Clobetasol propionate Chemical Properties

Melting point:

195.5-1970C

alpha 

D +103.8° (c = 1.04 in dioxane)

Boiling point:

569.0±50.0 °C(Predicted)

Density 

1.1653 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Practically insoluble in water, freely soluble in acetone, sparingly soluble in ethanol (96 per cent).

pka

12.88±0.70(Predicted)

InChI

InChI=1/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/s3

InChIKey

CBGUOGMQLZIXBE-XGQKBEPLSA-N

SMILES

O([C@@]1([C@H](C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C)C(=O)CCl)C(=O)CC |&1:1,2,4,6,16,18,20,23,r|

CAS DataBase Reference

25122-46-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-62-53-48/20/21-61

Safety Statements 

26-36-45-36/37-53

WGK Germany 

2

RTECS 

TU3725000

HS Code 

29372290

Clobetasol propionate Usage And Synthesis

Mechanism of Action

Clobetasol Propionate is the propionate salt form of clobetasol, a topical synthetic corticosteroid with anti-inflammatory, anti-pruritic, and vasoconstrictive properties. Clobetasol propionate exerts its effect by binding to cytoplasmic glucocorticoid receptors and subsequently activates glucocorticoid receptor mediated gene expression. This results in the synthesis of certain anti-inflammatory proteins, while inhibiting the synthesis of certain inflammatory mediators. Specifically, clobetasol propionate appears to induce phospholipase A2 inhibitory proteins, thereby controlling the release of the inflammatory precursor arachidonic acid from membrane phospholipids by phospholipase A2.

Indications

Clobetasol propionate is the 17-O-propionate ester of clobetasol and it derives from a clobetasol and a propionic acid. A potent corticosteroid, it is used to treat various skin disorders, including exzema and psoriasis.
Clobetasol propionate was patented in 1968 and came into medical use in 1978. It is available as a generic medication. Clobetasol propionate is used for the treatment of various skin disorders including eczema, herpes labialis, psoriasis, and lichen sclerosus. It is also used to treat several auto-immune diseases, including alopecia areata, lichen planus (auto immune skin nodules), and mycosis fungoides (T-cell skin lymphoma). It is used as first-line treatment for both acute and chronic GVHD of the skin.

Chemical Properties

White or almost white, crystalline powder.

Originator

Dermovate,Glaxo,UK,1973

Uses

Clobetasol-17-propionate is a topical corticosteroid belonging to the group-D (hydrocortisone-q-butyrate) type of steroids.

Uses

For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.

Uses

Topical corticosteroid. Glucocorticoid; anti-inflammatory.

Clobetasol propionate (Cormax, Temovate, Embeline, Olux) is one of the most potent of the currently available agents and is indicated for short-term treatment of inflammatory or hyperplastic disorders. It is a synthetic fluorinated corticosteroid. It may cause a more rapid or prolonged response than other topical corticosteroids. It is recommended that clobetasol have a maximum application of 60 g/week for no longer than 14 days without occlusion and that it should not be used in children below age 12.

Definition

ChEBI: The 17-O-propionate ester of clobetasol. A potent corticosteroid, it is used to treat various skin disorders, including exzema and psoriasis.

Indications

Clobetasol propionate (Cormax, Temovate, Embeline, Olux) is one of the most potent of the currently available agents and is indicated for short-term treatment of inflammatory or hyperplastic disorders. It is a synthetic fluorinated corticosteroid. It may cause a more rapid or prolonged response than other topical corticosteroids. It is recommended that clobetasol have a maximum application of 60 g/week for no longer than 14 days without occlusion and that it should not be used in children below age 12.

Manufacturing Process

A solution of betamethasone 21-methanesulfonate (4 g) in dimethylformamide (25 ml) was treated with lithium chloride (4 g) and the mixture heated on the steam bath for 30 minutes. Dilution with water gave the crude product which was recrystallized to afford the title compound, MP 226°C.
Clobetasol is usually converted to the propionate as the useful form by reaction with propionic anhydride.

brand name

Clobex (Galderma); Clobex (Galderma); Embeline (Healthpoint); Olux (Connetics); Temovate (Altana).

Therapeutic Function

Corticosteroid, Antiinflammatory

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