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 bromide

• ChemBase ID: 178666
• Molecular Formular: C19H22BrNO4S2
• Molecular Mass: 472.41628
• Monoisotopic Mass: 471.01736219
• SMILES: C12C3C(C(CC(C1)OC(=O)C(c1cccs1)(c1sccc1)O)[N+]2(C)C)O3.[Br-]
• Canonical SMILES: O=C(C(c1cccs1)(c1cccs1)O)OC1CC2C3C(C(C1)[N+]2(C)C)O3.[Br-]
• 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
• InChIKey: DQHNAVOVODVIMG-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 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
• IUPAC Traditional name: 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
• Synonyms: (1α,2β,4β,5α,7β)-7-[(2-Hydroxy-2,2-di-2-thienylacetyl)oxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane Bromide; Tiotropium Bromide

Database IDs

• CAS Number: 136310-93-5
• PubChem SID: 164234576
• PubChem CID: 60830

CALCULATED PROPERTIES

• Acid pKa: 10.351076
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.7571676
• LogD (pH = 7.4): -1.7481594
• Log P: -1.7572837
• Molar Refractivity: 109.182 cm^3
• Polarizability: 38.91962 Å^3
• Polar Surface Area: 59.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 218-220°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T444850

Muscarinic receptor antagonist. Bronchodilator.

REFERENCES

• Haddad, E.-B., et al.: Mol. Pharmacol., 45, 899 (1994)
• Donohue, J. F., et al.: Chest, 122, 47 (1994)
• Profita, M., et al.: Allergy, 60, 1361 (1994)
• Dusser, D., et al.: Eur. Respir. J., 27, 547 (1994)