Identification

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Name
Ipratropium
Accession Number
DB00332  (APRD00537)
Type
Small Molecule
Groups
Approved, Experimental
Description

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
Thumb
Synonyms
  • bromuro de ipratropio
  • Ipratropium cation
  • Ipratropium ion
Product Ingredients
IngredientUNIICASInChI Key
Ipratropium bromide anhydrousVJV4X1P2Z122254-24-6LHLMOSXCXGLMMN-WDTICOSOSA-M
Ipratropium bromide monohydrateJ697UZ2A9J66985-17-9KEWHKYJURDBRMN-XSAPEOHZSA-M
Ipratropium chlorideNot AvailableNot AvailableMQIPRYDNKGFOGV-WDTICOSOSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AtroventSpray, metered21 ug/1NasalPhysicians Total Care, Inc.2006-03-31Not applicableUs
AtroventSolution250 mcgRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1988-12-312007-10-11Canada
AtroventSpray, metered21 ug/1NasalBoehringer Ingelheim Pharmaceuticals, Inc.1996-01-012018-12-01Us
AtroventSpray, metered42 ug/1NasalBoehringer Ingelheim Pharmaceuticals, Inc.1996-01-012018-12-01Us
AtroventSpray, metered42 ug/1NasalRemedy Repack2018-03-142018-03-14Us
AtroventAerosol, metered17 ug/1Respiratory (inhalation)Physicians Total Care, Inc.1995-08-072006-01-20Us
AtroventAerosol, metered18 ug/1Respiratory (inhalation)Boehringer Ingelheim1986-12-192006-06-02Us
AtroventSpray, metered42 ug/1NasalPhysicians Total Care, Inc.2003-05-232011-06-30Us
Atrovent HFAAerosol, metered20 mcgRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee2004-03-24Not applicableCanada
Atrovent HFAAerosol, metered17 ug/1Respiratory (inhalation)Rpk Pharmaceuticals, Inc.2005-05-01Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ipravent Solution - Inh 250mcg/mlSolution250 mcgRespiratory (inhalation)Apotex Corporation1994-12-31Not applicableCanada
Apo-ipravent SterulesSolution125 mcgRespiratory (inhalation)Apotex Corporation2001-08-28Not applicableCanada
Apo-ipravent SterulesSolution250 mcgRespiratory (inhalation)Apotex Corporation1998-07-09Not applicableCanada
Dom-ipratropiumSolution21 mcgNasalDominion Pharmacal1999-09-15Not applicableCanada
Dom-ipratropium 125 Mcg/mlLiquid125 mcgRespiratory (inhalation)Dominion PharmacalNot applicableNot applicableCanada
Dom-ipratropium 250 Mcg/ml (1 Ml)Liquid250 mcgRespiratory (inhalation)Dominion PharmacalNot applicableNot applicableCanada
Dom-ipratropium 250 Mcg/ml (2 Ml)Liquid250 mcgRespiratory (inhalation)Dominion PharmacalNot applicableNot applicableCanada
Dom-ipratropium 250 Mcg/ml (20 Ml)Liquid250 mcgRespiratory (inhalation)Dominion PharmacalNot applicableNot applicableCanada
Ipratropium BromideSpray, metered42 ug/1NasalApotex Corporation2003-04-182011-05-19Us
Ipratropium bromideSpray, metered21 ug/1NasalBausch & Lomb Incorporated2003-03-31Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-salvent-ipravent SterulesIpratropium bromide monohydrate (0.5 mg) + Salbutamol (2.5 mg)SolutionRespiratory (inhalation)Apotex Corporation2006-08-25Not applicableCanada
CombiventIpratropium bromide monohydrate (18 ug/1) + Salbutamol sulfate (90 ug/1)Aerosol, meteredRespiratory (inhalation)Physicians Total Care, Inc.2000-09-182013-06-30Us
CombiventIpratropium bromide monohydrate (18 ug/1) + Salbutamol sulfate (90 ug/1)Aerosol, meteredRespiratory (inhalation)Boehringer Ingelheim1997-06-012014-09-30Us
Combivent Inhalation AerosolIpratropium bromide monohydrate (20 mcg) + Salbutamol sulfate (120 mcg)Aerosol, meteredOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1995-12-312007-10-02Canada
Combivent RespimatIpratropium bromide monohydrate (20 ug/1) + Salbutamol sulfate (120 ug/1)Spray, meteredRespiratory (inhalation)Boehringer Ingelheim2012-07-01Not applicableUs
Combivent RespimatIpratropium bromide monohydrate (20 mcg) + Salbutamol (100 mcg)SolutionRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee2014-09-16Not applicableCanada
Combivent UdvIpratropium bromide monohydrate (0.2 mg) + Salbutamol (1 mg)SolutionRespiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1997-07-25Not applicableCanada
DuoNebIpratropium bromide monohydrate (0.5 mg/3mL) + Salbutamol sulfate (2.5 mg/3mL)SolutionRespiratory (inhalation)Physicians Total Care, Inc.2007-06-062012-06-30Us
DuoNebIpratropium bromide monohydrate (0.5 mg/3mL) + Salbutamol sulfate (2.5 mg/3mL)SolutionRespiratory (inhalation)Mylan Specialty2011-02-152014-06-30Us
Duovent UdvIpratropium bromide monohydrate (0.125 mg) + Fenoterol hydrobromide (0.3125 mg)SolutionOral; Respiratory (inhalation)Boehringer Ingelheim (Canada) Ltd Ltee1995-12-312017-01-31Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ipratropium BromideIpratropium bromide monohydrate (0.5 mg/1mL)SolutionRespiratory (inhalation)Cantrell Drug Company2012-10-122015-01-14Us
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]

TargetActionsOrganism
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
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Ipratropium can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of Tachycardia can be increased when Ipratropium is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of Tachycardia can be increased when Ipratropium is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of Tachycardia can be increased when Ipratropium is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Ipratropium.
6-Deoxyerythronolide BThe metabolism of Ipratropium can be decreased when combined with 6-Deoxyerythronolide B.
7-ethyl-10-hydroxycamptothecinThe metabolism of Ipratropium can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
7-Nitroindazole7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Ipratropium.
AbediterolThe risk or severity of Tachycardia can be increased when Ipratropium is combined with Abediterol.
AcepromazineAcepromazine may increase the central nervous system depressant (CNS depressant) activities of Ipratropium.
Food Interactions
Not Available

References

General References
  1. 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]
  2. 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]
  3. Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]
  4. 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]
  5. Hockstein NG, Samadi DS, Gendron K, Handler SD: Sialorrhea: a management challenge. Am Fam Physician. 2004 Jun 1;69(11):2628-34. [PubMed:15202698]
  6. Upfal J. (2007). The Australian Drug Guide (7th ed.). National Library of Australia.
  7. 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]
  8. Barnes P., Drazen J., Rennard S. and Thomson N. (2002). Asthma and COPD. Elsevier Science Ltd. [ISBN:0-12-079028-9]
  9. Woo T.M. and Robinson M. (2016). Pharmacotherapeutics for advanced practice nurse prescribers (4th ed.). Davis Company.
  10. Hale T. and Rowe H. (2017). MEdications & mothers' milk (17th ed.). Springer publishing company. [ISBN:978-0-8261-2858-4]
  11. FDA approvals [Link]
  12. FDA approvals [Link]
  13. Journal of Investigational Allergology and Clinical Immunology [Link]
  14. The differential diagnosis of rhinorrhea [Link]
  15. COPD Foundation [Link]
  16. 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 bromideR01AX03 — Ipratropium bromideR03AL01 — Fenoterol and ipratropium bromideR03AL02 — 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
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
1CompletedDiagnosticChronic Obstructive Pulmonary Disease (COPD)1
1CompletedTreatmentStatus Asthmaticus1
1, 2RecruitingTreatmentExercise Induced Laryngeal Obstruction (EILO)1
2CompletedDiagnosticLung Diseases, Obstructive1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)7
2CompletedTreatmentParkinson's Disease (PD)1
2Not Yet RecruitingTreatmentSialorrhea1
3CompletedPreventionChronic Lung Diseases / Chronic Obstructive Pulmonary Disease (COPD) / Lung Diseases, Obstructive1
3CompletedTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease1
3CompletedTreatmentAsthma Bronchial1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)9
3CompletedTreatmentFamilial Dysautonomia1
3TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedDiagnosticAsthma Bronchial1
4CompletedSupportive CareChronic Obstructive Pulmonary Disease (COPD) / Sepsis / Shock1
4CompletedTreatmentAsthma Acute / Asthma Bronchial / Reactive Airway Exacerbation1
4CompletedTreatmentAsthma Bronchial1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)10
4CompletedTreatmentCold1
4CompletedTreatmentExercise-Induced Bronchoconstriction (EIB)1
4RecruitingTreatmentAcute Exacerbation of Chronic Obstructive Pulmonary Disease / Chronic Obstructive Pulmonary Disease (COPD)1
4RecruitingTreatmentAcute Tracheobronchitis1
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4TerminatedTreatmentAsthma Bronchial1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedNot AvailableChronic Obstructive Pulmonary Disease (COPD)6
Not AvailableCompletedNot AvailableDyspnea / Quadriplegia1
Not AvailableCompletedNot AvailableLung Diseases, Interstitial1
Not AvailableCompletedNot AvailableMild Chronic Obstructive Pulmonary Disease / Physical Activity / Respiratory Symptoms1
Not AvailableCompletedNot AvailableAcute Rhinitis1
Not AvailableCompletedDiagnosticChronic Obstructive Pulmonary Disease (COPD)2
Not AvailableCompletedTreatmentAcute Lung Injury (ALI) / Anaesthesia therapy / Extravascular Lung Water / Intensive Care, Surgical / Thoracotomy1
Not AvailableCompletedTreatmentAsthma Bronchial1
Not AvailableCompletedTreatmentBronchitis1
Not AvailableNot Yet RecruitingTreatmentAsthma Acute / Asthma in Children1
Not AvailableRecruitingTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
Not AvailableTerminatedBasic ScienceChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableUnknown StatusDiagnosticChronic, severe Obstructive Pulmonary Disease / Dyspnea / Moderate Chronic Obstructive Pulmonary Disease1
Not AvailableUnknown StatusTreatmentChronic 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
FormRouteStrength
SolutionRespiratory (inhalation)250 mcg
Aerosol, meteredRespiratory (inhalation)18 ug/1
Spray, meteredNasal21 ug/1
Aerosol, meteredRespiratory (inhalation)20 mcg
AerosolNasal; Respiratory (inhalation)20 mcg
SolutionNasal21 mcg
SolutionNasal42 mcg
Aerosol, meteredRespiratory (inhalation)17 ug/1
Aerosol, meteredRespiratory (inhalation)
Aerosol, meteredOral; Respiratory (inhalation)
Spray, meteredRespiratory (inhalation)
LiquidRespiratory (inhalation)125 mcg
LiquidRespiratory (inhalation)250 mcg
SolutionOral; Respiratory (inhalation)
LiquidRespiratory (inhalation)0.30 mg
SolutionRespiratory (inhalation)0.5 mg/1mL
SolutionRespiratory (inhalation)0.5 mg/2.5mL
SolutionRespiratory (inhalation)500 ug/2.5mL
SprayNasal21 ug/1
SprayNasal42 ug/1
SprayRespiratory (inhalation)21 ug/1
SprayRespiratory (inhalation)42 ug/1
Spray, meteredNasal42 ug/1
InhalantRespiratory (inhalation)
SolutionRespiratory (inhalation)
SolutionRespiratory (inhalation).25 mg
LiquidRespiratory (inhalation)0.25 mg
SolutionNasal; Respiratory (inhalation)250 mcg
SolutionRespiratory (inhalation)125 mcg
Prices
Unit descriptionCostUnit
Atrovent HFA 17 mcg/act Aerosol 12.9 gm Inhaler143.59USD inhaler
Ipratropium bromide powder100.06USD g
Atrovent 0.03% Solution 30ml Nasal Spray96.95USD bottle
Atrovent 0.06% Solution 15ml Nasal Spray84.68USD bottle
Ipratropium Bromide 0.03% Solution 30ml Bottle53.82USD bottle
Ipratropium Bromide 0.06% Solution 15ml Bottle46.14USD bottle
Ipratropium Bromide 0.02% Solution Each Box Contains Twenty-Five 2.5ml Vials45.86USD box
Atrovent hfa inhaler11.89USD g
Atrovent 0.06% spray5.33USD ml
Atrovent 0.03% spray3.11USD ml
Ipratropium 0.06% spray2.96USD ml
Ipratropium 0.03% spray1.73USD ml
Atrovent 0.03 % Spray1.04USD ml
Apo-Ipravent 250 mcg/ml Solution0.58USD ml
Mylan-Ipratropium 250 mcg/ml Solution0.58USD ml
Novo-Ipramide 250 mcg/ml Solution0.58USD ml
Pms-Ipratropium 0.03 % Spray0.58USD ml
Pms-Ipratropium 250 mcg/ml Solution0.58USD ml
Atrovent Hfa 20 mcg/dose Metered Dose Aerosol0.1USD metered dose aerosol
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5766573No1998-06-162009-11-28Us
CA2151383No2005-02-082013-12-06Canada
US6632842No2003-10-142021-12-28Us
US8474447No2013-07-022030-01-17Us
US6739333No2004-05-252020-05-26Us
US6983743No2006-01-102020-05-26Us
US6453795Yes2002-09-242017-06-05Us
US8733341Yes2014-05-272031-04-16Us
US9027967Yes2015-05-122027-10-01Us
US7104470Yes2006-09-122017-04-04Us
US7246615Yes2007-07-242016-12-01Us
US7896264Yes2011-03-012025-11-26Us
US7988001Yes2011-08-022022-02-04Us
US7802568Yes2010-09-282019-08-26Us
US6149054Yes2000-11-212017-06-16Us
US6726124Yes2004-04-272017-04-04Us
US7396341Yes2008-07-082027-04-10Us
US6846413Yes2005-01-252019-02-28Us
US6176442Yes2001-01-232016-12-01Us
US7837235Yes2010-11-232028-09-13Us
US5964416Yes1999-10-122017-04-04Us
US7284474Yes2007-10-232025-02-26Us
US6977042Yes2005-12-202019-02-28Us
US6988496Yes2006-01-242020-08-23Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)230 ºC Decomposes (bromide)Brittain H. 2003. Profiles of Drug Substances.
boiling point (°C)Decomposes at 230 ºCBrittain H. 2003. Profiles of Drug Substances.
water solubilityFreely solubleBrittain H. 2003. Profiles of Drug Substances.
logP0.038Wood C. et al. 1995. J Allergy Clin Immunol.
Predicted Properties
PropertyValueSource
Water Solubility0.00122 mg/mLALOGPS
logP0.89ALOGPS
logP-1.8ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.9 m3·mol-1ChemAxon
Polarizability37.57 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9425
Blood Brain Barrier+0.8883
Caco-2 permeable+0.6619
P-glycoprotein substrateSubstrate0.5085
P-glycoprotein inhibitor INon-inhibitor0.8489
P-glycoprotein inhibitor IINon-inhibitor0.5964
Renal organic cation transporterInhibitor0.6651
CYP450 2C9 substrateNon-substrate0.7214
CYP450 2D6 substrateNon-substrate0.7637
CYP450 3A4 substrateSubstrate0.6657
CYP450 1A2 substrateNon-inhibitor0.8412
CYP450 2C9 inhibitorNon-inhibitor0.9118
CYP450 2D6 inhibitorNon-inhibitor0.8915
CYP450 2C19 inhibitorNon-inhibitor0.8783
CYP450 3A4 inhibitorNon-inhibitor0.9396
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9528
Ames testNon AMES toxic0.7112
CarcinogenicityNon-carcinogens0.8979
BiodegradationReady biodegradable0.5154
Rat acute toxicity2.7983 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9596
hERG inhibition (predictor II)Inhibitor0.5879
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

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
  1. Wellington K: Ipratropium bromide HFA. Treat Respir Med. 2005;4(3):215-20; discussion 221-2. [PubMed:15987237]
  2. 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]
  3. Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]
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
  1. Wellington K: Ipratropium bromide HFA. Treat Respir Med. 2005;4(3):215-20; discussion 221-2. [PubMed:15987237]
  2. 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]
  3. Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]
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
  1. Wellington K: Ipratropium bromide HFA. Treat Respir Med. 2005;4(3):215-20; discussion 221-2. [PubMed:15987237]
  2. 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]
  3. Almadhoun K, Sharma S: Bronchodilators . [PubMed:30085570]

Carriers

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
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:

Transporters

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
  1. 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]
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
  1. 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