8712. Solifenacin

Nomenclature

CAS number: 242478-37-1
(1S)-3,4-Dihydro-1-phenyl-2(1H)-isoquinolinecarboxylic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester; (1S,3′R)-3′-quinuclidinyl-1-phenyl-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate.
C23H26N2O2; mol wt 362.46.
C 76.21%, H 7.23%, N 7.73%, O 8.83%.

Description and references

Muscarinic M3 receptor antagoinst. Prepn: M. Takeuchi et al., WO 9620194; eidem, US 6017927 (1996, 2000 both to Yamanouchi). Receptor binding studies: K. Ikeda et al., Arch. Pharmacol. 366, 97 (2002); selectivity profile: A. Ohtake et al., Eur. J. Pharmacol. 492, 243 (2004). Clinical study in overactive bladder: C. R. Chapple et al., Br. J. Urol. 93, 303 (2004); F. Habb et al., Eur. Urol. 47, 376 (2005). Clinical comparison with tolterodine: C. R. Chapple et al., ibid. 48, 464 (2005). Review of efficacy and tolerability studies: S. Brunton, L. Kuritzky, Curr. Med. Res. Opin. 21, 71-80 (2005); of clinical development: C. K. Payne, Drugs 66, 175-190 (2006).

Chemical structure

Properties

Yellow oil.

Derivative

Succinate.

Nomenclature

CAS number: 242478-38-2
YM-905; Vesicare (Yamanouchi).
C23H26N2O2.C4H6O4; mol wt 480.55.
C 67.48%, H 6.71%, N 5.83%, O 19.98%.

Properties

White to slightly yellowish crystals, mp ≈145°. Freely sol in acetic acid, water, methanol, dimethylsulfoxide.

Therapeutic Category

In treatment of urinary incontinence.

Keywords

Antimuscarinic