Ipratropium is a quaternary ammonium derivative of atropine^[4] that acts as an anticholinergic agent.^[1] It is commonly administered through inhalation which allows producing a local effect without presenting a significant systemic absorption.^[4]

Ipratropium as a therapeutic agent was developed by Boehringer Ingelheim and its first monotherapy product was FDA approved in 1986.^[11] On the other hand, the combination product of ipratropium and albuterol was approved in 1996.^[12]

Structure

Similar Structures

Synonyms

bromuro de ipratropio
Ipratropium cation
Ipratropium ion

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Ipratropium bromide anhydrous	VJV4X1P2Z1	22254-24-6	LHLMOSXCXGLMMN-WDTICOSOSA-M
Ipratropium bromide monohydrate	J697UZ2A9J	66985-17-9	KEWHKYJURDBRMN-XSAPEOHZSA-M
Ipratropium chloride	Not Available	Not Available	MQIPRYDNKGFOGV-WDTICOSOSA-M

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Atrovent	Spray, metered	21 ug/1	Nasal	Physicians Total Care, Inc.	2006-03-31	Not applicable
Atrovent	Solution	250 mcg	Respiratory (inhalation)	Boehringer Ingelheim (Canada) Ltd Ltee	1988-12-31	2007-10-11
Atrovent	Spray, metered	21 ug/1	Nasal	Boehringer Ingelheim Pharmaceuticals, Inc.	1996-01-01	2018-12-01
Atrovent	Spray, metered	42 ug/1	Nasal	Boehringer Ingelheim Pharmaceuticals, Inc.	1996-01-01	2018-12-01
Atrovent	Spray, metered	42 ug/1	Nasal	Remedy Repack	2018-03-14	2018-03-14
Atrovent	Aerosol, metered	17 ug/1	Respiratory (inhalation)	Physicians Total Care, Inc.	1995-08-07	2006-01-20
Atrovent	Aerosol, metered	18 ug/1	Respiratory (inhalation)	Boehringer Ingelheim	1986-12-19	2006-06-02
Atrovent	Spray, metered	42 ug/1	Nasal	Physicians Total Care, Inc.	2003-05-23	2011-06-30
Atrovent HFA	Aerosol, metered	20 mcg	Respiratory (inhalation)	Boehringer Ingelheim (Canada) Ltd Ltee	2004-03-24	Not applicable
Atrovent HFA	Aerosol, metered	17 ug/1	Respiratory (inhalation)	Rpk Pharmaceuticals, Inc.	2005-05-01	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-ipravent Solution - Inh 250mcg/ml	Solution	250 mcg	Respiratory (inhalation)	Apotex Corporation	1994-12-31	Not applicable
Apo-ipravent Sterules	Solution	125 mcg	Respiratory (inhalation)	Apotex Corporation	2001-08-28	Not applicable
Apo-ipravent Sterules	Solution	250 mcg	Respiratory (inhalation)	Apotex Corporation	1998-07-09	Not applicable
Dom-ipratropium	Solution	21 mcg	Nasal	Dominion Pharmacal	1999-09-15	Not applicable
Dom-ipratropium 125 Mcg/ml	Liquid	125 mcg	Respiratory (inhalation)	Dominion Pharmacal	Not applicable	Not applicable
Dom-ipratropium 250 Mcg/ml (1 Ml)	Liquid	250 mcg	Respiratory (inhalation)	Dominion Pharmacal	Not applicable	Not applicable
Dom-ipratropium 250 Mcg/ml (2 Ml)	Liquid	250 mcg	Respiratory (inhalation)	Dominion Pharmacal	Not applicable	Not applicable
Dom-ipratropium 250 Mcg/ml (20 Ml)	Liquid	250 mcg	Respiratory (inhalation)	Dominion Pharmacal	Not applicable	Not applicable
Ipratropium Bromide	Spray, metered	42 ug/1	Nasal	Apotex Corporation	2003-04-18	2011-05-19
Ipratropium bromide	Spray, metered	21 ug/1	Nasal	Bausch & Lomb Incorporated	2003-03-31	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Apo-salvent-ipravent Sterules	Ipratropium bromide monohydrate (0.5 mg) + Salbutamol (2.5 mg)	Solution	Respiratory (inhalation)	Apotex Corporation	2006-08-25	Not applicable
Combivent	Ipratropium bromide monohydrate (18 ug/1) + Salbutamol sulfate (90 ug/1)	Aerosol, metered	Respiratory (inhalation)	Physicians Total Care, Inc.	2000-09-18	2013-06-30
Combivent	Ipratropium bromide monohydrate (18 ug/1) + Salbutamol sulfate (90 ug/1)	Aerosol, metered	Respiratory (inhalation)	Boehringer Ingelheim	1997-06-01	2014-09-30
Combivent Inhalation Aerosol	Ipratropium bromide monohydrate (20 mcg) + Salbutamol sulfate (120 mcg)	Aerosol, metered	Oral; Respiratory (inhalation)	Boehringer Ingelheim (Canada) Ltd Ltee	1995-12-31	2007-10-02
Combivent Respimat	Ipratropium bromide monohydrate (20 ug/1) + Salbutamol sulfate (120 ug/1)	Spray, metered	Respiratory (inhalation)	Boehringer Ingelheim	2012-07-01	Not applicable
Combivent Respimat	Ipratropium bromide monohydrate (20 mcg) + Salbutamol (100 mcg)	Solution	Respiratory (inhalation)	Boehringer Ingelheim (Canada) Ltd Ltee	2014-09-16	Not applicable
Combivent Udv	Ipratropium bromide monohydrate (0.2 mg) + Salbutamol (1 mg)	Solution	Respiratory (inhalation)	Boehringer Ingelheim (Canada) Ltd Ltee	1997-07-25	Not applicable
DuoNeb	Ipratropium bromide monohydrate (0.5 mg/3mL) + Salbutamol sulfate (2.5 mg/3mL)	Solution	Respiratory (inhalation)	Physicians Total Care, Inc.	2007-06-06	2012-06-30
DuoNeb	Ipratropium bromide monohydrate (0.5 mg/3mL) + Salbutamol sulfate (2.5 mg/3mL)	Solution	Respiratory (inhalation)	Mylan Specialty	2011-02-15	2014-06-30
Duovent Udv	Ipratropium bromide monohydrate (0.125 mg) + Fenoterol hydrobromide (0.3125 mg)	Solution	Oral; Respiratory (inhalation)	Boehringer Ingelheim (Canada) Ltd Ltee	1995-12-31	2017-01-31

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Ipratropium Bromide	Ipratropium bromide monohydrate (0.5 mg/1mL)	Solution	Respiratory (inhalation)	Cantrell Drug Company	2012-10-12	2015-01-14

International/Other Brands

Aerovent (Teva) / Apovent (Apotex Inc.) / Atronase (Boehringer Ingelheim) / Ipraxa (Ivax) / Ipvent (Cipla Medpro) / Rhinovent (Boehringer Ingelheim) / Rinatec (Boehringer Ingelheim) / Rinovagos (Valeas)

Categories

UNII

GR88G0I6UL

CAS number

60205-81-4

Weight

Average: 332.463
Monoisotopic: 332.22202025

Chemical Formula

C₂₀H₃₀NO₃

InChI Key

OEXHQOGQTVQTAT-BHIXFJMTSA-N

InChI

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?

IUPAC Name

(1R,3R,5S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium

SMILES

[H][C@]12CC[C@]([H])(C[C@@H](C1)OC(=O)C(CO)C1=CC=CC=C1)[N+]2(C)C(C)C

Pharmacology

Indication

Inhaled ipratropium is indicated in combination with inhaled beta-agonist systemic corticosteroids for the management of severe exacerbations of asthma flares requiring treatment.^[1]

Asthma exacerbations are characterized by a progressive increase in one or more of asthma symptoms accompanied by a decrease in expiratory flow.^[13]

As a single agent, ipratropium was indicated for the symptomatic relief of rhinorrhea associated with the common cold or seasonal allergic rhinitis for patients 5 years or older. It does not alleviate nasal congestion nor sneezing.^[Label]

Rhinorrhea refers to recurrent or chronic watery nasal discharge. This condition is debilitating and its pathogenesis and etiology is complex and not very well understood presenting very substantial cost burden.^[14]

Additionally, ipratropium is indicated as a bronchodilator for maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease including chronic bronchitis and emphysema.^[Label]

The chronic obstructive pulmonary disease includes a large number of conditions characterized by breathlessness. As this includes several conditions, the etiology, symptoms, and treatments are diverse.^[15]

Ipratropium has also been studied to be used for the treatment of sialorrhea.^[2]

Sialorrhea is a common symptom that accompanies different neurologic conditions and it is characterized by drooling or excessive salivation.^[5]

Associated Conditions

Pharmacodynamics

Ipratropium is a short-acting agent that inhibits the parasympathetic nervous system at the level of the airway which then produces bronchodilatation. The effect of this agent starts after 1-2 hours and it is known to last only from 4 to 6 hours.^[3] As part of the effect, ipratropium relaxes the bronchial airways which reverse the narrowing that accounts for wheezy breathing, chest tightness, cough and abnormal gas exchange.^[6]

In clinical trials where ipratropium was used in the initial management of status asthmaticus, it was demonstrated a clear benefit in pulmonary function in children and adults. However, the continuous use of ipratropium after an acute asthmatic attack is not proven to be significantly advantageous^[1] nor the prophylactic administration of this agent.^[8]

Mechanism of action

Ipratropium acts as an antagonist of the muscarinic acetylcholine receptor.^[1] This effect produces the inhibition of the parasympathetic nervous system in the airways and hence, inhibit their function. The function of the parasympathetic system in the airway is to generate bronchial secretions and constriction and hence, the inhibition of this action can lead to bronchodilation and fewer secretions.^[3]

At the cellular level, the diameter of the airways is controlled by the release of acetylcholine into the muscle cells causing them to contract and producing a narrow airway. Thus administration of ipratropium stops the activity of acetylcholine in the smooth muscle preventing the contraction and producing relaxed airways.^[6]

Target	Actions	Organism
AMuscarinic acetylcholine receptor M1	antagonist	Humans
AMuscarinic acetylcholine receptor M2	antagonist	Humans
AMuscarinic acetylcholine receptor M3	antagonist	Humans

Absorption

Ipratropium is a topically active but poorly absorbed agent.^[7] The lack of absorption potential in the mucosal surfaces is associated with the presence of a charge in the 5-valent nitrogen. The molecule itself presents very large topic effectiveness however, it does not produce detectable blood levels nor systemic effects.^[8]

Serum levels of ipratropium after oral or inhaled administration are very low, corresponding to only 1-2% of the administered dose. These low levels peak after 1-2 hours and it presents a low bioavailability of 2%.^[8]

Volume of distribution

Ipratropium has a volume of distributions of 4.6 L/kg and hence, it is known to be highly distributed in the tissues.^[16]

Protein binding

The protein binding of ipratropium is very low as the level of circulating ipratropium is very minimal. The bound state represents only from 0-9% of the administered dose.^[10]

Metabolism

Ipratropium is metabolized in the gastrointestinal tract by the activity of the cytochrome P-450 isoenzymes.^[3] From the orally administered dose, about 90% of the dose is excreted unchanged. The absorbed portion is partially metabolized by ester hydrolysis to inactive metabolites, tropic acid and tropane.^[9]

Route of elimination

About 80-100% of the administered dose of ipratropium is excreted in the urine leaving less than 20% of the dose to be eliminated through the feces.^[3] From the urine eliminated portion, almost all the drug is found unchanged.^[8]

However, when ipratropium is orally administered, due to its low absorption, most of the dose is recovered in the feces with a very minimal amount found in the urine.^[8]

Half life

Ipratropium presents a short half-life of about 1.6 hours.^[3]

Clearance

The average clearance rate of ipratropium is of 2.3 L/min with a renal clearance of 0.9 L/min.^[16]

Toxicity

The reported LD50 in mice after oral administration of ipratropium is 1500 mg/kg.^[MSDS] However, overdosage is not very likely due to the poor absorption of ipratropium.^[Label]

Ipratropium was not shown to present carcinogenesis, teratogenesis not mutagenesis potential and it did not present effects on fertility. The only effect after high administration of ipratropium was a reduction in the conception rate.^[Label]

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
1,10-Phenanthroline	The therapeutic efficacy of Ipratropium can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of Tachycardia can be increased when Ipratropium is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of Tachycardia can be increased when Ipratropium is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of Tachycardia can be increased when Ipratropium is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Ipratropium.
6-Deoxyerythronolide B	The metabolism of Ipratropium can be decreased when combined with 6-Deoxyerythronolide B.
7-ethyl-10-hydroxycamptothecin	The metabolism of Ipratropium can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
7-Nitroindazole	7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Ipratropium.
Abediterol	The risk or severity of Tachycardia can be increased when Ipratropium is combined with Abediterol.
Acepromazine	Acepromazine may increase the central nervous system depressant (CNS depressant) activities of Ipratropium.

Food Interactions

Not Available

References

General References

Rehder KJ: Adjunct Therapies for Refractory Status Asthmaticus in Children. Respir Care. 2017 Jun;62(6):849-865. doi: 10.4187/respcare.05174. [PubMed:28546381]
Seppi K, Weintraub D, Coelho M, Perez-Lloret S, Fox SH, Katzenschlager R, Hametner EM, Poewe W, Rascol O, Goetz CG, Sampaio C: The Movement Disorder Society Evidence-Based Medicine Review Update: Treatments for the non-motor symptoms of Parkinson's disease. Mov Disord. 2011 Oct;26 Suppl 3:S42-80. doi: 10.1002/mds.23884. [PubMed:22021174]
Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]
Osmond MH, Klassen TP: Efficacy of ipratropium bromide in acute childhood asthma: a meta-analysis. Acad Emerg Med. 1995 Jul;2(7):651-6. [PubMed:8521214]
Hockstein NG, Samadi DS, Gendron K, Handler SD: Sialorrhea: a management challenge. Am Fam Physician. 2004 Jun 1;69(11):2628-34. [PubMed:15202698]
Upfal J. (2007). The Australian Drug Guide (7th ed.). National Library of Australia.
George R., Light R., Matthay M. and Matthay R. (2005). Chest Medicine. Essentials of pulmonary and critical care medicine. (5th ed.). Lippincott Williams & Wilkins. [ISBN:978-0-7817-5273-2]
Barnes P., Drazen J., Rennard S. and Thomson N. (2002). Asthma and COPD. Elsevier Science Ltd. [ISBN:0-12-079028-9]
Woo T.M. and Robinson M. (2016). Pharmacotherapeutics for advanced practice nurse prescribers (4th ed.). Davis Company.
Hale T. and Rowe H. (2017). MEdications & mothers' milk (17th ed.). Springer publishing company. [ISBN:978-0-8261-2858-4]
FDA approvals [Link]
FDA approvals [Link]
Journal of Investigational Allergology and Clinical Immunology [Link]
The differential diagnosis of rhinorrhea [Link]
COPD Foundation [Link]
EMC [Link]

External Links

Human Metabolome Database: HMDB0014476
KEGG Compound: C07052
PubChem Compound: 657308
PubChem Substance: 46506138
ChemSpider: 19962157
ChEBI: 46659
ChEMBL: CHEMBL1621597
Therapeutic Targets Database: DNC000806
PharmGKB: PA450082
IUPHAR: 325
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Ipratropium_bromide

ATC Codes

R03BB01 — Ipratropium bromide

R01AX03 — Ipratropium bromide

R03AL01 — Fenoterol and ipratropium bromide

R03AL02 — Salbutamol and ipratropium bromide

AHFS Codes

12:08.08 — Antimuscarinics Antispasmodics

FDA label

Download (88.1 KB)

MSDS

Download (39.9 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Basic Science	Chronic Obstructive Pulmonary Disease (COPD)	1
1	Completed	Diagnostic	Chronic Obstructive Pulmonary Disease (COPD)	1
1	Completed	Treatment	Status Asthmaticus	1
1, 2	Recruiting	Treatment	Exercise Induced Laryngeal Obstruction (EILO)	1
2	Completed	Diagnostic	Lung Diseases, Obstructive	1
2	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	7
2	Completed	Treatment	Parkinson's Disease (PD)	1
2	Not Yet Recruiting	Treatment	Sialorrhea	1
3	Completed	Prevention	Chronic Lung Diseases / Chronic Obstructive Pulmonary Disease (COPD) / Lung Diseases, Obstructive	1
3	Completed	Treatment	Acute Exacerbation of Chronic Obstructive Pulmonary Disease	1
3	Completed	Treatment	Asthma Bronchial	1
3	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	9
3	Completed	Treatment	Familial Dysautonomia	1
3	Terminated	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Completed	Diagnostic	Asthma Bronchial	1
4	Completed	Supportive Care	Chronic Obstructive Pulmonary Disease (COPD) / Sepsis / Shock	1
4	Completed	Treatment	Asthma Acute / Asthma Bronchial / Reactive Airway Exacerbation	1
4	Completed	Treatment	Asthma Bronchial	1
4	Completed	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	10
4	Completed	Treatment	Cold	1
4	Completed	Treatment	Exercise-Induced Bronchoconstriction (EIB)	1
4	Recruiting	Treatment	Acute Exacerbation of Chronic Obstructive Pulmonary Disease / Chronic Obstructive Pulmonary Disease (COPD)	1
4	Recruiting	Treatment	Acute Tracheobronchitis	1
4	Recruiting	Treatment	Asthma Bronchial	1
4	Recruiting	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
4	Terminated	Treatment	Asthma Bronchial	1
4	Unknown Status	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1
Not Available	Completed	Not Available	Chronic Obstructive Pulmonary Disease (COPD)	6
Not Available	Completed	Not Available	Dyspnea / Quadriplegia	1
Not Available	Completed	Not Available	Lung Diseases, Interstitial	1
Not Available	Completed	Not Available	Mild Chronic Obstructive Pulmonary Disease / Physical Activity / Respiratory Symptoms	1
Not Available	Completed	Not Available	Acute Rhinitis	1
Not Available	Completed	Diagnostic	Chronic Obstructive Pulmonary Disease (COPD)	2
Not Available	Completed	Treatment	Acute Lung Injury (ALI) / Anaesthesia therapy / Extravascular Lung Water / Intensive Care, Surgical / Thoracotomy	1
Not Available	Completed	Treatment	Asthma Bronchial	1
Not Available	Completed	Treatment	Bronchitis	1
Not Available	Not Yet Recruiting	Treatment	Asthma Acute / Asthma in Children	1
Not Available	Recruiting	Treatment	Asthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)	1
Not Available	Terminated	Basic Science	Chronic Obstructive Pulmonary Disease (COPD)	1
Not Available	Unknown Status	Diagnostic	Chronic, severe Obstructive Pulmonary Disease / Dyspnea / Moderate Chronic Obstructive Pulmonary Disease	1
Not Available	Unknown Status	Treatment	Chronic Obstructive Pulmonary Disease (COPD)	1

Pharmacoeconomics

Manufacturers

Boehringer ingelheim pharmaceuticals inc
Actavis mid atlantic llc
Bausch and lomb pharmaceuticals inc
Cobalt laboratories inc
Dey lp
Holopack international corp
Landela pharmaceutical
Nephron corp
Novex pharma
Pharmascience inc
Roxane laboratories inc
Teva parenteral medicines inc
Bausch and lomb inc

Packagers

3M Health Care
Apotex Inc.
A-S Medication Solutions LLC
Automatic Liquid Packaging Inc.
Bausch & Lomb Inc.
Boehringer Ingelheim Ltd.
Cardinal Health
Catalent Pharma Solutions
Cipla Ltd.
Cobalt Pharmaceuticals Inc.
Dey Pharma LP
Dispensing Solutions
Diversified Healthcare Services Inc.
Eon Labs
Holopack International Corp.
Ivax Pharmaceuticals
Medisca Inc.
Mylan
Nephron Pharmaceuticals Corp.
Novex Pharma
Pharmedix
Physicians Total Care Inc.
Redpharm Drug
Roxane Labs
Rx Elite
Sifavitor Srl
Teva Pharmaceutical Industries Ltd.
Watson Pharmaceuticals

Dosage forms

Form	Route	Strength
Solution	Respiratory (inhalation)	250 mcg
Aerosol, metered	Respiratory (inhalation)	18 ug/1
Spray, metered	Nasal	21 ug/1
Aerosol, metered	Respiratory (inhalation)	20 mcg
Aerosol	Nasal; Respiratory (inhalation)	20 mcg
Solution	Nasal	21 mcg
Solution	Nasal	42 mcg
Aerosol, metered	Respiratory (inhalation)	17 ug/1
Aerosol, metered	Respiratory (inhalation)
Aerosol, metered	Oral; Respiratory (inhalation)
Spray, metered	Respiratory (inhalation)
Liquid	Respiratory (inhalation)	125 mcg
Liquid	Respiratory (inhalation)	250 mcg
Solution	Oral; Respiratory (inhalation)
Liquid	Respiratory (inhalation)	0.30 mg
Solution	Respiratory (inhalation)	0.5 mg/1mL
Solution	Respiratory (inhalation)	0.5 mg/2.5mL
Solution	Respiratory (inhalation)	500 ug/2.5mL
Spray	Nasal	21 ug/1
Spray	Nasal	42 ug/1
Spray	Respiratory (inhalation)	21 ug/1
Spray	Respiratory (inhalation)	42 ug/1
Spray, metered	Nasal	42 ug/1
Inhalant	Respiratory (inhalation)
Solution	Respiratory (inhalation)
Solution	Respiratory (inhalation)	.25 mg
Liquid	Respiratory (inhalation)	0.25 mg
Solution	Nasal; Respiratory (inhalation)	250 mcg
Solution	Respiratory (inhalation)	125 mcg

Prices

Unit description	Cost	Unit
Atrovent HFA 17 mcg/act Aerosol 12.9 gm Inhaler	143.59USD	inhaler
Ipratropium bromide powder	100.06USD	g
Atrovent 0.03% Solution 30ml Nasal Spray	96.95USD	bottle
Atrovent 0.06% Solution 15ml Nasal Spray	84.68USD	bottle
Ipratropium Bromide 0.03% Solution 30ml Bottle	53.82USD	bottle
Ipratropium Bromide 0.06% Solution 15ml Bottle	46.14USD	bottle
Ipratropium Bromide 0.02% Solution Each Box Contains Twenty-Five 2.5ml Vials	45.86USD	box
Atrovent hfa inhaler	11.89USD	g
Atrovent 0.06% spray	5.33USD	ml
Atrovent 0.03% spray	3.11USD	ml
Ipratropium 0.06% spray	2.96USD	ml
Ipratropium 0.03% spray	1.73USD	ml
Atrovent 0.03 % Spray	1.04USD	ml
Apo-Ipravent 250 mcg/ml Solution	0.58USD	ml
Mylan-Ipratropium 250 mcg/ml Solution	0.58USD	ml
Novo-Ipramide 250 mcg/ml Solution	0.58USD	ml
Pms-Ipratropium 0.03 % Spray	0.58USD	ml
Pms-Ipratropium 250 mcg/ml Solution	0.58USD	ml
Atrovent Hfa 20 mcg/dose Metered Dose Aerosol	0.1USD	metered dose aerosol

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5766573	No	1998-06-16	2009-11-28
CA2151383	No	2005-02-08	2013-12-06
US6632842	No	2003-10-14	2021-12-28
US8474447	No	2013-07-02	2030-01-17
US6739333	No	2004-05-25	2020-05-26
US6983743	No	2006-01-10	2020-05-26
US6453795	Yes	2002-09-24	2017-06-05
US8733341	Yes	2014-05-27	2031-04-16
US9027967	Yes	2015-05-12	2027-10-01
US7104470	Yes	2006-09-12	2017-04-04
US7246615	Yes	2007-07-24	2016-12-01
US7896264	Yes	2011-03-01	2025-11-26
US7988001	Yes	2011-08-02	2022-02-04
US7802568	Yes	2010-09-28	2019-08-26
US6149054	Yes	2000-11-21	2017-06-16
US6726124	Yes	2004-04-27	2017-04-04
US7396341	Yes	2008-07-08	2027-04-10
US6846413	Yes	2005-01-25	2019-02-28
US6176442	Yes	2001-01-23	2016-12-01
US7837235	Yes	2010-11-23	2028-09-13
US5964416	Yes	1999-10-12	2017-04-04
US7284474	Yes	2007-10-23	2025-02-26
US6977042	Yes	2005-12-20	2019-02-28
US6988496	Yes	2006-01-24	2020-08-23

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	230 ºC Decomposes (bromide)	Brittain H. 2003. Profiles of Drug Substances.
boiling point (°C)	Decomposes at 230 ºC	Brittain H. 2003. Profiles of Drug Substances.
water solubility	Freely soluble	Brittain H. 2003. Profiles of Drug Substances.
logP	0.038	Wood C. et al. 1995. J Allergy Clin Immunol.

Predicted Properties

Property	Value	Source
Water Solubility	0.00122 mg/mL	ALOGPS
logP	0.89	ALOGPS
logP	-1.8	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	105.9 m³·mol^-1	ChemAxon
Polarizability	37.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	-	0.9425
Blood Brain Barrier	+	0.8883
Caco-2 permeable	+	0.6619
P-glycoprotein substrate	Substrate	0.5085
P-glycoprotein inhibitor I	Non-inhibitor	0.8489
P-glycoprotein inhibitor II	Non-inhibitor	0.5964
Renal organic cation transporter	Inhibitor	0.6651
CYP450 2C9 substrate	Non-substrate	0.7214
CYP450 2D6 substrate	Non-substrate	0.7637
CYP450 3A4 substrate	Substrate	0.6657
CYP450 1A2 substrate	Non-inhibitor	0.8412
CYP450 2C9 inhibitor	Non-inhibitor	0.9118
CYP450 2D6 inhibitor	Non-inhibitor	0.8915
CYP450 2C19 inhibitor	Non-inhibitor	0.8783
CYP450 3A4 inhibitor	Non-inhibitor	0.9396
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9528
Ames test	Non AMES toxic	0.7112
Carcinogenicity	Non-carcinogens	0.8979
Biodegradation	Ready biodegradable	0.5154
Rat acute toxicity	2.7983 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9596
hERG inhibition (predictor II)	Inhibitor	0.5879

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available

Taxonomy

Classification: Not classified

Targets

Details1. Muscarinic acetylcholine receptor M1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Phosphatidylinositol phospholipase c activity
Specific Function: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name: CHRM1
Uniprot ID: P11229
Uniprot Name: Muscarinic acetylcholine receptor M1
Molecular Weight: 51420.375 Da

References

Wellington K: Ipratropium bromide HFA. Treat Respir Med. 2005;4(3):215-20; discussion 221-2. [PubMed:15987237]
Rehder KJ: Adjunct Therapies for Refractory Status Asthmaticus in Children. Respir Care. 2017 Jun;62(6):849-865. doi: 10.4187/respcare.05174. [PubMed:28546381]
Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]

Details2. Muscarinic acetylcholine receptor M2

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: G-protein coupled acetylcholine receptor activity
Specific Function: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name: CHRM2
Uniprot ID: P08172
Uniprot Name: Muscarinic acetylcholine receptor M2
Molecular Weight: 51714.605 Da

References

Wellington K: Ipratropium bromide HFA. Treat Respir Med. 2005;4(3):215-20; discussion 221-2. [PubMed:15987237]
Rehder KJ: Adjunct Therapies for Refractory Status Asthmaticus in Children. Respir Care. 2017 Jun;62(6):849-865. doi: 10.4187/respcare.05174. [PubMed:28546381]
Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]

Details3. Muscarinic acetylcholine receptor M3

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Receptor activity
Specific Function: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name: CHRM3
Uniprot ID: P20309
Uniprot Name: Muscarinic acetylcholine receptor M3
Molecular Weight: 66127.445 Da

References

Wellington K: Ipratropium bromide HFA. Treat Respir Med. 2005;4(3):215-20; discussion 221-2. [PubMed:15987237]
Rehder KJ: Adjunct Therapies for Refractory Status Asthmaticus in Children. Respir Care. 2017 Jun;62(6):849-865. doi: 10.4187/respcare.05174. [PubMed:28546381]
Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

Details2. alpha1-acid glycoprotein (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: No
Actions: Binder

General Function: Not Available
Specific Function: Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:

Name	UniProt ID
Alpha-1-acid glycoprotein 1	P02763
Alpha-1-acid glycoprotein 2	P19652

Transporters

Details1. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Nakamura T, Nakanishi T, Haruta T, Shirasaka Y, Keogh JP, Tamai I: Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95. doi: 10.1021/mp900206j. [PubMed:20020740]

Details2. Solute carrier family 22 member 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Symporter activity
Specific Function: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name: SLC22A4
Uniprot ID: Q9H015
Uniprot Name: Solute carrier family 22 member 4
Molecular Weight: 62154.48 Da

References

Nakamura T, Nakanishi T, Haruta T, Shirasaka Y, Keogh JP, Tamai I: Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95. doi: 10.1021/mp900206j. [PubMed:20020740]

Drug created on June 13, 2005 07:24 / Updated on April 22, 2019 17:13

Ipratropium

Identification

Structure for Ipratropium (DB00332)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

Carriers

Components:

Transporters

References

References