603-50-9

Crystalline Solid

Dulcolax,Boehringer Ingelheim,US,1958

Cathartic.

Stimulant laxative.

ChEBI: Bisacodyl is a diarylmethane.

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.

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).

Laxative

Laxative

Bisacodyl oral and rectal products are used as stimulant cathartics in dogs and cats.

Potentially hazardous interactions with other drugs
None known

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

Store at 2-8°C