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    Ipratropium Bromide

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 22254-24-6, Atrovent, Itrop, Ipratropiumbromid, Bromure d'ipratropium, Bromuro de ipratropio
    Molecular Formula
    C20H30BrNO3
    Molecular Weight
    412.4  g/mol
    InChI Key
    LHLMOSXCXGLMMN-CLTUNHJMSA-M
    FDA UNII
    VJV4X1P2Z1
    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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(1S,5R)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;bromide
    2.1.2 InChI
    InChI=1S/C20H30NO3.BrH/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;1H/q+1;/p-1/t16-,17+,18?,19?,21?;
    2.1.3 InChI Key
    LHLMOSXCXGLMMN-CLTUNHJMSA-M
    2.1.4 Canonical SMILES
    CC(C)[N+]1(C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C.[Br-]
    2.1.5 Isomeric SMILES
    CC(C)[N+]1([C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C.[Br-]
    2.2 Other Identifiers
    2.2.1 UNII
    VJV4X1P2Z1
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (endo,syn)-(+-)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo(3.2.1)octane

    2. Atrovent

    3. Ipratropium

    4. Ipratropium Bromide Anhydrous

    5. Ipratropium Bromide Monohydrate

    6. Ipratropium Bromide, (endo,anti)-isomer

    7. Ipratropium Bromide, (exo,syn)-isomer

    8. Ipratropium Bromide, Endo-isomer

    9. Itrop

    10. N Isopropylatropine

    11. N-isopropylatropine

    12. Sch 1000

    13. Sch 1178

    14. Sch-1000

    15. Sch-1178

    16. Sch1000

    17. Sch1178

    2.3.2 Depositor-Supplied Synonyms

    1. 22254-24-6

    2. Atrovent

    3. Itrop

    4. Ipratropiumbromid

    5. Bromure D'ipratropium

    6. Bromuro De Ipratropio

    7. Sch 1000

    8. 8-isopropylnoratropine Methobromide

    9. Ipratropium Bromide [inn]

    10. Ipratropium Bromide'

    11. Ipratropii Bromidum

    12. N-isopropylnoratropinium Bromomethylate

    13. Ipratropium Bromide Anhydrous

    14. Vjv4x1p2z1

    15. Mls000069557

    16. 60251-88-9

    17. Ipratropiumbromide

    18. Smr000058764

    19. (1r,5s)-3-((3-hydroxy-2-phenylpropanoyl)oxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium Bromide

    20. 24358-20-1

    21. Ipratropium Bromide Monohydrate

    22. 8-azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, Bromide (1:1), (3-exo,8-syn)-

    23. Rel-(1r,3r,5s,8r)-3-((3-hydroxy-2-phenylpropanoyl)oxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium Bromide

    24. Atem

    25. 66985-17-9

    26. Ipratropiumbromid [german]

    27. Unii-vjv4x1p2z1

    28. Ipratropii Bromidum [inn-latin]

    29. Prestwick_279

    30. Bromure D'ipratropium [inn-french]

    31. Einecs 244-873-8

    32. Einecs 261-098-0

    33. Einecs 262-128-5

    34. Bromuro De Ipratropio [inn-spanish]

    35. Opera_id_1621

    36. Schembl3852

    37. Schembl3854

    38. Schembl107906

    39. (1s,3s,5r)-3-tropyloxy-8-isopropyltropanium Bromide

    40. Ipratropium Bromide (anhydrous)

    41. Chembl1464005

    42. Ipratropium Bromide [mi]

    43. Regid_for_cid_657308

    44. Schembl16762661

    45. Chebi:46659

    46. Dtxsid10860753

    47. Dtxsid60858923

    48. Hms2234j05

    49. Einecs 246-197-9

    50. Bdbm50021892

    51. Ipratropium Bromide [who-dd]

    52. Mfcd00069291

    53. Akos015895324

    54. Akos030485952

    55. (8r)-3-alpha-hydroxy-8-isopropyl-1-alpha-h,5-alpha-h-tropiumbromide-(+-)-tropate

    56. 3-alpha-hydroxy-8-isopropyl-1-alpha-h,5-alpha-h-tropanium Bromide (+-)-tropate

    57. (endo,anti)-(1)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-isopropyl-8-methyl-8-azoniabicyclo(3.2.1)octane Bromide

    58. (exo,syn)-(1)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-isopropyl-8-methyl-8-azoniabicyclo(3.2.1)octane Bromide

    59. Bi164579

    60. N-isopropylnortropine Tropate Methobromide

    61. C74140

    62. T72808

    63. Q424294

    64. 3alpha-hydroxy-8-isopropyl-1alphah,5alphah-tropanium Bromide (+-)-tropate

    65. 1-alpha-h,5-alpha-h-tropanium, 3-alpha-hydroxy-8-isopropyl-, Bromide, (+-)-tropate

    66. (1r,3r,5s)-3-(3-hydroxy-2-phenylpropanoyloxy)-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octane Bromide

    67. (3-endo,8-syn)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azoniabicyclo[3.2.1]octane Bromide

    68. (endo,syn)-(+-)-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane Bromide

    69. 8-azoniabicyclo(3.2.1)octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, Bromide, Endo-

    70. Endo-3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-isopropyl-8-methyl-8-azoniabicyclo(3.2.1)octane Bromide

    71. Rel-(1r,3r,5s,8s)-3-((3-hydroxy-2-phenylpropanoyl)oxy)-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium Bromide

    2.4 Create Date
    2005-06-29
    3 Chemical and Physical Properties
    Molecular Weight 412.4 g/mol
    Molecular Formula C20H30BrNO3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count6
    Exact Mass411.14091 g/mol
    Monoisotopic Mass411.14091 g/mol
    Topological Polar Surface Area46.5 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity430
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameAtrovent
    PubMed HealthIpratropium (Into the nose)
    Drug ClassesNasal Agent
    Drug LabelThe active ingredient in ATROVENT Nasal Spray is ipratropium bromide (as the monohydrate). It is an anticholinergic agent chemically described as 8-azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide m...
    Active IngredientIpratropium bromide
    Dosage FormSpray, metered
    RouteNasal
    Strength0.042mg/spray; 0.021mg/spray
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    2 of 4  
    Drug NameIpratropium bromide
    PubMed HealthIpratropium
    Drug ClassesBronchodilator, Nasal Agent
    Drug LabelThe active ingredient in Ipratropium Bromide Nasal Solution 0.03% (Nasal Spray) is ipratropium bromide monohydrate. It is an anticholinergic agent chemically described as 8-azoniabicyclo [3.2.1] octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-...
    Active IngredientIpratropium bromide
    Dosage FormSpray, metered; Solution
    RouteNasal; Inhalation
    Strength0.042mg/spray; 0.02%; 0.021mg/spray
    Market StatusPrescription
    CompanyRitedose; Nephron; Mylan Speclt; Roxane; Watson Labs; Bausch And Lomb; Landela Pharm

    3 of 4  
    Drug NameAtrovent
    PubMed HealthIpratropium (Into the nose)
    Drug ClassesNasal Agent
    Drug LabelThe active ingredient in ATROVENT Nasal Spray is ipratropium bromide (as the monohydrate). It is an anticholinergic agent chemically described as 8-azoniabicyclo[3.2.1]octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-(1-methylethyl)-, bromide m...
    Active IngredientIpratropium bromide
    Dosage FormSpray, metered
    RouteNasal
    Strength0.042mg/spray; 0.021mg/spray
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    4 of 4  
    Drug NameIpratropium bromide
    PubMed HealthIpratropium
    Drug ClassesBronchodilator, Nasal Agent
    Drug LabelThe active ingredient in Ipratropium Bromide Nasal Solution 0.03% (Nasal Spray) is ipratropium bromide monohydrate. It is an anticholinergic agent chemically described as 8-azoniabicyclo [3.2.1] octane, 3-(3-hydroxy-1-oxo-2-phenylpropoxy)-8-methyl-8-...
    Active IngredientIpratropium bromide
    Dosage FormSpray, metered; Solution
    RouteNasal; Inhalation
    Strength0.042mg/spray; 0.02%; 0.021mg/spray
    Market StatusPrescription
    CompanyRitedose; Nephron; Mylan Speclt; Roxane; Watson Labs; Bausch And Lomb; Landela Pharm

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Bronchodilator Agents

    Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

    Cholinergic Antagonists

    Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists. (See all compounds classified as Cholinergic Antagonists.)

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

    R03BB01

    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

    R - Respiratory system

    R01 - Nasal preparations

    R01A - Decongestants and other nasal preparations for topical use

    R01AX - Other nasal preparations

    R01AX03 - Ipratropium bromide

    R - Respiratory system

    R03 - Drugs for obstructive airway diseases

    R03B - Other drugs for obstructive airway diseases, inhalants

    R03BB - Anticholinergics

    R03BB01 - Ipratropium bromide