Identification
- Summary
Bisacodyl is a stimulant laxative used for the temporary relief of occasional constipation and cleansing of the colon as a preparation for colonoscopy in adults.
- Brand Names
- Alophen Reformulated Jan 2008, Bi-peglyte, Bisac-evac, Carters Little Pills, Dulcolax, Fleet Mineral Oil, Gavilyte-H and Bisacodyl
- Generic Name
- Bisacodyl
- DrugBank Accession Number
- DB09020
- Background
Bisacodyl, a diphenylmethane derivative, is a commonly used over the counter stimulant laxative for occasional constipation.5,9 Both bisacodyl and picosulfate are metabolized to the same active metabolite bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM).4,5,6
Bisacodyl was patented on 25 September 19568 but has been used as a laxative since 1952.5
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Bisacodyl (DB09020)
- Weight
- Average: 361.3906
Monoisotopic: 361.131408101 - Chemical Formula
- C22H19NO4
- Synonyms
- Bisacodilo
- Bisacodyl
- Bisacodyle
- Bisacodylum
- Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate (ester)
- External IDs
- LA 96 a
- LA96a
Pharmacology
- Indication
Bisacodyl is indicated to relieve occasional constipation and irregularity.9
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Constipation Combination Product in combination with: Phenolphthalein (DB04824) •••••••••••• ••••••• •••••• Used in combination to treat Constipation Combination Product in combination with: Docusate (DB11089) •••••••••••• ••••••• ••••••• •••••• Treatment of Occasional constipation ••• ••• •••••••••••• •••••• Treatment of Bowel irregularity ••• ••• •••••••••••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Patients should be counselled regarding abdominal pain, nausea, vomiting, or a change in bowel function that lasts longer than 2 weeks.9 It has a wide therapeutic index, as patients can take 5-15 mg orally.9 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.9 Patients should also be counselled to stop taking the medication if they experience rectal bleeding or no bowel movement in 12 hours.9
- Mechanism of action
Bisacodyl is deacetylated to the active bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM) by an intestinal deacetylase.4,5,6 BHPM can stimulate parasympathetic nerves in the colon directly to increase motility and secretions.5
Bisacodyl stimulates adenylate cyclase, increasing cyclic AMP, leading to active transport of chloride and bicarbonate out of cells.5 Sodium ions, potassium ions, and water passively leave the cell; while sodium and chloride ions are unable to be reabsorbed.5
Water is also be transported from the luminal side of cells into the vasculature by aquaporin 3.7 Bisacodyl decreases expression of aquaporin 3, preventing water from moving into the vasculature, which may contribute to increased water in the colon.7
Bisacodyl directly stimulates parasympathetic nerves in the colon, stimulating contraction of longitudinal smooth muscle but not circular smooth muscle.3,5
Target Actions Organism UAquaporin-3 negative modulatorHumans USodium/Potassium Transporting ATPase inhibitorHumans - Absorption
Oral formulations of bisacodyl are only 16% bioavailable.2,3 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.10 A 10 mg suppository reaches a Cmax of 0-64 ng/mL.10
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.6 After multiple doses, the geometric mean AUC decreases to 311 h*ng/mL.6
- Volume of distribution
Data regarding the volume of distribution of bisacodyl is not readily available. However, the volume of distribution of the active metabolite, BHPM, in lactating women is 181 L after a single dose and 289 L at steady state.6
- Protein binding
Not Available
- Metabolism
Bisacodyl is deacetylated to the active bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM) by an intestinal deacetylase.4,5,6 A small amount of BHPM is absorbed from the gastrointestinal tract, and is glucuronidated before elimination.6
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- Route of elimination
The majority of bisacodyl is eliminated in the feces. 13.8-17.0% of a bisacodyl dose is eliminated in the urine as the active metabolite BHPM.6
- Half-life
Data regarding the half life of bisacodyl is not readily available. The half life of the active metabolite, BHPM, in lactating women was 7.3 h after a single 10 mg oral dose and 10.0 h after multiple doses.6
- Clearance
Data regarding the clearance of bisacodyl is not readily available. The apparent plasma clearance of the active metabolite, BHPM, in lactating women after a single 10 mg oral dose is 272 mL/min and after multiple doses is 412 mL/min.6
- Adverse Effects
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Patients experiencing an overdose of bisacodyl may present with more severe diarrhea and electrolyte imbalance.1 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.10
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The risk or severity of dehydration can be increased when Acetazolamide is combined with Bisacodyl. Aclidinium The therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aclidinium. Alfentanil The therapeutic efficacy of Bisacodyl can be decreased when used in combination with Alfentanil. Alloin The risk or severity of adverse effects can be increased when Bisacodyl is combined with Alloin. Almasilate The therapeutic efficacy of Bisacodyl can be decreased when used in combination with Almasilate. - Food Interactions
- Avoid milk and dairy products. Take at least 1 hour before or after antacids and milk.
- Take separate from antacids. Take at least 1 hour before or after antacids and milk.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Deacetylbisacodyl unknown R09078E41Y 603-41-8 LJROKJGQSPMTKB-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Bisalax (Actavis) / Bolax (Unifarma) / Boots Constipation Relief (Boots) / Derderance (Nisshin Seiyaku) / Dulco-Lax (Boehringer Ingelheim) / Dulcolaxo (Boehringer Ingelheim) / Fleet Laxative (Baxter) / Florisan (Boehringer Ingelheim) / Laxitab (Ranbaxy) / Reliable Gentle Laxative Tablets (Teva) / Spirolax / Verecolene C.M. (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bisacodyl Tablet 5 mg/1 Oral Remedy Repack 2010-08-04 2012-07-01 US 
Magic Bullet Laxative Suppository Suppository 10 mg Rectal Smordins Dispensary Ltd. Not applicable Not applicable Canada 
Soflax EX Micro-enema Enema; Suspension 2 mg / mL Rectal Pharmascience Inc Not applicable Not applicable Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-bisacodyl EC Tablet 5 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Alophen Tablet, coated 5 mg/1 Oral Numark Brands, Inc 1907-04-15 2024-06-01 US Alophen Tablets Tablet, delayed release 5 mg / tab Oral Numark Laboratories, Inc. 1998-08-31 2009-07-31 Canada Amb-bisacodyl Suppository 10 mg Rectal Ambicare Pharmaceuticals Inc. Not applicable Not applicable Canada Apo-bisacodyl Tablet, delayed release 5 mg Oral Apotex Corporation 1982-12-31 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BEKUNIS 3 MG/5 MG KAPLI TABLET, 30 ADET Bisacodyl (3 mg) + Sennosides (5 mg) Tablet, film coated Oral ABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş. 2017-03-10 Not applicable Turkey 
Bekunis Dragees Bisacodyl (5 mg) + Senna leaf (60 mg) + Senna leaf (20 mg) + Senna leaf (25 mg) Tablet Oral Roha Arzneimittel Gmbh 1974-12-31 2009-07-02 Canada Bi-peglyte Bisacodyl (5 mg / tab) + Polyethylene glycol (59.55 g / sachet) + Potassium chloride (0.76 g / sachet) + Sodium bicarbonate (1.69 g / sachet) + Sodium chloride (1.46 g / sachet) + Sodium sulfate (5.74 g / sachet) Kit; Powder, for solution; Tablet, delayed release Oral Pendopharm Division Of Pharmascience Inc 2010-06-06 Not applicable Canada Bicholate Lilas Bisacodyl (5 mg) + Aloe vera leaf (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg) Tablet Oral Sabex Inc 1998-10-28 2009-11-24 Canada CHINTA-LAX Bisacodyl (5 mg) + Docusate sodium (15 mg) Tablet Oral WELLMEX SDN BHD 2020-09-08 2020-12-18 Malaysia 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bisacodyl Bisacodyl (5 mg/1) Tablet Oral Cardinal Health 2011-06-02 2011-10-31 US Bisacodyl Bisacodyl (10 mg/1) Suppository Rectal Physicians Total Care, Inc. 2003-09-04 2013-01-15 US Bisacodyl Bisacodyl (5 mg/1) Tablet Oral Remedy Repack 2010-08-04 2012-07-01 US PCP 100 Kit Bisacodyl (5 mg/1) + Magnesium citrate (1.745 g/29.6mL) + Metoclopramide hydrochloride (10 mg/1) + Petrolatum (0.76 g/1g) + Polyethylene glycol (17 g/17g) Kit Oral Asclemed Usa, Inc. 2014-01-02 Not applicable US
Categories
- ATC Codes
- A06AB52 — Bisacodyl, combinations
- A06AB — Contact laxatives
- A06A — DRUGS FOR CONSTIPATION
- A06 — DRUGS FOR CONSTIPATION
- A — ALIMENTARY TRACT AND METABOLISM
- A06AB — Contact laxatives
- A06A — DRUGS FOR CONSTIPATION
- A06 — DRUGS FOR CONSTIPATION
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Phenol esters / Phenoxy compounds / Pyridines and derivatives / Dicarboxylic acids and derivatives / Heteroaromatic compounds / Carboxylic acid esters / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides show 2 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Diphenylmethane / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound show 9 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 10X0709Y6I
- CAS number
- 603-50-9
- InChI Key
- KHOITXIGCFIULA-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H19NO4/c1-15(24)26-19-10-6-17(7-11-19)22(21-5-3-4-14-23-21)18-8-12-20(13-9-18)27-16(2)25/h3-14,22H,1-2H3
- IUPAC Name
- 4-{[4-(acetyloxy)phenyl](pyridin-2-yl)methyl}phenyl acetate
- SMILES
- CC(=O)OC1=CC=C(C=C1)C(C1=CC=C(OC(C)=O)C=C1)C1=CC=CC=N1
References
- Synthesis Reference
U.S. Patent 2,764,590.
- General References
- Kudo K, Miyazaki C, Kadoya R, Imamura T, Jitsufuchi N, Ikeda N: Laxative poisoning: toxicological analysis of bisacodyl and its metabolite in urine, serum, and stool. J Anal Toxicol. 1998 Jul-Aug;22(4):274-8. [Article]
- Roth W, Beschke K: [Pharmacokinetics and laxative effect of bisacodyl following administration of various dosage forms]. Arzneimittelforschung. 1988 Apr;38(4):570-4. [Article]
- Manabe N, Cremonini F, Camilleri M, Sandborn WJ, Burton DD: Effects of bisacodyl on ascending colon emptying and overall colonic transit in healthy volunteers. Aliment Pharmacol Ther. 2009 Nov 1;30(9):930-6. doi: 10.1111/j.1365-2036.2009.04118.x. Epub 2009 Aug 12. [Article]
- Krueger D, Demir IE, Ceyhan GO, Zeller F, Schemann M: bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM)-the active metabolite of the laxatives bisacodyl and sodium picosulfate-enhances contractility and secretion in human intestine in vitro. Neurogastroenterol Motil. 2018 Jul;30(7):e13311. doi: 10.1111/nmo.13311. Epub 2018 Feb 14. [Article]
- Lawrensia S, Raja A: Bisacodyl . [Article]
- Friedrich C, Richter E, Trommeshauser D, de Kruif S, van Iersel T, Mandel K, Gessner U: Absence of excretion of the active moiety of bisacodyl and sodium picosulfate into human breast milk: an open-label, parallel-group, multiple-dose study in healthy lactating women. Drug Metab Pharmacokinet. 2011;26(5):458-64. doi: 10.2133/dmpk.dmpk-11-rg-007. Epub 2011 Jun 21. [Article]
- Ikarashi N, Baba K, Ushiki T, Kon R, Mimura A, Toda T, Ishii M, Ochiai W, Sugiyama K: The laxative effect of bisacodyl is attributable to decreased aquaporin-3 expression in the colon induced by increased PGE2 secretion from macrophages. Am J Physiol Gastrointest Liver Physiol. 2011 Nov;301(5):G887-95. doi: 10.1152/ajpgi.00286.2011. Epub 2011 Aug 25. [Article]
- US Patent: US2764590 [Link]
- DailyMed:Bet-R-Prep (Bisacodyl) Oral Tablet [Link]
- FDA Pharmacology Review: HalfLytely (Polyethylene Glycol-3350, Sodium Chloride, Sodium Bicarbonate, Potassium Chloride) Oral Solution and Bisacodyl Oral Tablet [Link]
- External Links
- FDA label
- Download (62.7 KB)
- MSDS
- Download (495 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Bowel preparation therapy 1 4 Completed Not Available Colonoscopy 1 4 Completed Diagnostic Bowel Cleansing Quality 1 4 Completed Other Chronic Constipation 1 4 Completed Prevention Chronic Obstructive Pulmonary Disease (COPD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral Tablet Topical 5 mg/1 Kit; powder, for solution; tablet, delayed release Oral Tablet, delayed release Oral 500000 mg Suppository Rectal 0.01 g/2g Tablet, delayed release Oral 5 mg/1 Tablet; tablet, delayed release Oral 5 MG Suppository Rectal 10 mg/1 Suppository Rectal 5.0 mg Tablet, delayed release Oral 5 mg / tab Tablet Oral 5.0 mg Tablet, coated Oral 5 mg Suppository Rectal 10 mg Suppository Rectal 5 mg Kit Oral; Rectal Tablet Oral 5.000 mg Tablet, coated Oral 5 mg/1 Tablet, delayed release; tablet, film coated Oral Tablet, coated Oral Suppository Rectal Suspension Rectal 10 mg / 5 mL Tablet, film coated Oral 5 mg/1 Suppository Rectal 0.01 g Tablet, coated Oral 5.0000 mg Tablet 5 mg Tablet Oral Pill Oral 5 mg/5mg Tablet Oral 5 mg/5mg Enema Rectal 10 mg/30mL Kit Oral Tablet Suppository Rectal 10 mg / sup Tablet, film coated Oral 5 mg Tablet Oral Tablet Oral 5 mg Cream; kit; powder, for solution; tablet, coated Oral; Rectal Suppository Rectal 10 mg/2000mg Tablet, delayed release Oral Enema; suspension Rectal 2 mg / mL Suppository Rectal 10 MG/G Tablet Oral 5 mg/1 Capsule, gelatin coated Oral 5 mg/1 Tablet, delayed release Oral 25 mg/1 Tablet, sugar coated Oral 5 mg/1 Tablet, coated Oral Tablet, sugar coated Oral 5 mg Tablet, coated Oral 10 mg Tablet, delayed release Oral 5 mg Capsule - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US2764590 No 1953-03-16 1973-03-16 US US7291324 No 2007-11-06 2022-10-22 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 138 U.S. Patent 2,764,590. - Predicted Properties
Property Value Source Water Solubility 0.00127 mg/mL ALOGPS logP 4.71 ALOGPS logP 3.61 Chemaxon logS -5.5 ALOGPS pKa (Strongest Basic) 4.08 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 65.49 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 100.15 m3·mol-1 Chemaxon Polarizability 38.48 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 212.2066588 predictedDarkChem Lite v0.1.0 [M-H]- 181.63408 predictedDeepCCS 1.0 (2019) [M+H]+ 212.2700588 predictedDarkChem Lite v0.1.0 [M+H]+ 183.9921 predictedDeepCCS 1.0 (2019) [M+Na]+ 212.8560588 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.54608 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Negative modulator
- General Function
- Water channel required to promote glycerol permeability and water transport across cell membranes. Acts as a glycerol transporter in skin and plays an important role in regulating SC (stratum corneum) and epidermal glycerol content. Involved in skin hydration, wound healing, and tumorigenesis. Provides kidney medullary collecting duct with high permeability to water, thereby permitting water to move in the direction of an osmotic gradient. Slightly permeable to urea and may function as a water and urea exit mechanism in antidiuresis in collecting duct cells. It may play an important role in gastrointestinal tract water transport and in glycerol metabolism (By similarity).
- Specific Function
- Glycerol channel activity
- Gene Name
- AQP3
- Uniprot ID
- Q92482
- Uniprot Name
- Aquaporin-3
- Molecular Weight
- 31543.605 Da
References
- Ikarashi N, Baba K, Ushiki T, Kon R, Mimura A, Toda T, Ishii M, Ochiai W, Sugiyama K: The laxative effect of bisacodyl is attributable to decreased aquaporin-3 expression in the colon induced by increased PGE2 secretion from macrophages. Am J Physiol Gastrointest Liver Physiol. 2011 Nov;301(5):G887-95. doi: 10.1152/ajpgi.00286.2011. Epub 2011 Aug 25. [Article]
- Rachmilewitz D, Karmeli F, Okon E: Effects of bisacodyl on cAMP and prostaglandin E2 contents, (Na + K) ATPase, adenyl cyclase, and phosphodiesterase activities of rat intestine. Dig Dis Sci. 1980 Aug;25(8):602-8. doi: 10.1007/BF01318874. [Article]
- Schreiner J, Nell G, Loeschke K: Effect of diphenolic laxatives on Na+-K+-activated ATPase and cyclic nucleotide content of rat colon mucosa in vivo. Naunyn Schmiedebergs Arch Pharmacol. 1980 Sep;313(3):249-55. doi: 10.1007/BF00505741. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hormone binding
- Specific Function
- This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates th...
Components:
References
- Schreiner J, Nell G, Loeschke K: Effect of diphenolic laxatives on Na+-K+-activated ATPase and cyclic nucleotide content of rat colon mucosa in vivo. Naunyn Schmiedebergs Arch Pharmacol. 1980 Sep;313(3):249-55. doi: 10.1007/BF00505741. [Article]
Drug created at June 24, 2014 17:03 / Updated at February 20, 2024 23:55