385367-47-5

Basic information

• Product Name: Tarafenacin
• Synonyms: Tarafenacin;SVT-40776 (Tarafenacin);N-(3-Fluorophenyl)-N-[(3,4,5-trifluorophenyl)methyl]carbamic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester;Tarafenacin, >=98%;SVT407776
• CAS NO: 385367-47-5
• Molecular Formula: C21H20F4N2O2
• Molecular Weight: 408.3893128
• Mol File: 385367-47-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 483.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.38
• Solubility: Soluble in DMSO
• PKA: 8.80±0.33(Predicted)
• CAS DataBase Reference: Tarafenacin(CAS DataBase Reference)
• NIST Chemistry Reference: Tarafenacin(385367-47-5)
• EPA Substance Registry System: Tarafenacin(385367-47-5)

Safety Data

• Hazardous Substances Data: 385367-47-5(Hazardous Substances Data)

Usage

Biological Activity

tarafenacin is a selective antagonist of m3 muscarinic receptor with ki value of 0.19nm [1].tarafenacin is a novel quinuclidine derivative and is developed as an antimuscarinic drug for treatment of overactive bladder. it shows a 203-fold selectivity with m3 receptor over m2 receptor. tarafenacin reduces the maximum carbachol response at concentrations of 10nm and 100nm in mouse isolated bladder. in mouse atrial preparations, tarafenacin slightly attenuates the effects on heart rate caused by carbachol. tarafenacin shows a 199-fold urinary affinity against cardiac affinity. it is a highly potent antagonist in the bladder and lacks any relevant effect in atria at the same range of concentrations. in the guinea pig model, tarafenacin significantly changes the bladder contraction amplitude. it inhibits 25% of spontaneous bladder contractions at dose of 17.1nmol/kg [1].

references

[1] salcedo c, davalillo s, cabellos j, et al. in vivo and in vitro pharmacological characterization of svt-40776, a novel m3 muscarinic receptor antagonist, for the treatment of overactive bladder. british journal of pharmacology, 2009, 156(5): 807-817.

Upstream product

• 552860-82-9 (3R)-(3-fluorophenyl)-(3,4,5-trifluorobenzyl) carbamic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester hydrochloride 
• 132123-54-7 3,4,5-trifluorobenzaldehyde 
• 372-19-0 meta-fluoroaniline 
• 637744-48-0 (3-fluorophenyl)(3,4,5-trifluorobenzyl)carbamoyl chloride 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 1202493-05-7 C₁₃H₇F₄N 
• 637744-49-1 (3-Fluorophenyl)-(3,4,5-trifluorobenzyl)amine 
• 552831-23-9 (R)-imidazole-1-carboxylic acid 1-azabicyclo[2.2.2]oct-3-yl ester 

Downstream Products

• 637744-70-8 (3R)-3-[(3-fluorophenyl)(3,4,5-trifluorobenzyl)carbamoyloxy]-1-(2-phenoxyethyl)-1-azoniacyclo[2.2.2]octane bromide 

Relevant articles and documents

Discovery of novel quaternary ammonium derivatives of (3R)-quinuclidinyl carbamates as potent and long acting muscarinic antagonists

Novel quaternary ammonium derivatives of N,N-disubstituted (3R)-quinuclidinyl carbamates have been identified as potent M3 muscarinic antagonists with long duration of action in an in vivo model of bronchoconstriction. These compounds have also presented a high level of metabolic transformation (human liver microsomes). The synthesis, structure-activity relationships and biological evaluation of these compounds are reported.

Quinuclidine derivatives as M3 antagonists

Qinuclidine derivative of the general formula (I) in the form of single enantiomers or mixtures thereof are useful in the manufacture of a medicament for the prevention and therapy of respiratory diseases such as asthma, chronic obstructive pulmonary dise