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    Chemistry

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    Also known as: 136310-93-5, Spiriva, Ba 679 br, Tiotropium (bromide), Spiriva handihaler, Ba 679br
    Molecular Formula
    C19H22BrNO4S2
    Molecular Weight
    472.4  g/mol
    InChI Key
    DQHNAVOVODVIMG-RGECMCKFSA-M
    FDA UNII
    XX112XZP0J
    Tiotropium Bromide
    A scopolamine derivative and CHOLINERGIC ANTAGONIST that functions as a BRONCHODILATOR AGENT. It is used in the treatment of CHRONIC OBSTRUCTIVE PULMONARY DISEASE.
    1 2D Structure

    Tiotropium Bromide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(1R,2R,4S,5S)-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;bromide
    2.1.2 InChI
    InChI=1S/C19H22NO4S2.BrH/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15;/h3-8,11-13,16-17,22H,9-10H2,1-2H3;1H/q+1;/p-1/t11?,12-,13+,16-,17+;
    2.1.3 InChI Key
    DQHNAVOVODVIMG-RGECMCKFSA-M
    2.1.4 Canonical SMILES
    C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.[Br-]
    2.1.5 Isomeric SMILES
    C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)C(C4=CC=CS4)(C5=CC=CS5)O)C.[Br-]
    2.2 Other Identifiers
    2.2.1 UNII
    XX112XZP0J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 679 Br, Ba

    2. 7-((hydroxybis(2-thienyl)acetyl)oxy)-9,9-dimethyl-3-oxa-9-azoniatricyclo(3.3.1.0(2,4))nonane Bromide

    3. Ba 679 Br

    4. Ba-679 Br

    5. Ba679 Br

    6. Br, Ba 679

    7. Bromide, Tiotropium

    8. Spiriva

    9. Tiotropium

    2.3.2 Depositor-Supplied Synonyms

    1. 136310-93-5

    2. Spiriva

    3. Ba 679 Br

    4. Tiotropium (bromide)

    5. Spiriva Handihaler

    6. Ba 679br

    7. Ba-679 Br

    8. Spiriva Respimat

    9. (1r,2r,4s,5s,7s)-7-(2-hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium Bromide

    10. Xx112xzp0j

    11. Chembl4638964

    12. 7-((hydroxybis(2-thienyl)acetyl)oxy)-9,9-dimethyl-3-oxa-9-azoniatricyclo(3.3.1.0(2,4))nonane Bromide

    13. Ba-679-br

    14. (1r,2r,4s,5s,7r)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium Bromide

    15. (1r,2r,4s,5s,7s)-7-(2-hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0

    16. Tiopropium

    17. Tiotropium Bromide Anhydrous

    18. Ba-679br

    19. (1a,2b,4b,5a,7b)-7-[(hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane Bromide

    20. Ncgc00167971-01

    21. Tiotropium Bromide [inn]

    22. Unii-xx112xzp0j

    23. Tiotropium Bromide [usan:inn:ban]

    24. Tiotropium Bromide- Bio-x

    25. Schembl8625

    26. Dsstox_cid_24214

    27. Dsstox_rid_80122

    28. Dsstox_gsid_44214

    29. Schembl440873

    30. Schembl7607795

    31. Tiotropium Bromide [mi]

    32. Chembl3189058

    33. Chembl4440620

    34. Dtxsid2044214

    35. Chebi:90959

    36. Tiotropium Bromide [usan]

    37. Hms2090h20

    38. Act04740

    39. Act04741

    40. Amy23428

    41. Bcp02925

    42. Tiotropium Bromide [who-dd]

    43. Tox21_112598

    44. Bdbm50538220

    45. Mfcd00867027

    46. Akos015920264

    47. Akos025400979

    48. Ac-1300

    49. Cs-0903

    50. Ks-1402

    51. Tiotropium Bromide [orange Book]

    52. Tiotropium Bromide(spiriva, Ba 679br)

    53. As-75172

    54. Bt164474

    55. Hy-17360

    56. Bcp0726000293

    57. Cas-136310-93-5

    58. T3032

    59. A846824

    60. Q27162952

    61. (1?,2?,4?,5?,7?)-7-[(2-hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane Bromide

    62. (1alpha,2beta,4beta,5alpha,7beta)-7-[(hydroxydi-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.0(2,4)]nonane Bromide

    63. (1r,2r,4s,5s)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0(2),?]nonan-9-ium Bromide

    64. (1r,2r,4s,5s,7r)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0?,?]nonan-9-ium Bromide

    65. (1r,2r,4s,5s,7s)-7-[2-hydroxy-2,2-di(2-thienyl)acetoxy]-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium Bromide

    66. [(1r,2r,4s,5s)-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;bromide

    67. [(1r,2r,4s,5s)-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonan-7-yl]2-hydroxy-2,2-dithiophen-2-yl-acetate Bromide

    68. 1.alpha., 2.beta., 4.beta, 5.alpha, 7.beta-7-((hydroxydi-2-thienylacetyl)oxy)-9,9-dimethyl-3-oxa-9-azoniatricyclo(3.3.1.0 Sup(2,4))nonane Bromide

    69. 3-oxa-9-azoniatricyclo(3,3.1.0(2,4))nonane, 7-((hydroxydi-2-thienylacetyl)oxy)-9,9-dimethyl-, Bromide, (1alpha,2beta,4beta,5alpha,7beta)-

    70. 3-oxa-9-azoniatricyclo(3.3.1.02,4)nonane, 7-((hydroxydi-2-thienacetyl)oxy)-9,9-dimethyl-, Bromide, (1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)-

    71. 3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane, 7-[(2-hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-dimethyl-, Bromide (1:1), (1alpha,2beta,4beta,5alpha,7beta)-

    72. 6.beta.,7.beta.-epoxy-3.beta.-hydroxy-8-methyl-1.alpha.h,5.alpha.h-tropanium Bromide, Di-2-thienylglycolate

    73. Rel-(1r,2r,4s,5s,7s)-7-(2-hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium Bromide

    74. Rel-(1r,2r,4s,5s,7s)-7-(2-hydroxy-2,2-di(thiophen-2-yl)acetoxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-iumbromide

    2.3.3 Other Synonyms

    1. Tiotropiumbromide

    2. Gsp 304

    3. Tiotropium Cation

    4. Respimat

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 472.4 g/mol
    Molecular Formula C19H22BrNO4S2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count5
    Exact Mass471.01736 g/mol
    Monoisotopic Mass471.01736 g/mol
    Topological Polar Surface Area116 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity564
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    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 NameSpiriva
    PubMed Healthtiotropium
    Drug ClassesBronchodilator
    Drug LabelSPIRIVA HandiHaler consists of a capsule dosage form containing a dry powder formulation of tiotropium intended for oral inhalation only with the HandiHaler device.Each light green, hard gelatin SPIRIVA capsule contains 18 mcg tiotropium (equivalent...
    Active IngredientTiotropium bromide
    Dosage FormPowder
    RouteInhalation
    Strengtheq 0.018mg base/inh
    Market StatusPrescription
    CompanyBoehringer Ingelheim
    Patent8022082; 6908928; RE38912; 7694676; RE39820; 7309707; 7642268; 7070800; 6777423

    2 of 4  
    Drug NameSpiriva respimat
    PubMed Healthtiotropium
    Drug LabelThe active component of SPIRIVA RESPIMAT is tiotropium. The drug substance, tiotropium bromide monohydrate, is an anticholinergic with specificity for muscarinic receptors. It is chemically described as (1, 2, 4, 5, 7)-7-[(Hydroxydi-2-thien...
    Active IngredientTiotropium bromide
    Dosage FormSpray, metered
    RouteInhalation
    Strengtheq 0.0025mg base/inh
    Market StatusPrescription
    CompanyBoehringer Ingelheim
    Patent7284474; 7802568; 6977042; 5964416; 7988001; 6176242; 6453795; RE39820; 7246615; 6988496; 7896264; 7837235; 6726124; 6846413; 6149054; 7396341; 7104470

    3 of 4  
    Drug NameSpiriva
    PubMed Healthtiotropium
    Drug ClassesBronchodilator
    Drug LabelSPIRIVA HandiHaler consists of a capsule dosage form containing a dry powder formulation of tiotropium intended for oral inhalation only with the HandiHaler device.Each light green, hard gelatin SPIRIVA capsule contains 18 mcg tiotropium (equivalent...
    Active IngredientTiotropium bromide
    Dosage FormPowder
    RouteInhalation
    Strengtheq 0.018mg base/inh
    Market StatusPrescription
    CompanyBoehringer Ingelheim
    Patent8022082; 6908928; RE38912; 7694676; RE39820; 7309707; 7642268; 7070800; 6777423

    4 of 4  
    Drug NameSpiriva respimat
    PubMed Healthtiotropium
    Drug LabelThe active component of SPIRIVA RESPIMAT is tiotropium. The drug substance, tiotropium bromide monohydrate, is an anticholinergic with specificity for muscarinic receptors. It is chemically described as (1, 2, 4, 5, 7)-7-[(Hydroxydi-2-thien...
    Active IngredientTiotropium bromide
    Dosage FormSpray, metered
    RouteInhalation
    Strengtheq 0.0025mg base/inh
    Market StatusPrescription
    CompanyBoehringer Ingelheim
    Patent7284474; 7802568; 6977042; 5964416; 7988001; 6176242; 6453795; RE39820; 7246615; 6988496; 7896264; 7837235; 6726124; 6846413; 6149054; 7396341; 7104470

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    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.)

    Parasympatholytics

    Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

    Bronchodilator Agents

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

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

    R03BB04

    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

    R03 - Drugs for obstructive airway diseases

    R03B - Other drugs for obstructive airway diseases, inhalants

    R03BB - Anticholinergics

    R03BB04 - Tiotropium bromide

    API Reference Price

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    28-Jan-2021
    25-Sep-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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