ISOXSUPRINE HYDROCHLORIDE Chemical Properties

Melting point:

203-204°

storage temp. 

Inert atmosphere,2-8°C

solubility 

Sparingly soluble in water and in ethanol (96 per cent), practically insoluble in methylene chloride.

form 

Solid

pka

pKa 8.0 (Uncertain);9.8 (Uncertain)

color 

White to off-white

CAS DataBase Reference

579-56-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-50/53-63-50

Safety Statements 

36-61-60

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

RTECS 

DO8225000

HS Code 

2922504500

Hazardous Substances Data

579-56-6(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): 1750 orally; 164 i.p. (Goldenthal)

MSDS

• Language:English Provider:SigmaAldrich

ISOXSUPRINE HYDROCHLORIDE Usage And Synthesis

Description

Isoxsuprine is an adrenergic receptor modulator that has α-adrenergic receptor (α-AR) antagonist and β-AR agonist properties. It induces vasodilation of isolated equine common digital artery strips precontracted with norepinephrine, indicating an α-AR effect, and induces relaxation of isolated fowl cecum, an effect that can be blocked by the β-AR antagonist propranolol (Item Nos. 23349 | 17291). Isoxsuprine has antinociceptive effects in an acetic acid writhing test in mice. It also inhibits oxytocin-induced contractions in isolated rat uterus (IC₅₀ = 9.15 μM). It delays labor onset in rats by 31.63 hours when administered at a dose of 10 mg/kg per day on days 13 to 21 of gestation but increases heart rate with increasing concentration.

Chemical Properties

White Solid

Originator

Duvadilan,Duphar,France,1958

Uses

vasodilator

Uses

It is prescribed for the symptomatic relief of cerebrovascular insufficiency and improvement of circulation

Uses

As a vasilodator drug, Isoxsuprine Hydrochloride is used in veterinary medicine for the treatment of navicular syndrome and laminitis in horses. Isoxsuprine Hydrochloride has been shown to be a β-adrenoreceptor antagonist with β-adrenoreceptor agonistic properties, with both characteristics contributing to vasodilation and uterine relaxation. Studies suggest that Isoxsuprine Hydrochloride may be useful as a as a tocolytic agent in the treatment of preterm labour.

Uses

antiepileptic

Definition

ChEBI: Isoxsuprine hydrochloride is an alkylbenzene.

Manufacturing Process

To a solution of 30.7 g (0.203 mol) of 1-phenoxy-2-aminopropane in 150 ml of ethanol there was added 31.9 g (0.100 mol) of 1-(4'-benzyloxyphenyl)-2- bromopropanone-1. The mixture was heated to boiling temperature and the solution was then refluxed in a reflux condenser for 3 hours. Most of the ethanol was then distilled off in vacuo, Then to the residue there was addedabout 150 ml of diethyl ether. The hydrogen bromide salt of 1-phenoxy-2- aminopropane was filtered off and washed with diethyl ether.
The collected ethereal filtrates were acidified with 50 ml of 4 N hydrochloric acid and this solution was stirred vigorously. The hydrochloride of 1-(4'- benzyloxyphenyl)-2-(1'-methyl-2-phenoxy-ethylamino)propanone-1 precipitated out, was filtered off, washed with water and then with diethyl ether. Then this substance was dried in vacuo. The yield was 37.7 g, i.e., 89% of the theoretically possible yield, calculated on 1-(4'-benzyloxyphenyl)-2- bromine propanone-1. This substance had a light yellow color and melted at 197 to 198°C, while decomposing.
Then 21.89 g of the hydrochloride salt was dissolved in 600 ml of 80% aqueous ethanol. With the addition of a palladium carbon catalyst, this solution was hydrogenated at room temperature under a hydrogen pressure of about 1.1 atmospheres. After 2 mols hydrogen had been absorbed, the catalyst was filtered off and the filtrate was evaporated in vacuo until crystallization occurred. Then the crystals were dissolved by heating in the smallest possible quantity of water and after cooling, the crystallized substance was filtered off, washed with water and dried in vacuo. The yield was 6.80 g, i.e., 39% of the theoretically possible yield. The resultant product recrystallized from water melted at 203° to 204°C.

brand name

Vasodilan (Apothecon).

Therapeutic Function

Vasodilator

Veterinary Drugs and Treatments

Isoxsuprine is used in veterinary medicine principally for the treatment of navicular disease in horses; however, recent studies have shown disappointing efficacy when used orally. It has been used in humans for the treatment of cerebral vascular insufficiency, dysmenorrhea, and premature labor, but efficacies are unproven for these indications.
There has been an anecdotal report of isoxsuprine being helpful for treating dogs with a Raynaud’s-like syndrome (periodic digital cyanosis, onychogryphosis) (Carlotti 2002).

in vivo

animal stroke model, 1 mg/kg isoxsuprine was administered after a 90-minute occlusion of the right middle cerebral artery by iv injection at reperfusion. total infarct volume in isoxsuprine-treated group was 137±18 mm3 compared to 279±25 mm3 in control group [2].

References

1. r. s. ekert and c. g. macallister. isoxsuprine hydrochloride in the horse: a review. j. vet. pharmacol. ther. 2002, 25(2), 81-87 2. hill jw, thompson jf, carter mb. identification of isoxsuprine hydrochloride as a neuroprotectant in ischemic stroke through cell-based high-throughput screening. plos one. 2014 may 7; 9(5):e96761

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