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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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30-Jan-2021
31-Aug-2024
KGS
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