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HomeProduct name listBisacodyl

Bisacodyl

Synonym(s):4,4′-(2-pyridylmethylene)-bisphenol diacetate;Bisacodyl

  • CAS NO.:603-50-9
  • Empirical Formula: C22H19NO4
  • Molecular Weight: 361.39
  • MDL number: MFCD00038039
  • EINECS: 210-044-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-04 20:04:50
Bisacodyl Structural

What is Bisacodyl?

Absorption

Oral formulations of bisacodyl are only 16% bioavailable. A 10 mg enteric coated oral tablet reaches a Cmax of 26 ng/mL with a Tmax of 8 hours, while a 10 mg oral solution reaches a Cmax of 237 ng/mL with a Tmax of 1.7 hours. A 10 mg suppository reaches a Cmax of 0-64 ng/mL.
In lactating women, 10mg of oral bisacodyl reaches a Cmax of 20.5-195 ng/mL, with a Tmax of 3-4 hours, and a geometric mean AUC after a single dose of 471 h*ng/mL. After multiple doses, the geometric mean AUC decreases to 311 h*ng/mL.

Toxicity

Patients experiencing an overdose of bisacodyl may present with more severe diarrhea and electrolyte imbalance. Patients should be treated with symptomatic and supportive measures.
The oral LD50 in rats is 4320 mg/kg, and in mice is 17500 mg/kg.

Chemical properties

Crystalline Solid

Originator

Dulcolax,Boehringer Ingelheim,US,1958

The Uses of Bisacodyl

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.

The Uses of Bisacodyl

Cathartic.

The Uses of Bisacodyl

Stimulant laxative.

Indications

Bisacodyl is indicated to relieve occasional constipation and irregularity.

Background

Bisacodyl, a diphenylmethane derivative, is a commonly used over the counter stimulant laxative for occasional constipation. Both bisacodyl and picosulfate are metabolized to the same active metabolite bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM).
Bisacodyl was patented on 25 September 1956 but has been used as a laxative since 1952.

What are the applications of Application

Bisacodyl is a hygroscopic diphenol

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

Pharmacokinetics

Patients should be counselled regarding abdominal pain, nausea, vomiting, or a change in bowel function that lasts longer than 2 weeks. It has a wide therapeutic index, as patients can take 5-15 mg orally. Patients taking bisacodyl should be counselled before taking the medication if they are already experiencing abdominal pain, nausea, vomiting, or a change in bowel function lasting longer than 2 weeks. Patients should also be counselled to stop taking the medication if they experience rectal bleeding or no bowel movement in 12 hours.

Clinical Use

Laxative

Veterinary Drugs and Treatments

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

Metabolism

Bisacodyl is deacetylated to the active bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM) by an intestinal deacetylase. A small amount of BHPM is absorbed from the gastrointestinal tract, and is glucuronidated before elimination.

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

Properties of Bisacodyl

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.
form  neat
pka 4.69±0.10(Predicted)
form  Solid
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.
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 information for Bisacodyl

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Bisacodyl

InChIKey KHOITXIGCFIULA-UHFFFAOYSA-N

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