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Details

Stereochemistry RACEMIC
Molecular Formula C20H30NO3
Molecular Weight 332.4579
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of IPRATROPIUM

SMILES

CC(C)[N@@+]1(C)[C@@]2([H])CC[C@]1([H])C[C@@]([H])(C2)OC(=O)[C@@]([H])(CO)c3ccccc3

InChI

InChIKey=OEXHQOGQTVQTAT-VQCHGODESA-N
InChI=1S/C20H30NO3/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/q+1/t16-,17+,18+,19-,21?/m0/s1

HIDE SMILES / InChI

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

1.10142725E12
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
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options?
2001
Management of acute exacerbations of chronic obstructive pulmonary disease.
2001 Aug
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
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
Childhood asthma.
2001 Nov
Towards evidence based medicine for paediatricians.
2001 Nov
Lower arrythmogenic risk of low dose albuterol plus ipratropium.
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
Drug therapy of childhood asthma.
2001 Sep
Inhaled formoterol dry powder versus ipratropium bromide in chronic obstructive pulmonary disease.
2001 Sep 1
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
[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
[Benefits of ipratropium bromide in the management of asthmatic crises in the emergency department].
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
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
In children hospitalized for asthma exacerbations, does adding ipratropium bromide to albuterol and corticosteroids improve outcome?
2002 Mar
[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).
Name Type Language
IPRATROPIUM
VANDF   WHO-DD  
Common Name English
IPRATROPIUM ION
Common Name English
IPRATROPIUM [VANDF]
Common Name English
IPRATROPIUM [WHO-DD]
Common Name English
IPRATROPIUM CATION
Common Name English
8-AZONIABICYCLO(3.2.1)OCTANE, 3-(3-HYDROXY-1-OXO-2-PHENYLPROPOXY)-8-METHYL-8-(1-METHYLETHYL)-, (3-ENDO,8-SYN)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
NDF-RT N0000175574
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
WHO-ATC R01AX03
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
NDF-RT N0000175370
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
LIVERTOX 513
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
NCI_THESAURUS C319
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
WHO-ATC R03BB01
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
WHO-ATC R03AL02
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
WHO-ATC R03AL01
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
Code System Code Type Description
WIKIPEDIA
Ipratropium
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
MESH
D009241
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
RXCUI
7213
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
ALTERNATIVE
NCI_THESAURUS
C61794
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
DRUG CENTRAL
1475
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
CAS
60205-81-4
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
IUPHAR
325
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
EVMPD
SUB02767MIG
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
DRUG BANK
DB00332
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
EPA CompTox
60205-81-4
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
LACTMED
Ipratropium
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
RXCUI
1546373
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY
FDA UNII
GR88G0I6UL
Created by admin on Sat Jun 26 06:48:24 UTC 2021 , Edited by admin on Sat Jun 26 06:48:24 UTC 2021
PRIMARY