Chemical Properties
Crystalline Solid
Originator
Dulcolax,Boehringer
Ingelheim,US,1958
Uses
Bisacodyl is used in the inhibition of (Na+K)ATPase, the increase of mucosal PGE2, and the activation of adenyl cyclase in rat intestine studies. It is used as a laxative drug. It is typically prescribed for relief of constipation.
Definition
ChEBI: Bisacodyl is a diarylmethane.
Manufacturing Process
Preparation of (4,4'-Dihydroxy-Diphenyl)-(Pyridyl-2)-Methane
70.0 grams of α-pyridine aldehyde are fed portionwise with stirring and
cooling to a mixture of 200 grams of phenol and 100 cc of concentrated
sulfuric acid. The reaction mixture is allowed to stand for a while with
repeated stirring, whereby it becomes syrupy, neutralized with sodium
carbonate, dissolved in methanol and filtered. The filtrate is introduced into a
large quantity of water and the resulting precipitate is recrystallized from a
methanol/water mixture. Colorless crystals are obtained of MP 254°C. When
using zinc chloride or tin tetrachloride and warming to a temperature of about
50°C, a corresponding result is obtained.
Preparation of Bisacodyl: 5 grams of (4,4'-dihydroxy-diphenyl)-(pyridyl-2)-
methane are heated with 5 grams of anhydrous sodium acetate and 20 cc of
acetic anhydride for three hours over a boiling water bath. The cooled reaction
mixture is poured into water, whereby after a while a colorless substance
precipitates, which is filtered off with suction, washed with water and
recrystallized from aqueous ethanol. Colorless bright crystals, MP 138°C are
obtained.
brand name
Correctol
Tablets, Caplets (Schering-Plough HealthCare); Dulcolax
(Boehringer Ingelheim); Evac-Q-Tabs (Savage); Feen-a-
Mint Tablets (Schering-Plough HealthCare); Modane
(Savage); SK-Bisacodyl (SmithKline Beecham); Theralax
(SmithKline Beecham).
Therapeutic Function
Laxative
Veterinary Drugs and Treatments
Bisacodyl oral and rectal products are used as stimulant cathartics
in dogs and cats.
Metabolism
Bisacodyl is rapidly hydrolysed to the active principle
bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM),
mainly by esterases of the enteric mucosa. After oral
and rectal administration, only small amounts of the
drug are absorbed and are almost completely conjugated
in the intestinal wall and the liver to form the inactive
BHPM glucuronide. Following the administration of
bisacodyl coated tablets, an average of 51.8% of the
dose was recovered in the faeces as free BHPM and an
average of 10.5% of the dose was recovered in the urine
as BHPM glucuronide. Following the administration as a
suppository, an average of 3.1% of the dose was recoveredas BHPM glucuronide in the urine. Stool contained
large amounts of BHPM (90% of the total excretion) in
addition to small amounts of unchanged bisacodyl
