Betamethasone 17-valerate Chemical Properties

Melting point:

183-184°

alpha 

D +77° (dioxane)

Boiling point:

598.9±50.0 °C(Predicted)

Density 

1.1174 (estimate)

storage temp. 

2-8°C

solubility 

Practically insoluble in water, freely soluble in acetone and in methylene chloride, soluble in ethanol (96 per cent).

pka

12.90±0.70(Predicted)

color 

White

Merck 

13,1183

BRN 

4240001

InChIKey

SNHRLVCMMWUAJD-SUYDQAKGSA-N

SMILES

[C@]12(C)C[C@@H]([C@]3(F)[C@@]4(C)C=CC(=O)C=C4CC[C@@]3([H])[C@]1([H])C[C@H](C)[C@@]2(C(=O)CO)OC(=O)CCCC)O |&1:0,3,4,6,16,18,21,23,r|

CAS DataBase Reference

2152-44-5(CAS DataBase Reference)

EPA Substance Registry System

.beta.-Methasone 17-valerate (2152-44-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

48

Safety Statements 

22-24/25

RTECS 

TU3835000

HS Code 

2937229000

Toxicity

mouse,LD50,intraperitoneal,632mg/kg (632mg/kg),Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973.

MSDS

• Language:English Provider:1,4-Pregnadiene-11b,17a,21-triol-9a-fluoro-16b-methyl-3,20-dione 17-valerate
• Language:English Provider:SigmaAldrich

Betamethasone 17-valerate Usage And Synthesis

Description

Betamethasone 17-valerate is a synthetic glucocorticoid ester. It is the 17-valerate ester of betamethasone. Betamethasone 17-valerate is often used to treat mild eczema with good efficacy and lower incidence of steroid induced adverse effects due to its lower potency compared to other glucocorticoids. It is available in cream, ointment, lotion, and foam preparations for topical use.

Chemical Properties

White Solid

Originator

Valisone,Schering,US,1967

Uses

Betamethasone 17-Valerate is a glucocorticoid with anti-inflammatory properties and immunosuppressive activity. It is an antiepileptic non-selective phosphodiesterase inhibitor. Topical application of Betamethasone 17-Valerate has been shown to inhibit heat-induced vasodilatation in man. As a medium-strength corticosteroid, this medication is used to treat a variety of skin conditions (such as eczema, dermatitis, allergies, rash). Betamethasone reduces the swelling, itching, and redness that can occur in these types of conditions.

Definition

ChEBI: Betamethasone valerate is a steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester. It has a role as an anti-inflammatory drug. It is a steroid ester, a 20-oxo steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a primary alpha-hydroxy ketone. It is functionally related to a betamethasone.

Indications

Betamethasone valerate (Psorion, Beta-Val, Luxiq) is a synthetic fluorinated corticosteroid.

Manufacturing Process

The valerate is made from betamethasone as a starting material as follows: A suspension of 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene- 3,20-dione(betamethasone) (2 grams) in sodium dried benzene (500 ml) was distilled vigorously for a few minutes, toluene-p-sulfonic acid monohydrate (30 mg) and methyl orthovalerate (5 ml) were added and distillation was continued for 10 minutes. The mixture was then boiled under reflux for 1.5 hours after which time unreacted betamethasone alcohol (400 mg) was removed by filtration. The benzene solution was treated with solid sodium .bicarbonate and a few drops of pyridine, filtered and evaporated to dryness at about 50°C. The residue, in ether, was filtered through grade III basic alumina (20grams) to remove traces of unreacted betamethasone alcohol, the ether removed in vacuo and the residue of crude betamethasone 17,21- methyl orthovalerate was treated with acetic acid (20ml) and a few drops of water and left overnight at room temperature.
The acetic acid solution was poured into water (100 ml) and extracted with chloroform. The chloroform extracts were washed in turn with water, saturated sodium bicarbonate solution and water, dried and evaporated in vacuo. The residual gum was triturated with ether and a white crystalline solid (1.16 grams) isolated by filtration. Recrystallization from ether (containing a small amount of acetone)-petroleum ether gave 9α-fluoro-11β,21-dihydroxy-16β- methyl-17α-valeryloxypregna-1,4-diene-3,20-dione (871 mg) as fine needles.

brand name

Betatrex (Savage); Luxiq (Connetics); Valisone (Schering).

Therapeutic Function

Corticosteroid

Biochem/physiol Actions

Betamethasone 17-valerate is a synthetic glucocorticoid. It exhibitstherapeutic effects against various allergic and inflammatory skin diseases. Betamethasone 17-valerate also possesses anti-inflammatory properties.

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