Bisacodyl

Identification

Name
Bisacodyl
Accession Number
DB09020
Description

Bisacodyl is an organic stimulant laxative that acts directly on the colon to promote bowel movement. Bisacodyl is prescribed for constipation, neurogenic bowel dysfunction, and bowel preparation before medical examinations.

Type
Small Molecule
Groups
Approved
Structure
Thumb
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

Indicated for cleansing of the colon as a preparation for colonoscopy in adults.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Bisacodyl is hydrolyzed by intestinal brush border enzymes and colonic bacteria to form an active metabolite [bis-(p-hydroxyphenyl) pyridyl-2 methane; (BHPM)] that acts directly on the colonic mucosa to produce colonic peristalsis.

Mechanism of action

Induces diarrhea which cleanses the colon.

Absorption

15%

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic (CYP450-mediated).

Route of elimination
Not Available
Half-life

16 hours

Clearance

primarily in the feces, systemically absorbed drug is excreted in the urine.

Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Bisacodyl.
AclidiniumThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aclidinium.
AlfentanilThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Alfentanil.
AlloinThe risk or severity of adverse effects can be increased when Bisacodyl is combined with Alloin.
AlmasilateThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Almasilate.
AluminiumThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aluminium.
Aluminium phosphateThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aluminium phosphate.
Aluminum hydroxideThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aluminum hydroxide.
AmantadineThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Amantadine.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Bisacodyl.
Additional Data Available
  • Extended Description
    Extended Description
    Available for Purchase

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action
    Available for Purchase

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Take separate from antacids. Take at least 1 hour before or after antacids and milk.

Products

Purchasing individual compounds or compound libraries for your research?
Learn More
Active Moieties
NameKindUNIICASInChI Key
DeacetylbisacodylunknownR09078E41Y603-41-8LJROKJGQSPMTKB-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BisacodylTablet5 mg/1OralRemedy Repack2010-08-042012-07-01US flag
Magic Bullet Laxative SuppositorySuppositoryRectalSmordins Dispensary Ltd.Not applicableNot applicableCanada flag
Soflax EX Micro-enemaEnema; SuspensionRectalPharmascience IncNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlophenTablet, coated5 mg/1OralNumark Brands, Inc1907-04-15Not applicableUS flag
Alophen TabletsTablet, delayed releaseOralNumark Laboratories, Inc.1998-08-312009-07-31Canada flag
Apo-bisacodylTablet, delayed releaseOralApotex Corporation1982-12-31Not applicableCanada flag
Apo-bisacodyl Sup 10mgSuppositoryRectalApotex Corporation1988-12-31Not applicableCanada flag
Becolax TabletsTablet, delayed releaseOralViva Pharmaceutical Inc.Not applicableNot applicableCanada flag
Best Choice Bisacodyl LaxativeTablet, coated5 mg/1OralBest Choice (Valu Merchandisers Company)2012-11-02Not applicableUS flag
BET-R-PREP BisacodylTablet5 mg/1TopicalSatius Pharmaceuticals, Llc2017-11-18Not applicableUS flag
Bisac-EvacSuppository10 mg/1RectalCardinal Health2011-06-062019-07-31US flag
Bisac-EvacSuppository10 mgRectalGw Pharmaceuticals Ltd.Not applicableNot applicableCanada flag
Bisac-evacSuppository10 mg/1RectalCosette Pharmaceuticals, Inc.1991-05-22Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bekunis DrageesBisacodyl (5 mg) + Sennosides (60 mg) + Sennosides (20 mg) + Sennosides (25 mg)TabletOralRoha Arzneimittel Gmbh1974-12-312009-07-02Canada flag
Bi-peglyteBisacodyl (5 mg) + Polyethylene glycol (59.55 g) + Potassium chloride (0.76 g) + Sodium bicarbonate (1.69 g) + Sodium chloride (1.46 g) + Sodium sulfate (5.74 g)Kit; Powder, for solution; Tablet, delayed releaseOralPendopharm Division Of Pharmascience Inc2010-06-06Not applicableCanada flag
Bicholate LilasBisacodyl (5 mg) + Aloe Vera Leaf (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg)TabletOralSabex Inc1998-10-282009-11-24Canada flag
DulcolaxBisacodyl (5 mg/1) + Bisacodyl (10 mg/1)KitOral; RectalBoehringer Ingelheim2003-04-012014-08-31US flag
DulcolaxBisacodyl (5 mg/1) + Bisacodyl (10 mg/1)KitOral; RectalBoehringer Ingelheim2003-04-012014-08-31US flag
Dyrax-Q TabBisacodyl (5 mg/161mg) + Docusate sodium (16.75 mg/161mg)TabletOralCho-A Pharm.Co.,Ltd.2019-10-25Not applicableUS flag
GaviLyte-H and BisacodylBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium chloride (0.74 g/2L) + Sodium bicarbonate (2.86 g/2L) + Sodium chloride (5.6 g/2L)KitOralLupin Pharmaceuticals, Inc.2015-04-21Not applicableUS flag
Gentlax SBisacodyl (5 mg) + Docusate sodium (50 mg)TabletOralPurdue Pharma2004-10-122011-08-04Canada flag
HalfLytely and BisacodylBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium chloride (0.74 g/2L) + Sodium bicarbonate (2.86 g/2L) + Sodium chloride (5.60 g/2L)KitOralBraintree Laboratories2006-12-312012-12-31US flag
HalfLytely and BisacodylBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium chloride (0.74 g/2L) + Sodium bicarbonate (2.86 g/2L) + Sodium chloride (5.60 g/2L)KitOralBraintree Laboratories2006-12-312012-12-31US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BisacodylBisacodyl (10 mg/1)SuppositoryRectalPhysicians Total Care, Inc.2003-09-042013-01-15US flag
BisacodylBisacodyl (5 mg/1)TabletOralRemedy Repack2010-08-042012-07-01US flag
BisacodylBisacodyl (5 mg/1)TabletOralCardinal Health2011-06-022011-10-31US flag
PCP 100 KitBisacodyl (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)KitOralAsclemed Usa, Inc.2014-01-02Not applicableUS flag

Categories

ATC Codes
A06AB52 — Bisacodyl, combinationsA06AB02 — BisacodylA06AG02 — Bisacodyl
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

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
  1. Stiens SA, Luttrel W, Binard JE: Polyethylene glycol versus vegetable oil based bisacodyl suppositories to initiate side-lying bowel care: a clinical trial in persons with spinal cord injury. Spinal Cord. 1998 Nov;36(11):777-81. [PubMed:9848486]
  2. Wexner SD, Beck DE, Baron TH, Fanelli RD, Hyman N, Shen B, Wasco KE: A consensus document on bowel preparation before colonoscopy: prepared by a task force from the American Society of Colon and Rectal Surgeons (ASCRS), the American Society for Gastrointestinal Endoscopy (ASGE), and the Society of American Gastrointestinal and Endoscopic Surgeons (SAGES). Gastrointest Endosc. 2006 Jun;63(7):894-909. [PubMed:16733101]
  3. 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. [PubMed:9681329]
KEGG Drug
D00245
PubChem Compound
2391
PubChem Substance
310264977
ChemSpider
2299
BindingDB
61400
RxNav
1596
ChEBI
3125
ChEMBL
CHEMBL942
ZINC
ZINC000003830321
Drugs.com
Drugs.com Drug Page
Wikipedia
Bisacodyl
AHFS Codes
  • 56:12.00 — Cathartics and Laxatives
FDA label
Download (62.7 KB)
MSDS
Download (495 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableBowel preparation therapy1
4CompletedNot AvailableColonoscopy1
4CompletedDiagnosticBowel Cleansing Quality1
4CompletedOtherChronic Constipation1
4CompletedPreventionChronic Obstructive Pulmonary Disease (COPD)1
4CompletedPreventionThoracoabdominal Aortic Aneurysms1
4CompletedSupportive CareColonic Motility Index / Constipation1
4CompletedTreatmentColon Cleansing1
4CompletedTreatmentColonoscopy6
4CompletedTreatmentColonoscopy Preparation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral3 mg
TabletTopical5 mg/1
Kit; powder, for solution; tablet, delayed releaseOral
Tablet, delayed releaseOral5 m
SuppositoryRectal0.01 g/2g
TabletOral5 mg
Tablet, coatedOral10 mg
Tablet, delayed releaseOral
Tablet, delayed releaseOral5 mg/1
SuppositoryRectal10 mg/1
Tablet, coatedOral5 mg
SuppositoryRectal10 mg/2000mg
KitOral; Rectal
Tablet, coatedOral5 mg/1
Tablet, delayed release; tablet, film coatedOral
SuspensionRectal
TabletOral
PillOral5 mg/5mg
TabletOral5 mg/5mg
EnemaRectal10 mg/30mL
Capsule5 mg
KitOral
SuppositoryRectal5 mg
SuppositoryRectal10 mg
Tablet, delayed releaseOral5 mg
Tablet
SuppositoryRectal
TabletOral
Enema; suspensionRectal
SuppositoryRectal10 MG/G
TabletOral5 mg/1
Capsule, gelatin coatedOral5 mg/1
Tablet, film coatedOral5 mg/1
Tablet, sugar coatedOral5 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US2764590No1953-03-161973-03-16US flag
US7291324No2007-11-062022-10-22US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)138U.S. Patent 2,764,590.
Predicted Properties
PropertyValueSource
Water Solubility0.00127 mg/mLALOGPS
logP4.71ALOGPS
logP3.61ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)4.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.49 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.15 m3·mol-1ChemAxon
Polarizability38.48 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03e9-0619000000-408a755e5a908f9651a8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-2900000000-44bd4ec7df3de8de29aa

Drug created on June 24, 2014 11:03 / Updated on October 31, 2020 10:29

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates