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Details

Stereochemistry RACEMIC
Molecular Formula C20H30NO3.Br
Molecular Weight 412.361
Optical Activity ( + / - )
Defined Stereocenters 3 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IPRATROPIUM BROMIDE ANHYDROUS

SMILES

[Br-].CC(C)[N@+]1(C)[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3

InChI

InChIKey=LHLMOSXCXGLMMN-WDTICOSOSA-M
InChI=1S/C20H30NO3.BrH/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/q+1;/p-1/t16-,17+,18+,19?,21?;

HIDE SMILES / InChI

Molecular Formula C20H30NO3.Br
Molecular Weight 412.361
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 3 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C20H30NO3.Br
Molecular Weight 412.361
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 3 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

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".

Originator

Sources: Svenska lakartidningen (1962), 59, 3384-5.
Curator's Comment: Ravina, Enrique (2011). The evolution of drug discovery: from traditional medicines to modern drugs (1. Aufl. ed.). Weinheim: Wiley-VCH. p. 144.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ATROVENT HFA

Approved Use

ATROVENT 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 Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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%)
Nasal dryness (2%)
Epistaxis (2%)
Sources:
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)
Upper respiratory tract infection (1 patient)
Ear infection (1 patient)
Exacerbation of asthma (1 patient)
Sources:
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...
Other AEs:
Nasal disorder NOS (19 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 17.4 uM]
yes [IC50 2.5 uM]
yes [IC50 3.6 uM]
yes [IC50 30.5 uM]
yes [IC50 62.8 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Anticholinergic therapy for bronchiectasis.
2001
Bronchodilators for the prevention and treatment of chronic lung disease in preterm infants.
2001
Impact of patient characteristics on the risk of influenza/ILI-related complications.
2001
Management of acute exacerbations of chronic obstructive pulmonary disease.
2001 Aug
Evidence-based treatments for acute asthma.
2001 Dec
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
Childhood asthma.
2001 Nov
Towards evidence based medicine for paediatricians.
2001 Nov
Hospital-based management of acute asthmatic exacerbation: an assessment of physicians' behavior in Taiwan.
2001 Oct
The use of ipratropium bromide for the management of acute asthma exacerbation in adults and children: a systematic review.
2001 Oct
[RC-Cornet(R) improves the bronchodilating effect of Ipratropiumbromide (Atrovent(R)) inhalation in COPD-patients].
2001 Oct
Ipratropium bromide hydrofluoroalkane inhalation aerosol is safe and effective in patients with COPD.
2001 Oct
Graphical model checking with correlated response data.
2001 Oct 15
[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
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
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
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
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
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
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
Patents

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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:45:55 GMT 2023
Edited
by admin
on Fri Dec 15 18:45:55 GMT 2023
Record UNII
VJV4X1P2Z1
Record Status Validated (UNII)
Record Version
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Name Type Language
IPRATROPIUM BROMIDE ANHYDROUS
Common Name English
IPRATROPIUM BROMIDE [MI]
Common Name English
ipratropium bromide [INN]
Common Name English
Ipratropium bromide [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC R01AX03
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
WHO-ATC R03BB01
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C170538
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
CAS
22254-24-6
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID60858923
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
INN
3263
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
EVMPD
SUB40135
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
CHEBI
46659
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
DRUG BANK
DB00332
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
FDA UNII
VJV4X1P2Z1
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
RXCUI
1445143
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY RxNorm
EVMPD
SUB08276MIG
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
MERCK INDEX
m6387
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
244-873-8
Created by admin on Fri Dec 15 18:45:55 GMT 2023 , Edited by admin on Fri Dec 15 18:45:55 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY