Darifenacin HBr

Names

[ Name ]:
Darifenacin HBr

[Synonym ]:
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofur-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamidhydrobromid
2-{(3S)-1-[2-(2,3-dihydro-1-benzofur-5-yl)éthyl]pyrrolidin-3-yl}-2,2-diphénylacétamide bromhydrate
2-{(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide hydrobromide
3-Pyrrolidineacetamide, 1-[2-(2,3-dihydro-5-benzofuranyl)ethyl]-α,α-diphenyl-, (3S)-, hydrobromide (1:1)
UNII-CR02EYQ8GV
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide hydrobromide (1:1)
Darifenacin hydrobromide
2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide,hydrobromide
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide hydrobromide (1:1)
Darifenacin HBr
Emselex
2-{(3S)-1-[2-(2,3-Dihydro-1-benzofur-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamidhydrobromid(1:1)
3-pyrrolidineacetamide, 1-[2-(2,3-dihydro-5-benzofuranyl)ethyl]-α,α-diphenyl-, (3S)-, monohydrobromide
Enablex
Darifenacin (hydrobromide)

Biological Activity

[Description]:

Darifenacin HBr(UK88525) is a selective M3 muscarinic receptor antagonist with pKi of 8.9.IC50 value: 8.9 (pKi) [1]Target: M3 receptorin vitro: Darifenacin exerts non-parallel rightward displacement of the agonist curve and also significant depression of the maximum response (+)-cis-Dioxolane produced concentration-dependent contraction of the isolated bladder of rat [1]. Darifenacin produces a concentration dependent increase in R123 (P-gp probe) accumulation in MDCK cells. Darifenacin stimulates ATPase activity in P-gp membrane in a clear concentration dependent response manner with an estimated ED50 value of 1.6?μM. Darifenacin (100 nM) shows a significantly greater permeability for darifenacin in the basolateral to apical direction resulting in an efflux ratio in BBMEC monolayers of approximately 2.6 [2].in vivo: Darifenacin produces dose-dependent inhibition of amplitude of volume-induced bladder contractions(VIBCAMP), producing 35% inhibition at dose of 283.3 nmol/kg and maximal inhibition of approximately 50–55% [1]. Darifenacin (0.1 mg/kg i.v.) reduces bladder afferent activity in both Aδ and C fibers in female Sprague-Dawley rats, the decrease in afferent spikes in C fibers may be more pronounced than that in Aδ fibers [3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> mAChR

Signaling Pathways >> Neuronal Signaling >> mAChR

Research Areas >> Neurological Disease

[References]

[1]. Hegde SS, et al. Functional role of M2 and M3 muscarinic receptors in the urinary bladder of rats in vitro and in vivo. Br J Pharmacol, 1997, 120(8), 1409-1418.

[2]. Miller DW, et al. Evaluation of drug efflux transporter liabilities of darifenacin in cell culture models of the blood-brain and blood-ocular barriers. Neurourol Urodyn, 2011, 30(8), 1633-1638.

[3]. Iijima K, et al. Effects of the M3 receptor selective muscarinic antagonist darifenacin on bladder afferent activity of the rat pelvic nerve. Eur Urol, 2007, 52(3), 842-847.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
614.3ºC at 760 mmHg

[ Melting Point ]:
228-230ºC

[ Molecular Formula ]:
C₂₈H₃₁BrN₂O₂

[ Molecular Weight ]:
507.46

[ Flash Point ]:
325.3ºC

[ PSA ]:
41.57000

[ LogP ]:
5.94630

[ Vapour Pressure ]:
1.11E-16mmHg at 25°C

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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