(3R)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium bromide

• ChemBase ID: 72782
• Molecular Formular: C20H30BrNO3
• Molecular Mass: 412.3611
• Monoisotopic Mass: 411.14090583
• SMILES: [Br-].C12CCC([N+]1(C)C(C)C)C[C@@H](C2)OC(=O)C(c1ccccc1)CO
• Canonical SMILES: OCC(c1ccccc1)C(=O)O[C@@H]1CC2CCC(C1)[N+]2(C)C(C)C.[Br-]
• InChI: InChI=1S/C20H30NO3.BrH/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15;/h4-8,14,16-19,22H,9-13H2,1-3H3;1H/q+1;/p-1/t16?,17?,18-,19?,21?
• InChIKey: LHLMOSXCXGLMMN-VYTJYVGHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium bromide
• IUPAC Traditional name: (3R)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium bromide
• Synonyms: Atrovent; Apovent; Aerovent; Ipratropium bromide

Database IDs

• CAS Number: 22254-24-6
• PubChem SID: 162037703
• PubChem CID: 31098

CALCULATED PROPERTIES

• Acid pKa: 15.14574
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.8177127
• LogD (pH = 7.4): -1.8177124
• Log P: -1.8177127
• Molar Refractivity: 105.8974 cm^3
• Polarizability: 37.49658 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Bromide

DETAILS

Selleck Chemicals - S1683

Research Area: Neurological Disease
Biological Activity:
Ipratropium bromide is a muscarinic antagonist, bronchodilator, N-Isopropyl salt of atropine. In anaesthetised guinea-pigs, bronchoconstriction induced by vagal nerve stimulation was potentiated by low doses of the antimuscarinic bronchodilator drug, ipratropium (0.01-1.0 µg/kg); the maximum effect was obtained with 1.0 µg/kg which doubled the bronchoconstriction. When the dose was increased above 1.0 µg/kg potentiation no longer occurred; instead the vagally induced bronchoconstriction was antagonised. [1]

REFERENCES

• http://www.ncbi.nlm.nih.gov/pubmed/2958300