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Ipratropium bromide

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Ipratropium bromide Basic information

Product Name:
Ipratropium bromide
Synonyms:
  • 8-Azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, (endo,syn)-, bromide
  • 8-Isopropylatropinium bromide
  • 3-alpha-Hydroxy-8-isopropyl-1-alpha-H,5-alpha-H-tropanium bromide (±)-tropate
  • 2-Methyl-2-[(piperidinomethyl)thio]propionic acid
  • 8-Azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide, (endo,syn)-
  • 8-Azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide, (endo,syn)-(+-)-
  • 8-Isopropylatropinium bromide (6CI, 7CI)
  • Atrovent forte
CAS:
22254-24-6
MF:
C20H30BrNO3
MW:
412.37
EINECS:
244-873-8
Product Categories:
  • Inhibitors
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Acetylcholine receptor
Mol File:
22254-24-6.mol
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Ipratropium bromide Chemical Properties

Melting point:
230-232°C
RTECS 
YM3700000
storage temp. 
Inert atmosphere,Room Temperature
solubility 
H2O: 10 mg/mL
form 
powder
color 
white
Water Solubility 
Freely soluble
Stability:
Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference
22254-24-6(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/22-36
Safety Statements 
26
WGK Germany 
3
Toxicity
LD50 in male, female mice (mg/kg): 1001, 1083 orally; 12.29, 14.97 i.v.; 300, 340 s.c.; LD50 in male, female rats (mg/kg): 1663, 1779 orally; 15.89, 15.70 i.v. (Sarafana)

MSDS

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Ipratropium bromide Usage And Synthesis

Pharmacology and toxicology

Ipratropium bromide is also known as isoprenaline, isopropyl atropine, isopropyl scopolamine, isopropyl atropine, ipratropium bromide, isopropyl atropine, isopropyl atropine bromide, ipratropium bromide, bromo ipratropium bromide. It is a white crystalline powder with bitter taste and melting point of 232℃-233℃. It is soluble in water, slightly soluble in ethanol and insoluble in other organic solvents. Chemical name is Brominated alpha (methylol) - phenylacetic acid -8- methyl -8- isopropyl- azacyclo [3, 2, 1]-3- octyl. It is an anticholinergic drug and can relax the bronchial smooth muscle.It has an antiasthmatic effect on chronic obstructive pulmonary disease.The effect is obvious, fast and enduring. Isopatropium also has the effect of controlling the secretion of the mucous glands and improving the ciliated movement, thereby reducing the obstruction of sputum to improve ventilation. At the same time, the decrease of sputum also relieves bronchospasm caused by bronchial irritation.It is used for the prevention and treatment of bronchial asthma and asthma type chronic bronchitis. Especially it is applicable to patients with a beta agonist that produces muscle tremor, tachycardia and can not tolerate such kind of drugs. The combination of this product and beta agonist can enhance the efficacy of each other.For example, it can be combined with fenoterol into aerosol (BERODU - AL) for treating asthma, chronic bronchitis and emphysema.Compared with beta adrenergic receptor stimulants (such as isopropylepinephrine), this product has less side effects on the cardiovascular system.
Compared with the beta 2- receptor stimulant (such as broncovaleas ), this product has a strong regulating effect on the amount of phlegm.

Indication

For the prevention and treatment of bronchial asthma and asthma type chronic bronchitis. Especially it is applicable to the patients with a beta agonist that produces muscle tremor, tachycardia and can not tolerate such drugs. The combination of this product and beta agonist can enhance the efficacy of each other. For example, it can be combined with fenoterol into aerosol (BERODU - AL) for treating asthma, chronic bronchitis and emphysema.

Precaution

  1. Prohibition It is prohibited for people who are allergic to soy lecithin or related foods such as soya and peanuts and those who are allergic to atropine or its derivatives or other ingredients of this product. It is also prohibited for the patients with hypertrophic obstructive cardiomyopathy, fast arrhythmia and pyloric obstruction.
  2. Cautious use It should be used in caution for patients with a tendency to narrow angle glaucoma, a benign prostatic hyperplasia, or a bladder neck obstruction.
  3. The use of beta adrenergic stimulants or xanthine agents can enhance the bronchiectasis of the drug.
  4. The most common non respiratory adverse reactions are headache, nausea, dry mouth, dysphonia, vertigo, anxiety, tachycardia, skeletal muscle fine tremor and palpitation.
  5. If the atomized ipratropium bromide is used alone or in combination with adrenaline beta 2- receptor agonist, when the atomizer enters the eye, it may have ocular complications, such as large pupil, increased intraocular pressure, angle closure glaucoma, and eye pain.
 

Drug overdose

Cholinesterase inhibitor can be used in the treatment of severe anticholinergic drug poisoning.

Adverse reaction

The adverse reaction of ipratropium bromide is similar to atropine, which can cause palpitation, headache, dizziness, nervousness, nausea and vomiting, alimentary tract pain, tremor, blurred vision, dry mouth and cough, dysuria, respiratory symptoms aggravating and rash.

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.

Uses

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

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.

Chemical Synthesis

Ipratropium bromide, 3α-hydroxy-8-isopropyl-1αH,5αH-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.

Ipratropium bromideSupplier

Wuhan lingjiu Biotechnology Co., Ltd Gold
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