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

• ChemBase ID: 1369
• Molecular Formular: C27H32N2O6
• Molecular Mass: 480.55278
• Monoisotopic Mass: 480.22603675
• SMILES: O([C@@H]1C2CCN(C1)CC2)C(=O)N1[C@H](c2c(CC1)cccc2)c1ccccc1.OC(=O)CCC(=O)O
• Canonical SMILES: O=C(N1CCc2c([C@@H]1c1ccccc1)cccc2)O[C@H]1CN2CCC1CC2.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-VROPFNGYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: butanedioic acid (3R)-1-azabicyclo[2.2.2]octan-3-yl (1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
• IUPAC Traditional name: @solifenacin; succinic acid
• Brand Name: Vesicare; Vesikur
• Synonyms: solifenacin succinate; Solifenacin

Database IDs

• CAS Number: 242478-37-1
• PubChem SID: 46506006; 160964829
• PubChem CID: 216457

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

DETAILS

DrugBank - DB01591

• Drug Groups: approved
• Description: Solifenacin (rINN), marketed as solifenacin succinate under the trade name Vesicare, is a urinary antispasmodic of the anticholinergic class. It is used in the treatment of overactive bladder with urge incontinence. [Wikipedia]
• Indication: For the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency.
• Pharmacology: Solifenacin is a competitive muscarinic receptor antagonist. Muscarinic receptors play an important role in several major cholinergically mediated functions, including contractions of urinary bladder smooth muscle and stimulation of salivary secretion.
• Toxicity: Overdosage with solifenacin can potentially result in severe anticholinergic effects and should be treated accordingly. The highest solifenacin dose given to human volunteers was a single 100 mg dose. Intolerable anticholinergic side effects (fixed and dilated pupils, blurred vision, failure of heel-to-toe exam, tremors and dry skin) occurred on day 3 in normal volunteers taking 50 mg daily (5 times the maximum recommended therapeutic dose).
• Affected Organisms: Humans and other mammals
• Biotransformation: Solifenacin is extensively metabolized in the liver. The primary pathway for elimination is by way of CYP3A4; however, alternate metabolic pathways exist. The primary metabolic routes of solifenacin are through N-oxidation of the quinuclidin ring and 4R-hydroxylation of tetrahydroisoquinoline ring. One pharmacologically active metabolite (4R-hydroxy solifenacin), occurring at low concentrations and unlikely to contribute significantly to clinical activity, and three pharmacologically inactive metabolites (N-glucuronide and the N-oxide and 4R-hydroxy-N-oxide of solifenacin) have been found in human plasma after oral dosing.
• Absorption: The absolute bioavailability of solifenacin is approximately 90%, and plasma concentrations of solifenacin are proportional to the dose administered.
• Half Life: The elimination half-life of solifenacin following chronic dosing is approximately 45-68 hours.
• Protein Binding: Solifenacin is approximately 98% (in vivo) bound to human plasma proteins, principally to alpha1-acid glycoprotein.
• Elimination: The primary pathway for elimination is by way of CYP3A4; however, alternate metabolic pathways exist.
• Distribution: * 600 L
• External Links: Wikipedia; RxList; Drugs.com