Chemical Properties
White Powder
Originator
Atrovent,Boehringer Ingelheim,W. Germany,1975
Uses
N-Isopropyl quaternary salt of Atropine. Nonselective muscarinic acetylcholine receptor antagonist; bronchodilator
Uses
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.
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 (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.
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.
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.
