potent synthetic glucocorticoid ,its action is similar to fludrocortisone. It has strong anti-inflammatory, anti-allergic, anti-itching, inhibit proliferation of immune and other effects, topical application are unlikely to cause systemic adverse reactions. The drug has the same effect of inhibiting the proliferation of granulation tissue as dexamethasone ,it is stronger than hydrocortisone. The drug is not substantially absorbed in external skin, it has no irritating effect on the body. The extent of absorption of topical application is hugely different among anatomic sites: forearm 1%, 4% of the scalp, forehead, 7%, 36% of the scrotum, the greatest penetration is in the groin, armpits and face. The drug is mainly metabolized in the liver, it is mostly excreted by the kidneys, and less by biliary excretion.
The above information is edited by the chemicalbook of Tian Ye.

Indications

The drug is suitable for treatment of contact dermatitis, atopic dermatitis, lichen,the small size of psoriasis, lichen, heat rash, genital atrophic lichen sclerosus, non-parasitic prurigo, ring granuloma, discoid lupus erythematosus, non-facial seborrheic dermatitis, mycosis fungoides pruritus symptomatic .It is also used for the treatment of insect bites, parasitic prurigo through specific treatment. It has a good effect on the treatment of psoriasis .

Adverse reactions

1. There are a small number of patients whose applicator parts of the skin occurs burning, stinging, itching temporary, long-term use can occur telangiectasia skin (especially face), skin atrophy, stretch marks (teenagers prone), fragile skin, hirsutism, folliculitis, milia, skin bleaching, delayed ulcer healing, packet method in skin folds easily causes fungal infection.
2. When it is much absorbed through the skin, it can cause systemic adverse reactions.

Contraindications

1.Patients who are allergic to this drug and adrenal corticosteroids are banned.
2. The primary skin diseases , exudative dermatitis, ulcerative lesions, acne, rosacea caused by bacteria, fungi, viruses and parasites are banned.
3. It is forbidden using in the eyelid portion (cause a risk of glaucoma).

Precautions

1. The large area of large quantities of drugs or medication packet mode allow more amount of the drug being absorbed through the skin, which causes systemic reactions, especially in young children and infants, it can cause reversible Cushing's syndrome and growth retardation, sudden withdrawal can cause acute adrenal insufficiency.
2. When the local intolerance phenomena occurs,the drug should be stopped and the reason should be found.
3. It should be paid attention that drug staying in the skin folds and diaper can be absorbed into the body.

Specification

Ointments, creams, solutions: 0.1%.

Uses

Cortical hormone drugs for the treatment of psoriasis and eczema dermatitis .

Originator

Halog,Squibb,US,1974

Uses

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.

Uses

Anti-inflammatory (topical).

Definition

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

Indications

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

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.

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