butanedioic acid (3R)-1-azabicyclo[2.2.2]octan-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

• ChemBase ID: 177826
• Molecular Formular: C27H32N2O6
• Molecular Mass: 480.55278
• Monoisotopic Mass: 480.22603675
• SMILES: C(CC(=O)O)C(=O)O.c12c(CCN([C@@H]1c1ccccc1)C(=O)O[C@H]1CN3CC[C@@H]1CC3)cccc2
• Canonical SMILES: O=C(N1CCc2c([C@H]1c1ccccc1)cccc2)O[C@H]1CN2CC[C@H]1CC2.OC(=O)CCC(=O)O
• InChI: InChI=1S/C23H26N2O2.C4H6O4/c26-23(27-21-16-24-13-10-18(21)11-14-24)25-15-12-17-6-4-5-9-20(17)22(25)19-7-2-1-3-8-19;5-3(6)1-2-4(7)8/h1-9,18,21-22H,10-16H2;1-2H2,(H,5,6)(H,7,8)/t21-,22+;/m0./s1
• InChIKey: RXZMMZZRUPYENV-UMIAIAFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: butanedioic acid (3R)-1-azabicyclo[2.2.2]octan-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
• IUPAC Traditional name: succinic acid (1R,3R,4s)-1-azabicyclo[2.2.2]octan-3-yl (1R)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate
• Synonyms: (1S)-3,4-Dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic Acid (3R)-1-Azabicyclo-[2.2.2]oct-3-yl Ester Hydrochloride; Solifenacin Hydrochloride

Database IDs

• CAS Number: 180468-39-7
• PubChem SID: 164233736
• PubChem CID: 68611540

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.82296765
• LogD (pH = 7.4): 2.4671667
• Log P: 3.9606059
• Molar Refractivity: 106.0582 cm^3
• Polarizability: 41.42036 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Ethanol
• Apperance: White Solid
• Melting Point: 120-122°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S676700

Muscarinic M3 receptor antagoinst. Used in treatment of urinary incontinence.

REFERENCES

• Ikeda K., et al.: Arch. Pharmacol., 366, 97, (2002)
• Chapple, C.R., et al.: Br. J. Urol., 93, 303 (2002)
• Ohtake, A., et al.: Eur. J. Pharmacol., 492, 243 (2002)
• Brunton, S., et al.: Curr. Med. Res. Opin., 21, 71 (2002)
• Habb, F., et al.: Eur. Urol. 47,