(1R,3R,5S)-3-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium bromide

• ChemBase ID: 179698
• Molecular Formular: C20H30BrNO3
• Molecular Mass: 412.3611
• Monoisotopic Mass: 411.14090583
• SMILES: [N+]1([C@@H]2C[C@H](C[C@H]1CC2)OC(=O)[C@H](c1ccccc1)CO)(C(C)C)C.[Br-]
• Canonical SMILES: OC[C@@H](c1ccccc1)C(=O)O[C@@H]1C[C@@H]2CC[C@H](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-WDTICOSOSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S)-3-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium bromide
• IUPAC Traditional name: (1R,3R,5S)-3-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium bromide
• Synonyms: Atrovent; Atem; Berodual; Itrop; Narilet; Normosecretol; Respontin; Rinatec; Tropiovent; Ipratropium Bromide

Database IDs

• CAS Number: 22254-24-6
• PubChem SID: 164235608
• PubChem CID: 51052074

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

Pharmacology Properties

• Mechanism of Action: Blocker of muscarinic receptors in the lung, inhibiting bronchoconstriction and mucus secretion; Bronchodilator

Product Information

• Salt Data: Br-
• Application(s): Antiarrhythmic; Antimuscarinic agent; Antispasmodic agent; Bronchodilator

REFERENCES

• South African Pat., 1968, Boehringer Ingelheim, 6 707 766; CA, 70, 97033u, (synth, pharmacol)
• Pook, K.H. et al., Annalen, 1975, 1499, (nmr)
• Deckers, W., Postgrad. Med. J., Suppl., No. 7, 1975, 51, 76, (synth, pharmacol)
• Bauer, R. et al., Arzneim.-Forsch., 1976, 26, 974, (pharmacol)
• Sarajana, L. et al., Arzneim.-Forsch., 1976, 26, 985, (tox)
• Bauer, R. et al., Pharmacol. Biochem. Prop. Drug Subst., 1979, 2, 489, (rev)
• Massey, K.L. et al., Drug Intell. Clin. Pharm., 1985, 19, 5, (rev)
• Gross, N.J. et al., N. Engl. J. Med., 1988, 319, 486, (rev, pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8062, (synonyms)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 754
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, IGG000