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Sildenafil citrate monohydrate
Author(s) -
Yathirajan Hemmige S.,
Nagaraj Basavegowda,
Nagaraja Padmarajaiah,
Bolte Michael
Publication year - 2005
Publication title -
acta crystallographica section e
Language(s) - English
Resource type - Journals
ISSN - 1600-5368
DOI - 10.1107/s1600536805002564
Subject(s) - ring (chemistry) , alkoxy group , hydrogen bond , chemistry , protonation , sildenafil , piperazine , intramolecular force , medicinal chemistry , sulfonyl , benzene , stereochemistry , ion , molecule , organic chemistry , alkyl , medicine
Sildenafil citrate is well known as Viagra for the treatment of erectile dysfuncion. In the title compound (systematic name: 1‐{[3‐(6,7‐Dihydro‐1‐methyl‐7‐oxo‐3‐propyl‐1 H ‐pyrazolo[4,3‐ d ]pyrimidin‐5‐yl)‐4‐ethoxyphenyl]sulfonyl}‐4‐methylpiperazinium citrate monohydrate), C 22 H 31 N 6 O 4 S + ·C 6 H 7 O 7 − ·H 2 O, the pyrazolopyrimidone ring system and the benzene ring are almost coplanar, enabling an intramolecular hydrogen bond between the pyrazolopyrimidone NH group and the O atom of the ethoxy group. One of the N atoms of the piperazine ring is protonated and the citrate molecule exists as an anion. The crystal packing is stabilized by several hydrogen bonds.

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