Tiotropium (CED0003758)

Record Information
Version1.0
Creation Date2016-05-25 18:27:26 UTC
Update Date2026-05-14 17:00:10 UTC
Accession NumberCHEM022302
Identification
Common NameTiotropium
ClassSmall Molecule
Description
Tiotropium is an organic compound with the chemical formula C19H22NO4S2 and an average molecular weight of 392.51 g/mol. Tiotropium belongs to the morpholines, a subclass of oxazinanes within the organic compounds. This substance is categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from two recorded sources: electrical and electronic equipment, specifically amplifiers, and healthcare, pharmaceuticals, and veterinary products used as drugs for obstructive airway diseases. Recorded routes of exposure include respiratory and oral pathways. In terms of biological activity, tiotropium acts on five recorded protein targets. It functions as an antagonist of the Muscarinic acetylcholine receptor M1 (CHRM1), Muscarinic acetylcholine receptor M2 (CHRM2), Muscarinic acetylcholine receptor M3 (CHRM3), and Muscarinic acetylcholine receptor M4 (CHRM4), in addition to one other protein.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Tiotropium bromideHMDB
679 BR, BAHMDB
7-((Hydroxybis(2-thienyl)acetyl)oxy)-9,9-dimethyl-3-oxa-9-azoniatricyclo(3.3.1.0(2,4))nonane bromideHMDB
BA679 BRHMDB
BA 679 BRHMDB
BA-679 BRHMDB
SpirivaHMDB
BR, BA 679HMDB
Bromide, tiotropiumHMDB
Chemical FormulaC19H22NO4S2
Average Molecular Mass392.512 g/mol
Monoisotopic Mass392.099 g/mol
CAS Registry Number186691-13-4
IUPAC Name(1R,2S,4R,5S)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-9-ium
Traditional Nametiotropium
SMILESC[N+]1(C)[C@H]2CC(C[C@@H]1[C@@H]1O[C@H]21)OC(=O)C(O)(C1=CC=CS1)C1=CC=CS1
InChI IdentifierInChI=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-
InChI KeyLERNTVKEWCAPOY-KYQOMENCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentMorpholines
Alternative Parents
Substituents
  • Morpholine
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Heteroaromatic compound
  • Tertiary alcohol
  • Thiophene
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic alcohol
  • Organic salt
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP-0.55ALOGPS
logP-1.8ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.35ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.18 m³·mol⁻¹ChemAxon
Polarizability39.69 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-0900000000-ce0b9a60ec794752f2aaNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014i-2490000000-4941aaa9748b0530f3fcNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-0917000000-79ff83b0ed9fdce1df25Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fkc-0934000000-ceda7680df0859576cdeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-db6e02d480976773254fNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
882.0Log mg/kg[500:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
391Drugs for obstructive airway diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Tiotropium Drug Metabolism Action Pathway
Tiotropium Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureMuscarinic receptor 4Q8VH25Cavia porcellusPredicted (SEA)0.467095
Click to view 3D structureMuscarinic acetylcholine receptor M3P08483Rattus norvegicusPredicted (SEA)1.32344
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)14.3243
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)8.48557
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)9.9647
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)6.30579
Click to view 3D structureMuscarinic acetylcholine receptor M3Q8VH26Cavia porcellusPredicted (SEA)1.79053
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)9.03051
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)7.16213
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)6.38364
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)180.454
Click to view 3D structureGlutathione S-transferase theta-1Q01579Rattus norvegicusPredicted (SEA)0.778492
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)168.388
Click to view 3D structureTranslocator proteinP30536HumansPredicted (SEA)26.1573
Click to view 3D structureMuscarinic acetylcholine receptor M1Q8WMX0Bos taurusPredicted (SEA)11.1324
Click to view 3D structureMuscarinic receptor 2Q8VH27Cavia porcellusPredicted (SEA)5.52729
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansPredicted (SEA)480.485
Click to view 3D structureLipoprotein lipaseP11152Mus musculusPredicted (SEA)104.474
Click to view 3D structureMuscarinic acetylcholine receptor M4P08485Rattus norvegicusPredicted (SEA)413.613
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)4023.48
Click to view 3D structureMuscarinic acetylcholine receptor DM1P16395Drosophila melanogasterPredicted (SEA)23.5883
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)6672.22
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)1643.55
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)4872.5
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)4819.72
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0015479
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTiotropium bromide
Chemspider ID2343227
ChEBI IDNot Available
PubChem Compound ID3086655
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References