Oxitropium bromide

Last updated
Oxitropium bromide
Oxitropium bromide.svg
Clinical data
Trade names Oxivent, Tersigan, Tersigat, Ventilat
Other namesN-Ethylscopolammonium bromide; Ba 253; Ba 253BR-L; Ba 253Br; Hyoscine ethobromide; N-Ethylnorscopolamine methyl bromide; Scopolamine ethobromide
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • (8r)-6β,7β-Epoxy-8-ethyl-3α-hydroxy-1αH,5αH-tropanium bromide (−)-tropate
CAS Number
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.045.543 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H26BrNO4
Molar mass 412.324 g·mol−1
3D model (JSmol)
  • [Br-].OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@@H]3[C@H]4O[C@H]4[C@H](C2)[N+]3(C)CC
  • InChI=1S/C19H26NO4.BrH/c1-3-20(2)15-9-13(10-16(20)18-17(15)24-18)23-19(22)14(11-21)12-7-5-4-6-8-12;/h4-8,13-18,21H,3,9-11H2,1-2H3;1H/q+1;/p-1/t13-,14-,15-,16+,17-,18+,20?;/m1./s1
  • Key:LCELQERNWLBPSY-KHSTUMNDSA-M

Oxitropium bromide (trade names Oxivent, Tersigan) is an anticholinergic used as a bronchodilator for the treatment of asthma and chronic obstructive pulmonary disease. [1]

It was patented in 1966 and approved for medical use in 1983. [2]

Synthesis

Oxitropium synthesis.svg

The natural product, norscopolamine (1), [3] is converted by two alkylation reactions into oxitropium bromide. The first, with bromoethane, gives the N-ethyl intermediate (2), which is treated with bromomethane. [4] [5] [6]

Related Research Articles

A bronchodilator or broncholytic is a substance that dilates the bronchi and bronchioles, decreasing resistance in the respiratory airway and increasing airflow to the lungs. Bronchodilators may be originating naturally within the body, or they may be medications administered for the treatment of breathing difficulties, usually in the form of inhalers. They are most useful in obstructive lung diseases, of which asthma and chronic obstructive pulmonary disease are the most common conditions. Although this remains somewhat controversial, they might be useful in bronchiolitis and bronchiectasis. They are often prescribed but of unproven significance in restrictive lung diseases.

<span class="mw-page-title-main">Pergolide</span> Dopamine agonist medication

Pergolide, sold under the brand name Permax and Prascend (veterinary) among others, is an ergoline-based dopamine receptor agonist used in some countries for the treatment of Parkinson's disease. Parkinson's disease is associated with reduced dopamine activity in the substantia nigra of the brain. Pergolide acts on many of the same receptors as dopamine to increase receptor activity.

<span class="mw-page-title-main">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the trade name Atrovent among others, is a type of anticholinergic medication which is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

Beta<sub>2</sub>-adrenergic agonist Compounds that bind to and activate adrenergic beta-2 receptors

Beta2-adrenergic agonists, also known as adrenergic β2 receptor agonists, are a class of drugs that act on the β2 adrenergic receptor. Like other β adrenergic agonists, they cause smooth muscle relaxation. β2 adrenergic agonists' effects on smooth muscle cause dilation of bronchial passages, vasodilation in muscle and liver, relaxation of uterine muscle, and release of insulin. They are primarily used to treat asthma and other pulmonary disorders. Bronchodilators are considered an important treatment regime for chronic obstructive pulmonary disease (COPD) and are usually used in combination with short acting medications and long acting medications in a combined inhaler.

<span class="mw-page-title-main">Phendimetrazine</span> Pharmaceutical drug

Phendimetrazine is a stimulant drug of the morpholine chemical class used as an appetite suppressant.

Ipratropium bromide/salbutamol, sold under the brand name Combivent among others, is a combination medication used to treat chronic obstructive pulmonary disease (COPD). It contains ipratropium and salbutamol.

<span class="mw-page-title-main">Phenmetrazine</span> Chemical compound

Phenmetrazine is a stimulant drug first synthesized in 1952 and originally used as an appetite suppressant, but withdrawn from the market in the 1980s due to widespread abuse. It was initially replaced by its analogue phendimetrazine which functions as a prodrug to phenmetrazine, but now it is rarely prescribed, due to concerns of abuse and addiction. Chemically, phenmetrazine is a substituted amphetamine containing a morpholine ring.

<span class="mw-page-title-main">Long-acting beta-adrenoceptor agonist</span> Drug prescribed for asthma patients

Long-acting β adrenoceptor agonists (LABAs) are beta-adrenergic agonists usually prescribed for moderate-to-severe persistent asthma and chronic obstructive pulmonary disease (COPD).

C.H. Boehringer Sohn AG & Co. KG is the parent company of the Boehringer Ingelheim group, which was founded in 1885 by Albert Boehringer (1861–1939) in Ingelheim am Rhein, Germany. As of 2018, Boehringer Ingelheim is one of the world's largest pharmaceutical companies, and the largest private one. Headquartered in Ingelheim, it operates globally with 146 affiliates and more than 47,700 employees. Unlike most large pharmaceutical companies which are listed, the company is private and fully owned by the Boehringer, Liebrecht and von Baumbach families. The company's key areas of interest are: respiratory diseases, metabolism, immunology, oncology and diseases of the central nervous system. Boehringer Ingelheim is a full member of the European Federation of Pharmaceutical Industries and Associations (EFPIA). The corporate logo of Boehringer Ingelheim depicts a stylized rendition of the central section of the imperial palace of Charlemagne.

<span class="mw-page-title-main">Repaglinide</span> Chemical compound

Repaglinide is an antidiabetic drug in the class of medications known as meglitinides, and was invented in 1983. Repaglinide is a medication used in addition to diet and exercise for blood sugar control in type 2 diabetes. The mechanism of action of repaglinide involves promoting insulin release from β-islet cells of the pancreas; like other antidiabetic drugs, a main side effect concern is hypoglycemia. It is sold by Novo Nordisk under the name of Prandin in the United States, Gluconorm in Canada, Surepost in Japan, Repaglinide in Egypt, and Novonorm elsewhere. In Japan it is produced by Dainippon Sumitomo Pharma.

<span class="mw-page-title-main">Gliquidone</span> Chemical compound

Gliquidone is an anti-diabetic medication in the sulfonylurea class. It is classified as a second-generation sulfonylurea. It is used in the treatment of diabetes mellitus type 2. It is marketed by the pharmaceutical company Boehringer Ingelheim (Germany).

<span class="mw-page-title-main">Methylnaltrexone</span> Medication in the treatment for Opioid-Induced Constipation

Methylnaltrexone, used in form of methylnaltrexone bromide, is a medication that acts as a peripherally acting μ-opioid receptor antagonist that acts to reverse some of the side effects of opioid drugs such as constipation without significantly affecting pain relief or precipitating withdrawals. Because MNTX is a quaternary ammonium cation, it cannot cross the blood–brain barrier, and so has antagonist effects throughout the body, counteracting effects such as itching and constipation, but without affecting opioid effects in the brain such as pain relief. However, since a significant fraction of opioid analgesia can be mediated by opioid receptors on peripheral sensory neurons, particularly in inflammatory conditions such as arthritis, traumatic or surgical pain, MNTX may increase pain under such circumstances.

<span class="mw-page-title-main">Triflubazam</span> Chemical compound

Triflubazam is a drug which is a 1,5-benzodiazepine derivative, related to clobazam. It has sedative and anxiolytic effects, with a long half-life and duration of action.

<span class="mw-page-title-main">Talipexole</span> Chemical compound

Talipexole is a dopamine agonist that is marketed as a treatment for Parkinson's Disease in Japan by Boehringer Ingelheim; it was introduced in 1996. As of December 2014 it was not approved for marketing in the US nor in Europe.

<span class="mw-page-title-main">Pimobendan</span> Chemical compound

Pimobendan, sold under the brand name Vetmedin among others, is a veterinary medication. It is a calcium sensitizer and a selective inhibitor of phosphodiesterase 3 (PDE3) with positive inotropic and vasodilator effects.

<span class="mw-page-title-main">Tiotropium bromide</span> Long-acting bronchodilator in the maintenance of COPD and asthma

Tiotropium bromide, sold under the brand name Spiriva among others, is a long-acting bronchodilator used in the management of chronic obstructive pulmonary disease (COPD) and asthma. Specifically it is used during periods of breathing difficulty to prevent them from getting worse, rather than to prevent them from happening. It is used by inhalation through the mouth. Onset typically begins within half an hour and lasts for 24 hours.

<span class="mw-page-title-main">Olodaterol</span> Chemical compound

Olodaterol is an ultra-long-acting β adrenoreceptor agonist (ultra-LABA) used as an inhalation for treating people with chronic obstructive pulmonary disease (COPD). It is manufactured by Boehringer Ingelheim.

<span class="mw-page-title-main">Bunitrolol</span> Chemical compound

Bunitrolol is a beta-adrenergic antagonist.

<span class="mw-page-title-main">Indacaterol/glycopyrronium bromide</span> Combination drug

Indacaterol/glycopyrronium bromide, sold under the brand name Ultibro Breezhaler among others, is a fixed-dose combination medication for inhalation consisting of the following two active ingredients:

Fluticasone furoate/umeclidinium bromide/vilanterol, sold under the brand name Trelegy Ellipta among others, is a fixed-dose combination inhaled medication that is used for the maintenance treatment of chronic obstructive pulmonary disease (COPD). The medications work in different ways: fluticasone furoate is an inhaled corticosteroid (ICS), umeclidinium is a long-acting muscarinic antagonist (LAMA), and vilanterol is a long-acting beta-agonist (LABA).

References

  1. Restrepo RD (July 2007). "Use of inhaled anticholinergic agents in obstructive airway disease". Respiratory Care. 52 (7): 833–51. PMID   17594728.
  2. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 447. ISBN   9783527607495.
  3. Ripperger, H (1995). "(S)-scopolamine and (S)-norscopolamine from Atropanthe sinensis". Planta Med. 61: 292–3. doi:10.1055/s-2006-958082. PMID   7617778.
  4. Rolf Banholzer, Werner Schulz, Gerhard Walther, Helmut Wick, Karl Zeile, U.S. patent 3,472,861 (1969 to Boehringer Sohn Ingelheim).
  5. Rolf Banholzer, Werner Schulz, & Karl Zeile, U.S. patent 3,538,102 (1970 to CH Boehringer Sohn AG and Co KG, Boehringer Ingelheim GmbH).
  6. "Oxitropium bromide". Thieme. Retrieved 2024-07-01.