Bisacodyl

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Cat Number

INT603509

CAS Number

603-50-9

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CAS Number

603-50-9

EINECS

210-044-4

Storage

Store at -20℃

Synonyms

Dulcolax; Bicol; Theralax; 4,4'-(2-Pyridylmethylene)diphenol diacetate

Molecular Formula

C22H19NO4

Molecular Weight

361.4

Smiles

CC(=O)OC1=CC=C(C=C1)C(C2=CC=C(C=C2)OC(=O)C)C3=CC=CC=N3

Appearance

Solid

General Description

Bisacodyl belongs to the class of drugs known as diphenyl methane derivatives. Bisacodyl is a prodrug that is transformed in the intestine into its active metabolite bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM), which is responsible for the laxative effect. Bisacodyl is converted to BHPM through action of endogenous deacetylase enzymes found in the mucosa of the small intestine and colon.

Mechanism of Action

Bisacodyl belongs to a class of laxatives known as stimulant laxatives. It has two primary mechanisms of action. Firstly, after oral ingestion bisacodyl passes through the intestines where it is converted to an active metabolite that directly stimulates colonic myenteric plexus (nerve endings) in the colonic mucosa. Activation of these receptors increases colonic peristalsis which moves the stool into the rectum faster. Secondly, bisacodyl alters electrolyte transport by decreasing absorption of water and stimulating secretion of water into the intestinal lumen.

Application

Bisacodyl is effective for the treatment of several forms of acute and chronic constipation, including constipation in patients with inadequate bowel motility. Because of its high efficacy and reliability of action, Bisacodyl is commonly used for bowel cleansing prior to exams including colonoscopies, X-rays or abdominal surgery. It is also used as a short-term secondary auxiliary treatment for constipation brought on by extended bed rest or medication.

As a stimulant laxative, Bisacodyl has a dual action in both colonic motility and mucosal secretion. Converted into its active form, BHPM causes an increase in smooth muscle activity in the large intestine by directly stimulating the myocytes (likely through L-type calcium channels), increasing tone, and inducing high-amplitude propagating contractions (HAPCs) that speed colonic transit. Additionally, Bisacodyl provokes a pro-secretory effect, mediated by elevated prostaglandin E2 levels which cause inhibition of aquaporin 3 (AQP3) expression. This decrease in AQP3 prevents reabsorption of water from the lumen. Bisacodyl also causes active secretion of Na+, Cl−, and K+ into the intestinal lumen. The net movement of water into the lumen both softens stool and promotes motility.

Fig. 1 Overview of mechanism of laxative action of bisacodyl and sodium picosulfate. (Corsetti M, et al. 2021)

References

Corsetti M, et al. Bisacodyl: a review of pharmacology and clinical evidence to guide use in clinical practice in patients with constipation. Neurogastroenterology & Motility. 2021, 33(10): e14123.

The ionotropic gelation method was used for the preparation of Bisacodyl-loaded chitosan nanoparticles (BSL@CS NPs). The prepared NPs were characterized using FTIR, PXRD, SEM, and TEM which confirmed spherical NPs. Multispectroscopic analysis such as Fluorescence spectroscopy, UV spectroscopy and CD spectroscopy revealed static quenching mechanism and weak binding affinity of NPs for BSA. It also changed the conformation of protein by increasing its hydrophobicity and slightly decreasing alpha-helix content without affecting overall structure of protein. This study could be helpful in elucidating the pharmacokinetics and ADME properties of Bisacodyl drug when administered using nano-carriers.

$Fig. 2 The PXRD diffractogram of the synthesized NPs. (Banu A, <i>et al</i>. 2023)$ Fig. 2 The PXRD diffractogram of the synthesized NPs. (Banu A, et al. 2023)

References

Banu A, et al. Synthesis and characterization of bisacodyl loaded chitosan nanoparticles (BSL@ CS NPs), multispectroscopic study of their interaction with bovine serum albumin (BSA). Journal of Molecular Liquids. 2023, 387: 122488.