glycopyrronium bromide indications/contra

Stem definitionDrug idCAS RN
4302 596-51-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sialanar
  • NVA237
  • Seebri Breezhaler
  • glycopyrronium bromide
  • copyrrolate
  • gastrodyn
  • glycopyrrolate
  • robanul
  • glycopyrronium
  • glycopyrrolate bromide
Glycopyrrolate is a long-acting muscarinic antagonist, which is often referred to as an anticholinergic. It has similar affinity to the subtypes of muscarinic receptors M1 to M5. In the airways, it exhibits pharmacological effects through inhibition of M3 receptor at the smooth muscle leading to bronchodilation. The competitive and reversible nature of antagonism was shown with human and animal origin receptors and isolated organ preparations. In preclinical in vitro as well as in vivo studies, prevention of methacholine and acetylcholine induced bronchoconstrictive effects was dose-dependent and lasted longer than 24 hours. The clinical relevance of these findings is unknown. The bronchodilation following inhalation of glycopyrrolate is predominantly a site-specific effect.
  • Molecular weight: 318.44
  • Formula: C19H28NO3
  • CLOGP: 0.12
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -5.57
  • ROTB: 5

Drug dosage:

DoseUnitRoute
3 mg O
0.30 mg P
3 mg R
44 mcg Inhal.powder

Approvals:

DateAgencyCompanyOrphan
Aug. 11, 1961 FDA SHIONOGI INC

FDA Adverse Event Reporting System

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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
Chronic obstructive pulmonary disease 330.97 31.01 76 707 10933 3374143
Dyspnoea 315.30 31.01 120 663 102814 3282262
Cough 250.65 31.01 80 703 39778 3345298
Forced expiratory volume decreased 132.65 31.01 22 761 552 3384524
Asthma 124.86 31.01 36 747 12366 3372710
Malaise 102.60 31.01 48 735 65129 3319947
Emphysema 99.80 31.01 21 762 1947 3383129
Product use issue 99.15 31.01 32 751 15969 3369107
Wheezing 92.37 31.01 26 757 8145 3376931
Product use in unapproved indication 86.45 31.01 21 762 3705 3381371
Pneumonia 84.28 31.01 43 740 70100 3314976
Dyspnoea exertional 82.78 31.01 23 760 6863 3378213
Productive cough 79.89 31.01 22 761 6349 3378727
Chest discomfort 77.03 31.01 27 756 17258 3367818
Tachycardia 76.25 31.01 29 754 23342 3361734
Dyspnoea at rest 75.10 31.01 13 770 421 3384655
Cardiac arrest 61.63 31.01 26 757 27293 3357783
Chest pain 57.97 31.01 28 755 40247 3344829
Cardiac disorder 55.62 31.01 20 763 13699 3371377
Sputum discoloured 55.51 31.01 12 771 1257 3383819
Respiratory failure 55.44 31.01 23 760 23118 3361958
Urinary retention 54.45 31.01 17 766 7555 3377521
Infective exacerbation of chronic obstructive airways disease 53.84 31.01 9 774 235 3384841
Hypertension 53.11 31.01 26 757 38440 3346636
Drug ineffective 52.30 31.01 38 745 116052 3269024
Dry mouth 50.10 31.01 17 766 9805 3375271
Palpitations 49.20 31.01 20 763 19063 3366013
Lung disorder 47.71 31.01 16 767 8901 3376175
Death 45.21 31.01 39 744 152285 3232791
Blood pressure increased 39.78 31.01 18 765 22212 3362864

Pharmacologic Action:

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SourceCodeDescription
ATC A03AB02 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
Synthetic anticholinergics, quaternary ammonium compounds
ATC R03BB06 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
Anticholinergics
ATC A03CA05 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
ANTISPASMODICS IN COMBINATION WITH PSYCHOLEPTICS
Synthetic anticholinergic agents in combination with psycholeptics
ATC R03AL04 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combinations with anticholinergics incl. triple combinations with corticosteroids
ATC R03AL07 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combinations with anticholinergics incl. triple combinations with corticosteroids
ATC R03AL09 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combinations with anticholinergics incl. triple combinations with corticosteroids
MeSH PA D000759 Adjuvants, Anesthesia
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
FDA EPC N0000175574 Anticholinergic

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Peptic ulcer indication 13200003 DOID:750
Chronic obstructive lung disease indication 13645005 DOID:3083
General anesthesia indication 50697003
Excessive salivation indication 53827007
Vagal Reflex Bradycardia indication
Brain damage contraindication 2470005
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Hyperammonemia contraindication 9360008
Hepatic encephalopathy contraindication 13920009 DOID:13413
Severe chronic ulcerative colitis contraindication 14311001
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007 DOID:2848
Hypertensive disorder contraindication 38341003 DOID:10763
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Paralytic ileus contraindication 55525008 DOID:8442
Peptic reflux disease contraindication 57643001 DOID:13976
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Poisoning by phenobarbital contraindication 64921004
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Hepatic coma contraindication 72836002 DOID:12550
Sleep apnea contraindication 73430006 DOID:0050848
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Hiatal hernia contraindication 84089009 DOID:12642
Kidney disease contraindication 90708001 DOID:2527
Myasthenia gravis contraindication 91637004 DOID:437
Gastrointestinal obstruction contraindication 126765001
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Myocardial dysfunction contraindication 233928007
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Pyloric obstruction contraindication 244815007 DOID:3122
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Dyspnea contraindication 267036007
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Drowsy contraindication 271782001
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Angle-closure glaucoma contraindication 392291006 DOID:13550
Gastric ulcer contraindication 397825006 DOID:10808
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Disorder of coronary artery contraindication 414024009
Porphyria contraindication 418470004 DOID:13268
Irritable bowel syndrome off-label use 10743008 DOID:9778
Diarrhea off-label use 62315008

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION 7820694 June 2, 2020 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION 8067437 June 2, 2020 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION 8283362 June 2, 2020 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION 8658673 June 2, 2020 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
15.6MCG/INH SEEBRI SUNOVION PHARMS INC N207923 Oct. 29, 2015 RX POWDER INHALATION 7229607 April 9, 2021 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
15.6MCG/INH SEEBRI SUNOVION PHARMS INC N207923 Oct. 29, 2015 RX POWDER INHALATION 8029768 April 9, 2021 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION 7229607 April 9, 2021 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION 8029768 April 9, 2021 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
1MG/5ML CUVPOSA MERZ PHARMS N022571 July 28, 2010 RX SOLUTION ORAL 7638552 Aug. 20, 2023 REDUCE CHRONIC SEVERE DROOLING (I.E., SIALORRHEA) IN PATIENTS WITH NEUROLOGIC CONDITIONS ASSOCIATED WITH PROBLEM DROOLING
1MG/5ML CUVPOSA MERZ PHARMS N022571 July 28, 2010 RX SOLUTION ORAL 7816396 Aug. 20, 2023 REDUCE CHRONIC SEVERE DROOLING (I.E., SIALORRHEA) IN PATIENTS WITH NEUROLOGIC CONDITIONS ASSOCIATED WITH PROBLEM DROOLING
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION 6878721 Feb. 25, 2025 LONG - TERM MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
0.0090MG/INH BEVESPI AEROSPHERE ASTRAZENECA PHARMS N208294 April 25, 2016 RX AEROSOL, METERED INHALATION 8324266 May 28, 2030 USE IN THE LONG-TERM, MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
0.0090MG/INH BEVESPI AEROSPHERE ASTRAZENECA PHARMS N208294 April 25, 2016 RX AEROSOL, METERED INHALATION 8703806 May 28, 2030 USE IN THE LONG-TERM, MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
0.0090MG/INH BEVESPI AEROSPHERE ASTRAZENECA PHARMS N208294 April 25, 2016 RX AEROSOL, METERED INHALATION 8808713 May 28, 2030 USE IN THE LONG-TERM, MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
0.0090MG/INH BEVESPI AEROSPHERE ASTRAZENECA PHARMS N208294 April 25, 2016 RX AEROSOL, METERED INHALATION 9415009 May 28, 2030 USE IN THE LONG-TERM, MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
0.0090MG/INH BEVESPI AEROSPHERE ASTRAZENECA PHARMS N208294 April 25, 2016 RX AEROSOL, METERED INHALATION 9463161 May 28, 2030 USE IN THE LONG-TERM, MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)
0.0090MG/INH BEVESPI AEROSPHERE ASTRAZENECA PHARMS N208294 April 25, 2016 RX AEROSOL, METERED INHALATION 8815258 March 17, 2031 USE IN THE LONG-TERM, MAINTENANCE TREATMENT OF AIRFLOW OBSTRUCTION IN PATIENTS WITH CHRONIC OBSTRUCTIVE PULMONARY DISEASE (COPD)

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
15.6MCG/INH SEEBRI SUNOVION PHARMS INC N207923 Oct. 29, 2015 RX POWDER INHALATION Oct. 29, 2018 NEW PRODUCT
15.6MCG/INH UTIBRON SUNOVION PHARMS INC N207930 Oct. 29, 2015 RX POWDER INHALATION Oct. 29, 2018 NEW PRODUCT
0.0090MG/INH BEVESPI AEROSPHERE ASTRAZENECA PHARMS N208294 April 25, 2016 RX AEROSOL, METERED INHALATION April 25, 2019 NEW PRODUCT
25MCG/ML LONHALA MAGNAIR KIT SUNOVION RESP N208437 Dec. 5, 2017 RX SOLUTION INHALATION Dec. 5, 2020 NEW PRODUCT

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 9.69 SCIENTIFIC LITERATURE CHEMBL
Muscarinic acetylcholine receptor M2 GPCR ANTAGONIST Ki 9.25 SCIENTIFIC LITERATURE IUPHAR
Muscarinic acetylcholine receptor M3 GPCR ANTAGONIST Ki 9.64 SCIENTIFIC LITERATURE CHEMBL
Muscarinic acetylcholine receptor M4 GPCR ANTAGONIST Ki 9.06 SCIENTIFIC LITERATURE IUPHAR
Muscarinic acetylcholine receptor M5 GPCR ANTAGONIST Ki 8.91 SCIENTIFIC LITERATURE IUPHAR

External reference:

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IDSource
7459 IUPHAR_LIGAND_ID
4018421 VUID
N0000146747 NUI
C0017970 UMLSCUI
D00540 KEGG_DRUG
DB00986 DRUGBANK_ID
CHEMBL1201027 ChEMBL_ID
CHEMBL1201335 ChEMBL_ID
D006024 MESH_DESCRIPTOR_UI
22168005 SNOMEDCT_US
387122008 SNOMEDCT_US
N0000005922 NDFRT
11693 PUBCHEM_CID
V92SO9WP2I UNII
1038 INN_ID
51186-83-5 SECONDARY_CAS_RN
CHEBI:90972 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
SEEBRI NEOHALER HUMAN PRESCRIPTION DRUG LABEL 1 0078-0662 CAPSULE 15.60 ug RESPIRATORY (INHALATION) NDA 18 sections
UTIBRON NEOHALER HUMAN PRESCRIPTION DRUG LABEL 2 0078-0664 CAPSULE 15.60 ug RESPIRATORY (INHALATION) NDA 19 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-1250 TABLET 1 mg ORAL ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-1251 TABLET 2 mg ORAL ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9584 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9585 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9586 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9587 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9679 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9680 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9681 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9682 INJECTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Cuvposa HUMAN PRESCRIPTION DRUG LABEL 1 0259-0501 LIQUID 1 mg ORAL NDA 18 sections
BEVESPI AEROSPHERE HUMAN PRESCRIPTION DRUG LABEL 2 0310-4600 AEROSOL, METERED 9 ug RESPIRATORY (INHALATION) NDA 19 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0517-4601 INJECTION, SOLUTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0517-4602 INJECTION, SOLUTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0517-4605 INJECTION, SOLUTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0517-4620 INJECTION, SOLUTION 0.20 mg INTRAMUSCULAR ANDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6033 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6034 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6035 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6036 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Robinul HUMAN PRESCRIPTION DRUG LABEL 1 0641-6104 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Robinul HUMAN PRESCRIPTION DRUG LABEL 1 0641-6105 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Robinul HUMAN PRESCRIPTION DRUG LABEL 1 0641-6106 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Robinul HUMAN PRESCRIPTION DRUG LABEL 1 0641-6107 INJECTION 0.20 mg INTRAMUSCULAR NDA 12 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0722-7097 TABLET 1.50 mg ORAL ANDA 11 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6521 TABLET 1 mg ORAL ANDA 16 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 13107-014 TABLET 1 mg ORAL ANDA 11 sections
Glycopyrrolate HUMAN PRESCRIPTION DRUG LABEL 1 23155-606 TABLET 1 mg ORAL ANDA 10 sections