Bisacodyl Property

Melting point:

138°C

Boiling point:

493.21°C (rough estimate)

Density 

1.2545 (rough estimate)

refractive index 

1.5614 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute mineral acids.

pka

4.69±0.10(Predicted)

color 

White to Off-White

Water Solubility 

Soluble in alcohol (slightly), ether (slightly), chloroform, and acetone. Insoluble in water.

λmax

220nm(MeOH)(lit.)

Merck 

14,1242

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

KHOITXIGCFIULA-UHFFFAOYSA-N

LogP

3.453 (est)

CAS DataBase Reference

603-50-9(CAS DataBase Reference)

NIST Chemistry Reference

Bisacodyl(603-50-9)

EPA Substance Registry System

Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate (ester) (603-50-9)

Safety

Hazard Codes 

Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

SM8750000

TSCA 

Yes

HS Code 

2933399090

Hazardous Substances Data

603-50-9(Hazardous Substances Data)

Toxicity

LD50 orally in rats: >3 g/kg (Schmidt)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Bisacodyl Chemical Properties,Usage,Production

Chemical Properties

Crystalline Solid

Originator

Dulcolax,Boehringer Ingelheim,US,1958

Uses

Cathartic.

Uses

Stimulant laxative.

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

Clinical Use

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