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    Technical details about Glycopyrrolate, learn more about the structure, uses, toxicity, action, side effects and more

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    Glycopyrrolate

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    2D Structure
    Also known as: 596-51-0, Glycopyrrolate bromide, Robinul, Glycopyrronium bromide, Gastrodyn, Nodapton
    Molecular Formula
    C19H28BrNO3
    Molecular Weight
    398.3  g/mol
    InChI Key
    VPNYRYCIDCJBOM-UHFFFAOYSA-M
    A muscarinic antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide
    2.1.2 InChI
    InChI=1S/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1
    2.1.3 InChI Key
    VPNYRYCIDCJBOM-UHFFFAOYSA-M
    2.1.4 Canonical SMILES
    C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Bromide, Glycopyrronium

    2. Glycopyrronium

    3. Glycopyrronium Bromide

    4. Nva 237

    5. Nva-237

    6. Nva237

    7. Pyrrolidinium, 3-((cyclopentylhydroxyphenylacetyl)oxy)-1,1-dimethyl-, Bromide

    2.2.2 Depositor-Supplied Synonyms

    1. 596-51-0

    2. Glycopyrrolate Bromide

    3. Robinul

    4. Glycopyrronium Bromide

    5. Gastrodyn

    6. Nodapton

    7. Tarodyl

    8. Tarodyn

    9. Asecryl

    10. Cuvposa

    11. Glycopyrronii Bromidum

    12. Robanul

    13. Ahr-504

    14. Bromuro De Glicopirronio

    15. Bromure De Glycopyrronium

    16. Nva-237

    17. Robinal

    18. Seebri Neohaler

    19. 3-hydroxy-1,1-dimethylpyrrolidinium Bromide Alpha-cyclopentylmandelate

    20. Seebri

    21. 1,1-dimethyl-3-hydroxypyrrolidinium Bromide Alpha-cyclopentylmandelate

    22. 1-methyl-3-pyrrolidyl Alpha-phenylcyclopentaneglycolate Methobromide

    23. 3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidin-1-ium Bromide

    24. Pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-,bromide

    25. Ad-237

    26. Pt-001

    27. Nsc-250836

    28. Nsc-251251

    29. Nsc-251252

    30. Copyrrolate

    31. Dsstox_cid_3109

    32. 3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium Bromide

    33. (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate Bromide

    34. Dsstox_rid_76878

    35. Dsstox_gsid_23109

    36. Glycopyrronium (bromide);glycopyrrolate (bromide)

    37. Nva237

    38. Robinul Forte

    39. Pyrrolidinium,1-dimethyl-, Bromide

    40. Seebri Breezhaler

    41. 53808-86-9

    42. (1,1-dimethylpyrrolidin-1-ium-3-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide

    43. Smr000469282

    44. Glycopyrrolate, Erythro-

    45. Nsc 250836

    46. Nsc 251251

    47. Nsc 251252

    48. Org-nc-45

    49. Nsc250836

    50. Nsc251251

    51. Nsc251252

    52. (2s,3's)-glycopyrrolate

    53. Ahr 504

    54. Glycopyrronium (as Bromide)

    55. Nva 237

    56. Glycopyrronii Bromidum [inn-latin]

    57. Ncgc00179456-02

    58. Wln: T5ktj A1 A1 Covxqr&- Al5tj &q &e

    59. Einecs 209-887-0

    60. Mfcd00072137

    61. Bromure De Glycopyrronium [inn-french]

    62. Bromuro De Glicopirronio [inn-spanish]

    63. Chf5259

    64. Glycopyrrolate [usan:usp]

    65. Pt001

    66. Chf-5259

    67. Lonhala Magnair

    68. Pyrrolidinium,1-dimethyl-, Bromide, .alpha.-cyclopentylmandelate

    69. 1,1-dimethyl-3-hydroxypyrrolidinium Bromide .alpha.-cyclopentylmandelate

    70. 1-methyl-3-pyrrolidinyl .alpha.-phenylcyclopentaneglycolate Methobromide

    71. 3-hydroxy-1,1-dimethylpyrrolidinium Bromide-.alpha.-cyclopentylmandelate

    72. Mandelic Acid, Ester With 3-hydroxy-1,1-dimethylpyrrolidinium Bromide

    73. Cuvposa (tn)

    74. Robinul (tn)

    75. Glycopyrrolate (usp)

    76. .beta.-1-methyl-3-pyrrolidyl-.alpha.-cyclopentylmandelate Methobromide

    77. Seebri Breezhaler (tn)

    78. Cas-596-51-0

    79. Glycopyrrone Bromide

    80. Schembl41436

    81. Glycopyrronium Bromide ,(s)

    82. Mls001424112

    83. Mls002222301

    84. 3-hydroxy-1,1-dimethylpyrrolidinium Bromide .alpha.-cyclopentylmandelate

    85. Chembl1201027

    86. Dtxsid6023109

    87. Chebi:90972

    88. Glycopyrrolate, >=98% (hplc)

    89. Glycopyrronium Bromide (jan/inn)

    90. Hms1570e14

    91. Hms2051p12

    92. Hms2094a05

    93. Hms2097e14

    94. Hms2235f12

    95. Hms3259p04

    96. Hms3369f10

    97. Hms3393p12

    98. Hms3714e14

    99. Hms3885p14

    100. Pharmakon1600-01505753

    101. Amy22352

    102. Bcp07110

    103. Bcp33298

    104. Chf-5992

    105. Ex-a4155

    106. Tox21_113144

    107. Tox21_113145

    108. Nsc759238

    109. S4660

    110. Akos015962136

    111. Pyrrolidinium, 1,1-dimethyl-3-hydroxy-, Bromide, Alpha-cyclopentylmandelate

    112. Pyrrolidinium, 3-hydroxy-1,1-dimethyl-, Bromide, Alpha-cyclopentylmandelate

    113. Tox21_113144_1

    114. Ccg-101030

    115. Ccg-213543

    116. Cs-1763

    117. Nc00280

    118. Nc00694

    119. Nsc-759238

    120. Ncgc00179456-04

    121. Ac-23382

    122. Hy-17465

    123. Glycopyrrolate Erythro Isomer (ss-isomer)

    124. Ft-0626787

    125. G0392

    126. D00540

    127. A832400

    128. Sr-01000763650

    129. Sr-01000763650-3

    130. Q27162963

    131. Glycopyrrolate Erythro Isomer (mixture Of Rr-isomer And Ss-isomer)

    132. Glycopyrrolate, United States Pharmacopeia (usp) Reference Standard

    133. Glycopyrronium Bromide, European Pharmacopoeia (ep) Reference Standard

    134. Glycopyrronium Impurity N, European Pharmacopoeia (ep) Reference Standard

    135. 3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidin-1-iumbromide

    136. 3-{[cyclopentyl(hydroxy)phenylacetyl]oxy}-1,1-dimethylpyrrolidin-1-ium Bromide

    137. Glycopyrronium For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    2.3 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 398.3 g/mol
    Molecular Formula C19H28BrNO3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass397.12526 g/mol
    Monoisotopic Mass397.12526 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity424
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 8  
    Drug NameCuvposa
    PubMed HealthGlycopyrrolate
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelCUVPOSA is an anticholinergic drug available as an oral solution containing 1 mg glycopyrrolate per 5 mL. The chemical name for glycopyrrolate is pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl) oxy]-1,1-dimethyl-,bromide. The chemical structure is...
    Active IngredientGlycopyrrolate
    Dosage FormSolution
    RouteOral
    Strength1mg/5ml
    Market StatusPrescription
    CompanyMerz Pharms

    2 of 8  
    Drug NameGlycopyrrolate
    PubMed HealthGlycopyrrolate
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelGlycopyrrolate tablets contain the synthetic anticholinergic glycopyrrolate. Glycopyrrolate is a quaternary ammonium compound with the following chemical name:3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide. Its empirical fo...
    Active IngredientGlycopyrrolate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength1mg; 0.2mg/ml; 1.5mg; 2mg
    Market StatusPrescription
    CompanyStason Pharms; Vintage Pharms; Ranbaxy; Aurolife Pharma; Excellium; Hikma Farmaceutica; Par Pharm; Vintage; Luitpold; Dr Reddys Labs; Nexgen Pharma

    3 of 8  
    Drug NameRobinul
    PubMed HealthGlycopyrrolate
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelROBINUL (glycopyrrolate) Injection is a synthetic anticholinergic agent. Each 1 mL contains:Glycopyrrolate, USP 0.2 mgWater for Injection, USP q.s.Benzyl Alcohol, NF 0.9% (preservative)pH adjusted, when necessary, with hydrochloric acid and/or sodium...
    Active IngredientGlycopyrrolate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength1mg; 0.2mg/ml
    Market StatusPrescription
    CompanyShionogi; Hikma Maple

    4 of 8  
    Drug NameRobinul forte
    PubMed HealthGlycopyrrolate (By mouth)
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelRobinul and Robinul Forte tablets contain the synthetic anticholinergic, glycopyrrolate. Glycopyrrolate is a quaternary ammonium compound with the following chemical name: 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1, 1-dimethylpyrrolidinium bromide...
    Active IngredientGlycopyrrolate
    Dosage FormTablet
    RouteOral
    Strength2mg
    Market StatusPrescription
    CompanyShionogi

    5 of 8  
    Drug NameCuvposa
    PubMed HealthGlycopyrrolate
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelCUVPOSA is an anticholinergic drug available as an oral solution containing 1 mg glycopyrrolate per 5 mL. The chemical name for glycopyrrolate is pyrrolidinium, 3-[(cyclopentylhydroxyphenylacetyl) oxy]-1,1-dimethyl-,bromide. The chemical structure is...
    Active IngredientGlycopyrrolate
    Dosage FormSolution
    RouteOral
    Strength1mg/5ml
    Market StatusPrescription
    CompanyMerz Pharms

    6 of 8  
    Drug NameGlycopyrrolate
    PubMed HealthGlycopyrrolate
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelGlycopyrrolate tablets contain the synthetic anticholinergic glycopyrrolate. Glycopyrrolate is a quaternary ammonium compound with the following chemical name:3-[(cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide. Its empirical fo...
    Active IngredientGlycopyrrolate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength1mg; 0.2mg/ml; 1.5mg; 2mg
    Market StatusPrescription
    CompanyStason Pharms; Vintage Pharms; Ranbaxy; Aurolife Pharma; Excellium; Hikma Farmaceutica; Par Pharm; Vintage; Luitpold; Dr Reddys Labs; Nexgen Pharma

    7 of 8  
    Drug NameRobinul
    PubMed HealthGlycopyrrolate
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelROBINUL (glycopyrrolate) Injection is a synthetic anticholinergic agent. Each 1 mL contains:Glycopyrrolate, USP 0.2 mgWater for Injection, USP q.s.Benzyl Alcohol, NF 0.9% (preservative)pH adjusted, when necessary, with hydrochloric acid and/or sodium...
    Active IngredientGlycopyrrolate
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength1mg; 0.2mg/ml
    Market StatusPrescription
    CompanyShionogi; Hikma Maple

    8 of 8  
    Drug NameRobinul forte
    PubMed HealthGlycopyrrolate (By mouth)
    Drug ClassesCholinergic Antagonist, Gastrointestinal Agent
    Drug LabelRobinul and Robinul Forte tablets contain the synthetic anticholinergic, glycopyrrolate. Glycopyrrolate is a quaternary ammonium compound with the following chemical name: 3-[(cyclopentylhydroxyphenylacetyl)oxy]-1, 1-dimethylpyrrolidinium bromide...
    Active IngredientGlycopyrrolate
    Dosage FormTablet
    RouteOral
    Strength2mg
    Market StatusPrescription
    CompanyShionogi

    4.2 Drug Indication

    Tovanor Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).

    Seebri Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).

    Enurev Breezhaler is indicated as a maintenance bronchodilator treatment to relieve symptoms in adult patients with chronic obstructive pulmonary disease (COPD).

    Symptomatic treatment of severe sialorrhoea (chronic pathological drooling) in children and adolescents aged 3 years and older with chronic neurological disorders.

    Treatment of sialorrhoea

    Chronic obstructive pulmonary disease

    Treatment of sialorrhoea

    Treatment of hyperhidrosis

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Muscarinic Antagonists

    Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

    Adjuvants, Anesthesia

    Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Cholinergic Antagonists [MoA]; Anticholinergic [EPC]
    5.3 ATC Code

    R03BB06

    R03BB06

    R03BB06

    A03AB02

    A03AB02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    A - Alimentary tract and metabolism

    A03 - Drugs for functional gastrointestinal disorders

    A03A - Drugs for functional gastrointestinal disorders

    A03AB - Synthetic anticholinergics, quaternary ammonium compounds

    A03AB02 - Glycopyrronium bromide

    R - Respiratory system

    R03 - Drugs for obstructive airway diseases

    R03B - Other drugs for obstructive airway diseases, inhalants

    R03BB - Anticholinergics

    R03BB06 - Glycopyrronium bromide

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