Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H30NO3.Br.H2O |
Molecular Weight | 430.376 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 4 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Br-].CC(C)[N@+]1(C)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@@H](CO)C3=CC=CC=C3
InChI
InChIKey=KEWHKYJURDBRMN-KMYPTGJZSA-M
InChI=1S/C20H30NO3.BrH.H2O/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15;;/h4-8,14,16-19,22H,9-13H2,1-3H3;1H;1H2/q+1;;/p-1/t16-,17+,18+,19-,21?;;/m0../s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009241
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009241
Ipratropium (ipratropium bromide, ATROVENT® HFA) is a muscarinic antagonist structurally related to atropine but often considered safer and more effective for inhalation use. It is indicated for the maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. Ipratropium (ipratropium bromide, ATROVENT® HFA) is an anticholinergic (parasympatholytic) agent which, based on animal studies, appears to inhibit vagally-mediated reflexes by antagonizing the action of acetylcholine, the transmitter agent released at the neuromuscular junctions in the lung. Anticholinergics prevent the increases in intracellular concentration of Ca2+ which is caused by interaction of acetylcholine with the muscarinic receptors on bronchial smooth muscle.
CNS Activity
Sources: https://books.google.ru/books?id=ZyGsBAAAQBAJ&dq
Curator's Comment: Raeburn, David, Giembycz, Mark A. (2012). Rhinitis: Immunopathology and Pharmacotherapy. Springer. p. 133:
"Topical intranasal ipratropium bromide has limited central nervous system penetration".
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 |
0.49 nM [Ki] | ||
Target ID: CHEMBL211 |
1.5 nM [Ki] | ||
Target ID: CHEMBL245 |
0.51 nM [Ki] | ||
Target ID: CHEMBL1821 |
0.66 nM [Ki] | ||
Target ID: CHEMBL2035 |
1.7 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ATROVENT HFA Approved UseATROVENT HFA Inhalation Aerosol is indicated as a bronchodilator for maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. Launch Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.5 pg/mL |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
31.7 pg/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
35.4 pg/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.04 pg × h/mL |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
123 pg × h/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
131 pg × h/mL |
20 μg 4 times / day steady-state, respiratory dose: 20 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95.5% |
20 μg 4 times / day multiple, respiratory dose: 20 μg route of administration: Respiratory experiment type: MULTIPLE co-administered: ALBUTEROL |
IPRATROPIUM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Disc. AE: Nasal disorder NOS, Nasal dryness... AEs leading to discontinuation/dose reduction: Nasal disorder NOS (17%) Sources: Nasal dryness (2%) Epistaxis (2%) |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 43 Health Status: unhealthy Condition: common colds Age Group: 2 - 5 years Sex: M+F Population Size: 43 Sources: |
Disc. AE: Epistaxis... AEs leading to discontinuation/dose reduction: Epistaxis (1 patient) Sources: |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Disc. AE: Epistaxis, Upper respiratory tract infection... AEs leading to discontinuation/dose reduction: Epistaxis (1 patient) Sources: Upper respiratory tract infection (1 patient) Ear infection (1 patient) Exacerbation of asthma (1 patient) |
200 ug single, respiratory Highest studied dose Dose: 200 ug Route: respiratory Route: single Dose: 200 ug Sources: |
unhealthy, mean 40.7 years n = 20 Health Status: unhealthy Condition: stable chronic asthma Age Group: mean 40.7 years Sex: M+F Population Size: 20 Sources: |
Disc. AE: Nausea and vomiting... AEs leading to discontinuation/dose reduction: Nausea and vomiting (1 patient) Sources: |
42 ug 1 times / day steady, respiratory Recommended Dose: 42 ug, 1 times / day Route: respiratory Route: steady Dose: 42 ug, 1 times / day Sources: |
unhealthy, mean 42.6 years n = 99 Health Status: unhealthy Condition: rhinorrhea Age Group: mean 42.6 years Sex: M+F Population Size: 99 Sources: |
Other AEs: Nasal disorder NOS... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nasal disorder NOS | 17% Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Epistaxis | 2% Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Nasal dryness | 2% Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 18 - 75 years n = 96 Health Status: unhealthy Condition: perennial allergic rhinitis Age Group: 18 - 75 years Sex: M+F Population Size: 96 Sources: |
Epistaxis | 1 patient Disc. AE |
168 ug 3 times / day steady, respiratory Highest studied dose Dose: 168 ug, 3 times / day Route: respiratory Route: steady Dose: 168 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 43 Health Status: unhealthy Condition: common colds Age Group: 2 - 5 years Sex: M+F Population Size: 43 Sources: |
Ear infection | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Epistaxis | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Exacerbation of asthma | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Upper respiratory tract infection | 1 patient Disc. AE |
84 ug 3 times / day steady, respiratory Highest studied dose Dose: 84 ug, 3 times / day Route: respiratory Route: steady Dose: 84 ug, 3 times / day Sources: |
unhealthy, 2 - 5 years n = 187 Health Status: unhealthy Condition: allergies Age Group: 2 - 5 years Sex: M+F Population Size: 187 Sources: |
Nausea and vomiting | 1 patient Disc. AE |
200 ug single, respiratory Highest studied dose Dose: 200 ug Route: respiratory Route: single Dose: 200 ug Sources: |
unhealthy, mean 40.7 years n = 20 Health Status: unhealthy Condition: stable chronic asthma Age Group: mean 40.7 years Sex: M+F Population Size: 20 Sources: |
Nasal disorder NOS | 19 patients | 42 ug 1 times / day steady, respiratory Recommended Dose: 42 ug, 1 times / day Route: respiratory Route: steady Dose: 42 ug, 1 times / day Sources: |
unhealthy, mean 42.6 years n = 99 Health Status: unhealthy Condition: rhinorrhea Age Group: mean 42.6 years Sex: M+F Population Size: 99 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 17.4 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 2.5 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 3.6 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 30.5 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 6,21 |
yes [IC50 62.8 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/27676604/ Page: 7,21 |
strong | |||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Asthma medications and their potential adverse effects in the elderly: recommendations for prescribing. | 2001 |
|
Standard dose of inhaled albuterol significantly increases QT dispersion compared to low dose of albuterol plus ipratropium bromide therapy in moderate to severe acute asthma attacks in children. | 2001 Dec |
|
Randomized trial of the addition of ipratropium bromide to albuterol and corticosteroid therapy in children hospitalized because of an acute asthma exacerbation. | 2001 Dec |
|
Effect of ipratropium bromide on airway and pulmonary muscarinic receptors in a rat model of chronic obstructive pulmonary disease. | 2001 Jan |
|
Pharmacokinetics and tissue distribution of the anticholinergics tiotropium and ipratropium in the rat and dog. | 2001 Jul |
|
Does adding ipratropium to salbutamol (albuterol) help children with asthma? | 2001 Nov |
|
Lower arrythmogenic risk of low dose albuterol plus ipratropium. | 2001 Oct |
|
Drug therapy of childhood asthma. | 2001 Sep |
|
[Effect of anticholinergic therapy on myocardial reserve dynamics in patients with chronic obstructive bronchitis]. | 2001 Sep-Dec |
|
Cold-induced rhinitis in skiers--clinical aspects and treatment with ipratropium bromide nasal spray: a randomized controlled trial. | 2001 Sep-Oct |
|
[Asthma follow-up after treatment of status asthmaticus in ICU Pneumonology Department in Warsaw Medical University]. | 2002 |
|
Prevention and treatment of respiratory syncytial virus bronchiolitis and postbronchiolitic wheezing. | 2002 |
|
Role of cholinergic reflexes on the bronchoconstrictor reactivity to neurokinin a in allergic dogs. | 2002 |
|
Heliox for treatment of exacerbations of chronic obstructive pulmonary disease. | 2002 |
|
Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine. | 2002 |
|
Tiotropium bromide. | 2002 |
|
[Pharmacodynamics of inhalation broncholytic agents introduced in a single dose by nebulizer in patients with severe exacerbation of bronchial asthma]. | 2002 |
|
Management of children with severe asthma exacerbation in the emergency department. | 2002 |
|
Pressurised metered-dose inhalers versus all other hand-held inhalers devices to deliver bronchodilators for chronic obstructive pulmonary disease. | 2002 |
|
Anticholinergic drugs for wheeze in children under the age of two years. | 2002 |
|
Pharmacogenetics, pharmacogenomics and airway disease. | 2002 |
|
Pharmacodynamic steady state of tiotropium in patients with chronic obstructive pulmonary disease. | 2002 Apr |
|
Do bronchodilators have an effect on bronchiolitis? | 2002 Apr |
|
Differential response of wheezes and ruttles to anticholinergics. | 2002 Apr |
|
Intravenous versus oral corticosteroids for treatment of acute asthma exacerbations. | 2002 Apr |
|
Airways reactivity in patients with CF. | 2002 Aug |
|
Hospitalizations and mortality in the Lung Health Study. | 2002 Aug 1 |
|
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139]. | 2002 Aug 5 |
|
Clinical review: severe asthma. | 2002 Feb |
|
[Benefits of ipratropium bromide in the management of asthmatic crises in the emergency department]. | 2002 Feb |
|
Randomized, double-blind, placebo-controlled trial of intravenous salbutamol and nebulized ipratropium bromide in early management of severe acute asthma in children presenting to an emergency department. | 2002 Feb |
|
Improved health outcomes in patients with COPD during 1 yr's treatment with tiotropium. | 2002 Feb |
|
Other option in bronchiolitis. | 2002 Feb |
|
Heterogeneity of release-inhibiting muscarinic autoreceptors in heart atria and urinary bladder: a study with M(2)- and M(4)-receptor-deficient mice. | 2002 Feb |
|
Dry powder ipratropium bromide is as safe and effective as metered-dose inhaler formulation: a cumulative dose-response study in chronic obstructive pulmonary disease patients. | 2002 Feb |
|
Treatment of patients hospitalized for exacerbations of chronic obstructive pulmonary disease: comparison of an oral/metered-dose inhaler regimen and an intravenous/nebulizer regimen. | 2002 Feb |
|
Effects of inhaled ipratropium bromide on breathing mechanics and gas exchange in exercising horses with chronic obstructive pulmonary disease. | 2002 Jan |
|
The incremental shuttle walking test in elderly people with chronic airflow limitation. | 2002 Jan |
|
Emergency department asthma: compliance with an evidence-based management algorithm. | 2002 Jul |
|
Management of acute, severe asthma in children. | 2002 Jul-Aug |
|
Hospital management of children with acute asthma exacerbations in Kuwait: adherence to international guidelines. | 2002 Jul-Sep |
|
Treatment and quality of life in patients with chronic obstructive pulmonary disease. | 2002 Jun |
|
The role of anticholinergics in acute asthma treatment: an evidence-based evaluation. | 2002 Jun |
|
Understanding and use of inhaler medication by asthmatics in specialty care in Trinidad: a study following development of Caribbean guidelines for asthma management and prevention. | 2002 Jun |
|
Mydriasis due to self-administered inhaled ipratropium bromide. | 2002 Mar |
|
In children hospitalized for asthma exacerbations, does adding ipratropium bromide to albuterol and corticosteroids improve outcome? | 2002 Mar |
|
Use of a mucus clearance device enhances the bronchodilator response in patients with stable COPD. | 2002 Mar |
|
Comparison of nebulized budesonide and oral prednisolone with placebo in the treatment of acute exacerbations of chronic obstructive pulmonary disease: a randomized controlled trial. | 2002 Mar 1 |
|
[Effect of ipratropium bromide on calcium activated potassium channel in tracheal smooth muscle cells from chronically hypoxic rats]. | 2002 May |
|
What is the optimal treatment strategy for chronic obstructive pulmonary disease exacerbations? | 2002 May |
Sample Use Guides
The usual starting dose of ATROVENT® HFA is two inhalations four times a day. Patients may take additional inhalations as required; however, the total number of inhalations should not exceed 12 in 24 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7952627
Ba 679 BR, atropine, and ipratropium bromide inhibited electrical field stimulation (EFS)-induced contraction with IC50 values of 0.17, 0.74, and 0.58 nM, respectively, in guinea pig trachea. Ba 679 BR had a slower onset and longer duration of action than atropine or ipratropium bromide (the times required to attain 50% of the maximum response were 34.8, 3.8, and 7.6 min, respectively, and the times required for 50% recovery of the response were 540, 31.6, and 81.2 min, respectively).
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QR01AX03
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WHO-ATC |
R03AL01
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WHO-ATC |
R03AL02
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NCI_THESAURUS |
C319
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NCI_THESAURUS |
C29704
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WHO-VATC |
QR03AL01
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WHO-VATC |
QR03BB01
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WHO-ATC |
R03BB01
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WHO-ATC |
R01AX03
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WHO-ESSENTIAL MEDICINES LIST |
25.1
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WHO-VATC |
QR03AL02
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SUB22932
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J697UZ2A9J
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C29128
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DBSALT000208
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1347507
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203212
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DTXSID3045772
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66985-17-9
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46659
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100000091674
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759613
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CHEMBL1621597
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J697UZ2A9J
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5957
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IPRATROPIUM BROMIDE
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1309404
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ACTIVE MOIETY
SUBSTANCE RECORD