ipratropium Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
atropine derivatives 1475 60205-81-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ipratropium
  • ipratropium bromide
  • ipratropium bromide hydrate
  • ipratropium bromide monohydrate
A muscarinic antagonist structurally related to ATROPINE but often considered safer and more effective for inhalation use. It is used for various bronchial disorders, in rhinitis, and as an antiarrhythmic.
  • Molecular weight: 332.46
  • Formula: C20H30NO3
  • CLOGP: -2.19
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -5.48
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.24 mg N
0.12 mg Inhal.aerosol
0.12 mg Inhal.powder
0.30 mg Inhal.solution

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.01 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 3 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 5.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 31.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.95 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.64 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 29, 1986 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Asthma 536.68 34.90 122 777 11192 2345994
Dyspnoea 364.31 34.90 139 760 78594 2278592
Wheezing 253.54 34.90 60 839 6324 2350862
Obstructive airways disorder 232.88 34.90 43 856 1330 2355856
Pneumonia 172.72 34.90 72 827 49224 2307962
Chronic obstructive pulmonary disease 157.86 34.90 42 857 7035 2350151
Drug ineffective 142.28 34.90 79 820 101545 2255641
Cough 138.27 34.90 55 844 33062 2324124
Blood count abnormal 125.24 34.90 28 871 2254 2354932
Lactic acidosis 106.29 34.90 29 870 5301 2351885
Lung hyperinflation 101.25 34.90 15 884 109 2357077
Infective exacerbation of chronic obstructive airways disease 96.17 34.90 15 884 159 2357027
PCO2 increased 95.17 34.90 15 884 171 2357015
Hyperkalaemia 94.34 34.90 27 872 5866 2351320
Blood pH decreased 93.52 34.90 17 882 474 2356712
Blood lactic acid increased 90.18 34.90 18 881 833 2356353
Off label use 88.30 34.90 52 847 73546 2283640
PO2 decreased 87.04 34.90 15 884 305 2356881
Influenza B virus test positive 85.71 34.90 11 888 21 2357165
Oxygen saturation decreased 83.38 34.90 26 873 7560 2349626
Airway peak pressure increased 82.46 34.90 11 888 32 2357154
Blood bicarbonate decreased 80.27 34.90 15 884 488 2356698
Productive cough 78.99 34.90 23 876 5298 2351888
Dyspnoea exertional 77.35 34.90 23 876 5697 2351489
Bronchospasm 77.08 34.90 20 879 3004 2354182
Therapeutic product effect incomplete 75.00 34.90 26 873 10505 2346681
Respiratory rate increased 74.36 34.90 17 882 1503 2355683
Respiratory acidosis 72.93 34.90 15 884 806 2356380
Hypercapnia 72.64 34.90 14 885 538 2356648
Condition aggravated 67.48 34.90 33 866 31946 2325240
Tachycardia 67.23 34.90 27 872 16382 2340804
Acute kidney injury 62.25 34.90 30 869 28092 2329094
Cyanosis 61.87 34.90 17 882 3168 2354018
Tremor 61.22 34.90 27 872 20634 2336552
Status asthmaticus 60.81 34.90 10 889 151 2357035
Seizure 59.94 34.90 28 871 24438 2332748
Atrial fibrillation 57.56 34.90 23 876 13745 2343441
Muscular weakness 55.80 34.90 23 876 14874 2342312
Drug hypersensitivity 53.15 34.90 32 867 46611 2310575
Chest discomfort 52.85 34.90 22 877 14573 2342613
Hypertension 51.04 34.90 26 873 27335 2329851
Neutropenia 50.71 34.90 24 875 21524 2335662
Type 2 diabetes mellitus 48.63 34.90 13 886 2181 2355005
Nausea 45.10 34.90 41 858 112148 2245038
Product quality issue 44.91 34.90 18 881 10811 2346375
Blood test abnormal 44.88 34.90 11 888 1307 2355879
Acute respiratory failure 44.44 34.90 13 886 3025 2354161
Pruritus 42.38 34.90 27 872 43313 2313873
Pupils unequal 42.10 34.90 8 891 284 2356902
Angle closure glaucoma 40.03 34.90 9 890 735 2356451
Hyper IgE syndrome 39.50 34.90 5 894 8 2357178
Tachypnoea 39.15 34.90 11 888 2218 2354968
Lymphocyte count decreased 38.87 34.90 12 887 3351 2353835
Neutrophil count decreased 38.29 34.90 14 885 6553 2350633
Urinary retention 37.85 34.90 12 887 3655 2353531
Respiratory failure 37.82 34.90 17 882 13511 2343675
Drug reaction with eosinophilia and systemic symptoms 36.81 34.90 13 886 5505 2351681
Emphysema 36.65 34.90 9 890 1076 2356110
Cardiac arrest 36.22 34.90 17 882 14913 2342273
Erythema 35.84 34.90 20 879 25139 2332047
Leukopenia 35.63 34.90 15 884 10181 2347005
Pancoast's syndrome 35.42 34.90 4 895 0 2357186
Toxic epidermal necrolysis 35.41 34.90 11 888 3133 2354053

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dyspnoea 279.89 37.50 112 637 51947 1694085
Asthma 271.57 37.50 64 685 4840 1741192
Chronic obstructive pulmonary disease 209.24 37.50 54 695 5899 1740133
Wheezing 113.64 37.50 31 718 4122 1741910
Drug ineffective 105.89 37.50 62 687 63739 1682293
Pupils unequal 100.55 37.50 17 732 219 1745813
Oxygen saturation decreased 82.69 37.50 26 723 5649 1740383
Obstructive airways disorder 80.29 37.50 18 731 1056 1744976
Blood count abnormal 74.83 37.50 18 731 1439 1744593
Cough 70.39 37.50 32 717 19165 1726867
Tachypnoea 66.23 37.50 18 731 2340 1743692
Therapeutic product effect incomplete 63.15 37.50 21 728 5427 1740605
Condition aggravated 61.33 37.50 30 719 21120 1724912
Pneumonia 58.52 37.50 38 711 46144 1699888
Productive cough 54.51 37.50 17 732 3574 1742458
Sputum discoloured 54.15 37.50 12 737 665 1745367
Chest discomfort 53.37 37.50 20 729 7311 1738721
Tachycardia 52.42 37.50 23 726 12605 1733427
Off label use 46.95 37.50 31 718 38540 1707492
Hyperkaliuria 46.14 37.50 6 743 8 1746024
Bronchiectasis 45.13 37.50 10 739 553 1745479
Tachycardia foetal 44.73 37.50 7 742 53 1745979
Oedema peripheral 41.84 37.50 21 728 15529 1730503
Arrhythmia 38.66 37.50 15 734 6001 1740031
Medication error 38.38 37.50 14 735 4729 1741303
Thrombocytopenia 38.34 37.50 22 727 21227 1724805
Confusional state 38.32 37.50 22 727 21256 1724776
Cholestasis 37.96 37.50 13 736 3652 1742380

Pharmacologic Action:

SourceCodeDescription
ATC R01AX03 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Other nasal preparations
ATC R03AL01 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
ATC R03AL02 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
ATC R03BB01 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
Anticholinergics
FDA EPC N0000175574 Anticholinergic
MeSH PA D018927 Anti-Asthmatic Agents
MeSH PA D001993 Bronchodilator Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D019141 Respiratory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bronchospasm indication 4386001
Chronic obstructive lung disease indication 13645005 DOID:3083
Bronchitis indication 32398004 DOID:6132
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Pulmonary emphysema indication 87433001
Chronic Obstructive Pulmonary Disease with Bronchospasms indication
Asthma off-label use 195967001 DOID:2841
Asthma-chronic obstructive pulmonary disease overlap syndrome off-label use 10692761000119107
Ocular hypertension contraindication 4210003 DOID:9282
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Ketoacidosis contraindication 56051008
Metabolic acidosis contraindication 59455009
Diabetes mellitus contraindication 73211009 DOID:9351
Paradoxical bronchospasm contraindication 102578005
Prolonged QT interval contraindication 111975006
Seizure disorder contraindication 128613002
Bladder outflow obstruction contraindication 236645006
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Myocardial ischemia contraindication 414795007 DOID:3393
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.24 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.017% **Federal Register determination that product was not discontinued or withdrawn for safety or efficacy reasons** DUONEB MYLAN SPECIALITY LP N020950 March 21, 2001 DISCN SOLUTION INHALATION 6632842 Dec. 28, 2021 TREATMENT OF BRONCHOSPASM ASSOCIATED WITH COPD IN PATIENTS REQUIRING MORE THAN ONE BRONCHO DILATOR

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M3 GPCR ANTAGONIST Ki 9.29 WOMBAT-PK CHEMBL
Solute carrier family 22 member 2 Transporter IC50 4.82 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR Ki 8.77 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR Ki 9.18 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 8.82 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 9.31 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 9.54 CHEMBL
Muscarinic acetylcholine receptor M3 GPCR Ki 9.74 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 9.11 CHEMBL

External reference:

IDSource
4019791 VUID
N0000147880 NUI
C0027235 UMLSCUI
D02212 KEGG_DRUG
108624006 SNOMEDCT_US
4019791 VANDF
7213 RXNORM
372518007 SNOMEDCT_US
d00265 MMSL
004943 NDDF
DB00332 DRUGBANK_ID
J697UZ2A9J UNII
66985-17-9 SECONDARY_CAS_RN
X8M PDB_CHEM_ID
CHEBI:5956 CHEBI
657309 PUBCHEM_CID
CHEMBL1464005 ChEMBL_ID
D009241 MESH_DESCRIPTOR_UI
CHEMBL1621597 ChEMBL_ID
CHEMBL2134724 ChEMBL_ID
325 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ipratropium Bromide HUMAN PRESCRIPTION DRUG LABEL 1 0781-7157 SOLUTION 0.50 mg RESPIRATORY (INHALATION) ANDA 13 sections
Ipratropium Bromide HUMAN PRESCRIPTION DRUG LABEL 1 21695-911 SOLUTION 0.50 mg RESPIRATORY (INHALATION) ANDA 13 sections
Ipratropium Bromide HUMAN PRESCRIPTION DRUG LABEL 1 42254-041 SOLUTION 0.50 mg RESPIRATORY (INHALATION) ANDA 12 sections
Ipratropium Bromide HUMAN PRESCRIPTION DRUG LABEL 1 42254-355 SPRAY, METERED 42 ug NASAL ANDA 13 sections
Ipratropium Bromide HUMAN PRESCRIPTION DRUG LABEL 1 54868-4082 SOLUTION 0.50 mg RESPIRATORY (INHALATION) ANDA 13 sections
Ipratropium Bromide HUMAN PRESCRIPTION DRUG LABEL 1 54868-5049 SPRAY, METERED 42 ug NASAL ANDA 13 sections
AtroventHFA HUMAN PRESCRIPTION DRUG LABEL 1 54868-5511 AEROSOL, METERED 17 ug RESPIRATORY (INHALATION) NDA 14 sections
Atrovent HUMAN PRESCRIPTION DRUG LABEL 1 54868-5565 SPRAY, METERED 21 ug NASAL NDA 14 sections
Ipratropium Bromide HUMAN PRESCRIPTION DRUG LABEL 1 54868-5751 SPRAY, METERED 21 ug NASAL ANDA 12 sections
Ipratropium Bromide and Albuterol Sulfate HUMAN PRESCRIPTION DRUG LABEL 2 54868-5974 SOLUTION 0.50 mg RESPIRATORY (INHALATION) NDA 12 sections