2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide hydrobromide

• ChemBase ID: 165412
• Molecular Formular: C28H31BrN2O2
• Molecular Mass: 507.46194
• Monoisotopic Mass: 506.15689024
• SMILES: C(Cc1cc2c(cc1)OCC2)N1C[C@@H](CC1)C(c1ccccc1)(c1ccccc1)C(=O)N.Br
• Canonical SMILES: NC(=O)C(c1ccccc1)(c1ccccc1)[C@@H]1CCN(C1)CCc1ccc2c(c1)CCO2.Br
• InChI: InChI=1S/C28H30N2O2.BrH/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26;/h1-12,19,25H,13-18,20H2,(H2,29,31);1H/t25-;/m1./s1
• InChIKey: UQAVIASOPREUIT-VQIWEWKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide hydrobromide
• IUPAC Traditional name: darifenacin hydrobromide; 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide hydrobromide
• Synonyms: Enablex; Emselex; Darifenacin Hydrobromide; (3S)-1-[2-(2,3-Dihydro-5-benzofuranyl)ethyl]-α-α-diphenyl-3-pyrrolidineacetamide Hydrobromide; Darifenacin hydrobromide; Darifenacin HBr

Database IDs

• CAS Number: 133099-07-7
• PubChem SID: 162259545
• PubChem CID: 444030

CALCULATED PROPERTIES

• Acid pKa: 16.212147
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.0715904
• LogD (pH = 7.4): 1.896206
• Log P: 4.540284
• Molar Refractivity: 128.3747 cm^3
• Polarizability: 49.758102 Å^3
• Polar Surface Area: 55.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 228-230°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: AChR
• Mechanism of Action: Works by blocking the M3 muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions

Product Information

• Salt Data: HBr
• Application(s): Used to treat urinary incontinence

DETAILS

Toronto Research Chemicals - D193400

Used as a medication to treat urinary incontinence. It works by blocking the M3 muscarinic acetylcholine receptor.

REFERENCES

• Beaumont, K.C., et al.: Xenobiotica, 28, 63 (1998)
• Chapple, C.R., et al.: Expert Opin. Invest. Drugs, 13, 1493 (1998)
• Haab, F., et al.: Eur. Urol., 45, 420 (1998)
• Liver Physiol. 2010 Jul;299(1):G215-9. Epub 2010 Apr 15.
• 3. Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16.
• 1. Bharucha AE, Ravi K, Zinsmeister AR: Comparison of selective M3 and nonselective muscarinic receptor antagonists on gastrointestinal transit and bowel habits in humans. Am J Physiol Gastrointest
• 2. Bozkurt TE, Sahin-Erdemli I: M(1) and M(3) muscarinic receptors are involved in the release of urinary bladder-derived relaxant factor. Pharmacol Res. 2009 May;59(5):300-5. Epub 2009 Feb 5.