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133099-04-4 molecular structure
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2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide

ChemBase ID: 379
Molecular Formular: C28H30N2O2
Molecular Mass: 426.55
Monoisotopic Mass: 426.23072821
SMILES and InChIs

SMILES:
O=C(N)C([C@@H]1CCN(C1)CCc1cc2c(OCC2)cc1)(c1ccccc1)c1ccccc1
Canonical SMILES:
NC(=O)C(c1ccccc1)(c1ccccc1)[C@@H]1CCN(C1)CCc1ccc2c(c1)CCO2
InChI:
InChI=1S/C28H30N2O2/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)/t25-/m1/s1
InChIKey:
HXGBXQDTNZMWGS-RUZDIDTESA-N

Cite this record

CBID:379 http://www.chembase.cn/molecule-379.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide
IUPAC Traditional name
enablex
Brand Name
Enablex
Emselex
Synonyms
darifenacin
Darifenacin
CAS Number
133099-04-4
PubChem SID
160963842
46508104
PubChem CID
444031

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.212147  H Acceptors
H Donor LogD (pH = 5.5) 1.0715904 
LogD (pH = 7.4) 1.896206  Log P 4.540284 
Molar Refractivity 128.3747 cm3 Polarizability 49.758102 Å3
Polar Surface Area 55.56 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.35  LOG S -6.16 
Solubility (Water) 2.98e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
4.5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00496 external link
Item Information
Drug Groups approved; investigational
Description Darifenacin (Enablex?, Novartis) is a medication used to treat urinary incontinence.

Darifenacin works by blocking the M3 muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions. It thereby decreases the urgency to urinate. It should not be used in people with urinary retention.

It is not known whether this selectivity for the M3 receptor translates into any clinical advantage when treating symptoms of overactive bladder syndrome.
Indication For the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency and frequency.
Pharmacology Darifenacin is a competitive muscarinic receptor antagonist. In vitro studies using human recombinant muscarinic receptor subtypes show that darifenacin has greater affinity for the M3 receptor than for the other known muscarinic receptors (9 and 12-fold greater affinity for M3 compared to M1 and M5, respectively, and 59-fold greater affinity for M3 compared to both M2 and M4). Muscarinic receptors play an important role in several major cholinergically mediated functions, including contractions of the urinary bladder smooth muscle and stimulation of salivary secretion. Adverse drug effects such as dry mouth, constipation and abnormal vision may be mediated through effects on M3 receptors in these organs.
Toxicity Overdosage can potentially result in severe central anticholinergic effects.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Primarily mediated by the cytochrome P450 enzymes CYP2D6 and CYP3A4.
Absorption The mean oral bioavailability at steady state is estimated to be 15% and 19% for 7.5 mg and 15 mg tablets, respectively.
Half Life The elimination half-life of darifenacin following chronic dosing is approximately 13-19 hours.
Protein Binding Darifenacin is approximately 98% bound to plasma proteins (primarily to alpha-1-acid-glycoprotein).
Distribution * 163 L
Clearance * 40 L/h [extensive metabolizers]
* 32 L/h [poor metabolizers]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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PATENTS

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