2825. Darifenacin

Nomenclature

CAS number: 133099-04-4
(3S)-1-[2-(2,3-Dihydro-5-benzofuranyl)ethyl]-α,α-diphenyl-3-pyrrolidineacetamide; 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine; (S)-2-[1-[2-(2,3,-dihydrobenzfuran-5-yl)ethyl]-3-pyrrolidinyl]-2,2-diphenylacetamide; UK-88525.
C28H30N2O2; mol wt 426.55.
C 78.84%, H 7.09%, N 6.57%, O 7.50%.

Description and references

Selective muscarinic M3-receptor antagonist. Prepn: P. E. Cross, A. R. MacKenzie, EP 388054; eidem, US 5096890 (1990, 1992 both to Pfizer). HPLC/MS determn in plasma: B. Kaye et al., Anal. Chem. 68, 1658 (1996). Binding profile for receptor subtypes: C. M. Smith, R. W. Wallis, J. Recept. Signal Transduct. Res. 17, 177 (1997); and pharmacology: R. M. Wallis, C. M. Napier, Life Sci. 64, 395 (1999). Pharmacokinetics and metabolism: K. C. Beaumont et al., Xenobiotica 28, 63 (1998). Clinical trial in overactive bladder: F. Haab et al., Eur. Urol. 45, 420 (2004). Review of clinical experience: C. R. Chapple, Expert Opin. Invest. Drugs 13, 1493-1500 (2004).

Chemical structure

Properties

Foam or colorless glass. [α]25D -20.6° (c = 1.0 in methylene chloride). pKa (25°): 9.2.

Derivative

Hydrobromide.

Nomenclature

CAS number: 133099-07-7
Emselex (Novartis); Enablex (Novartis).
C28H31N2O2Br; mol wt 507.46.
C 66.27%, H 6.16%, N 5.52%, O 6.31%, Br 15.75%.

Properties

mp 229°. [α]25D -30.3° (c = 1.0 in methylene chloride). Soly at 37° (mg/ml): water 6.03.

Therapeutic Category

Antispasmodic; in treatment of urinary incontinence.

Keywords

Antispasmodic; Antimuscarinic