0HK

(1R,2R,4S,5S,7S)-7-{[hydroxy(dithiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.0~2,4~]nonane

Created: 2012-01-18
Last modified:  2021-03-01

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Chemical Details

Formal Charge1
Atom Count48
Chiral Atom Count4
Bond Count52
Aromatic Bond Count10
2D diagram of 0HK

Chemical Component Summary

Name(1R,2R,4S,5S,7S)-7-{[hydroxy(dithiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.0~2,4~]nonane
SynonymsTiotropium
Systematic Name (OpenEye OEToolkits)n/a
FormulaC19 H22 N O4 S2
Molecular Weight392.512
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(OC3CC1[N+](C)(C)C(C2OC12)C3)C(O)(c4sccc4)c5sccc5
SMILESCACTVS3.370C[N+]1(C)[CH]2CC(C[CH]1[CH]3O[CH]23)OC(=O)C(O)(c4sccc4)c5sccc5
SMILESOpenEye OEToolkits1.7.6C[N+]1(C2CC(CC1C3C2O3)OC(=O)C(c4cccs4)(c5cccs5)O)C
Canonical SMILESCACTVS3.370 C[N+]1(C)[C@@H]2CC(C[C@H]1[C@@H]3O[C@H]23)OC(=O)C(O)(c4sccc4)c5sccc5
Canonical SMILESOpenEye OEToolkits1.7.6 C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)C(c4cccs4)(c5cccs5)O)C
InChIInChI1.03 InChI=1S/C19H22NO4S2/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/q+1/t11-,12-,13+,16-,17+
InChIKeyInChI1.03 LERNTVKEWCAPOY-DZZGSBJMSA-N

Drug Info: DrugBank

DrugBank IDDB01409 
NameTiotropium
Groups approved
DescriptionTiotropium is a long-acting, antimuscarinic bronchodilator used in the management of chronic obstructive pulmonary disease (COPD) and asthma.[A180163,L7084,L7087,L7090,L7093] Tiotropium acts mainly on M3 muscarinic receptors located in the airways to produce smooth muscle relaxation and bronchodilation.[A180163,L7084,L7087,L7090,L7093] Tiotropium is more specific for the subset of muscarinic receptors commonly found in the lungs than [ipratropium].[A180163] Tiotropium was granted FDA approval on 30 January 2004.[L7084]
Synonyms
  • Tiotropium
  • Tiotropium bromide monohydrate
  • Tiotropium bromide
Brand Names
  • Spiriva HandiHaler
  • Lupin-tiotropium
  • Inspiolto Respimat
  • Spiriva
  • Stiolto Respimat
IndicationTiotropium powder for inhalation is indicated for the maintenance of bronchospasm in COPD and to prevent exacerbations of COPD.[L7084] A combination tiotropium and [olodaterol] metered inhalation spray is indicated for maintenance of COPD.[L7087] A tiotropium inhalation spray is indicated for the maintenance of bronchospasm in COPD, to prevent exacerbations of COPD, and to treat asthma in patients 12 or more years old.[L7090] A tiotropium metered inhalation spray is indicated for the maintenance of bronchospasm in COPD, to prevent exacerbations of COPD, and to treat asthma in patients 6 or more years old.[L7093]
Categories
  • Adrenergics, Inhalants
  • Agents producing tachycardia
  • Agents to Treat Airway Disease
  • Alkaloids
  • Anti-Asthmatic Agents
ATC-Code
  • R03AL06
  • R03BB04
  • R03BB54
  • R03AL10
CAS number186691-13-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Muscarinic acetylcholine receptor M3MTLHNNSTTSPLFPNISSSWIHSPSDAGLPPGTVTHFGSYNVSRAAGNFS...unknownantagonist
Muscarinic acetylcholine receptor M1MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...unknownantagonist
Muscarinic acetylcholine receptor M2MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...unknownantagonist
Muscarinic acetylcholine receptor M4MANFTPVNGSSGNQSVRLVTSSSHNRYETVEMVFIATVTGSLSLVTVVGN...unknown
Muscarinic acetylcholine receptor M5MEGDSYHNATTVNGTPVNHQPLERHRLWEVITIAAVTAVVSLITIVGNVL...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
CCDC/CSD GUYGOX03