Ipratropium bromide

Chemical properties

White Powder

Originator

Atrovent,Boehringer Ingelheim,W. Germany,1975

The Uses of Ipratropium bromide

Ipratropium Bromide is a nonselective muscarinic acetylcholine receptor antagonist; bronchodilator.

The Uses of Ipratropium bromide

N-Isopropyl quaternary salt of Atropine. Nonselective muscarinic acetylcholine receptor antagonist; bronchodilator

The Uses of Ipratropium bromide

This drug exhibits broncholytic action by reducing cholinergic influence on bronchial musculature (m-cholinoblocking action). It relieves bronchial spasms. It is used to treat and prevent minor and moderate bronchial asthma, especially asthma that is accompanied by cardiovascular system diseases.

What are the applications of Application

Ipratropium bromide is an N-isopropyl salt of atropine and muscarinic antagonist

Definition

ChEBI: The anhydrous form of the bromide salt of ipratropium. An anticholinergic drug, ipratropium bromide blocks the muscarinic cholinergic receptors in the smooth muscles of the bronchi in the lungs. This opens the bronchi, so providing relief in chronic obstru tive pulmonary disease and acute asthma.

Manufacturing Process

21 1.5 g (0.667 mol) of N-isopropyl-noratropine were dissolved at 60°C in 2.11 liters of absolute toluene in a 3-liter glass pressure tube. While the solution was still warm, 95 g (1 mol) of ice-cold methylbromide were added, and the pressure tube was sealed immediately thereafter. The reaction mixture was kept at 60°C for four days. After one hour of standing, the formation of crystals began. At the end of four days the crystals were separated by vacuum filtration at 60°C, washed with 600 cc of toluene at 60°C, and dried in vacuo in a drying cabinet at 100°C. Raw yield: 263.7 g (95.8% of theory). MP: 224°C to 225°C (decomp.). The raw product was refluxed with 2.5 liters of chloroform for 30 minutes, vacuum filtered whilehot, washed with 200 cc of chloroform, and dried in a vacuum drying cabinet at 100°C. Yield: 249 g (90.6% of theory). MP: 226°C to 228°C (decomp.). The purified product was recrystallized from 1.2 liters of n-propanol, washed with 200cc of n-propanol and dried in a vacuum drying cabinet at 100°C. Yield: 237 g (86.15% of theory). MP: 230°C to 232°C (decomp.). By evaporation of the mother liquor to 100 cc another 6.0 g of the pure product, MP 230°C to 231.5°C (decomp.), were obtained.

brand name

Atrovent (Boehringer Ingelheim).

Therapeutic Function

Bronchodilator

General Description

Ipratropium bromide, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane bromide (Atrovent), is a quaternaryammonium derivative of atropine. It is freely soluble inwater and ethanol but insoluble in chloroform and ether. Thesalt is stable in neutral and acidic solutions but rapidly hydrolyzedin alkaline solutions.

Biological Activity

Muscarinic antagonist, bronchodilator. N-Isopropyl salt of atropine.

Clinical Use

Ipratropium bromide is used in inhalation therapy toproduce dilation of bronchial smooth muscle for acute asthmaticattacks. The drug produces bronchodilation by competitiveinhibition of cholinergic receptors bound to smooth muscle of the bronchioles. Ipratropium may also act on thesurface of mast cells to inhibit ACh-enhanced release ofchemical mediators. The drug has a slow onset of action,within 5 to 15 minutes after being administered by inhalation,and should not be used alone for acute asthmatic attacks.The peak therapeutic effect from one dose is observedbetween 1 and 2 hours. The effects of the drug last for about6 hours. It has a half-life of 3.5 hours.

Clinical Use

Ipratropium bromide (Atrovent) is a quaternary amine derivative that is used via inhalation in the treatment of chronic obstructive pulmonary disease and to a lesser extent, asthma.

Synthesis

Ipratropium bromide, 3|á-hydroxy-8-isopropyl-1|áH,5|áH-tropanium bromide (23.3.6), is synthesized by reacting N-isopropylnoratropine with methyl bromide.

Veterinary Drugs and Treatments

Locally administered (inhaled) ipratropium bromide can be used for the adjunctive treatment of bronchospastic conditions.