8489. Sildenafil

Nomenclature

CAS number: 139755-83-2
1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine; 5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one; UK-92480.
C22H30N6O4S; mol wt 474.58.
C 55.68%, H 6.37%, N 17.71%, O 13.49%, S 6.76%.

Description and references

Orally active, selective type 5 cGMP phosphodiesterase inhibitor. Prepn: A. S. Bell et al., EP 463756; eidem, US 5250534 (1992, 1993 both to Pfizer). Structure-activity study: N. K. Terrett et al., Bioorg. Med. Chem. Lett. 6, 1819 (1996). Clinical trial in impotence: I. Goldstein et al., N. Engl. J. Med. 338, 1397 (1998). Review of pharmacology: M. Boolell et al., Int. J. Impot. Res. 8, 47-52 (1996); of clinical experience: D. G. Hatzichristou, ibid. 14, Suppl. 1, S43-S52 (2002). Clinical evaluation in pulmonary hypertension: B. K. S. Sastry et al., J. Am. Coll. Cardiol. 43, 1149 (2004).

Chemical structure

Properties

Crystals, mp 187-189°.

Derivative

Citrate.

Nomenclature

CAS number: 171599-83-0
Revatio (Pfizer); Viagra (Pfizer).
C22H30N6O4S.C6H8O7; mol wt 666.70.
C 50.44%, H 5.74%, N 12.61%, O 26.40%, S 4.81%.

Therapeutic Category

In treatment of male erectile dysfunction. Antihypertensive.

Keywords

Phosphodiesterase Inhibitor; Impotence Therapy; Antihypertensive