Bisacodyl

Identification

Name
Bisacodyl
Accession Number
DB09020
Type
Small Molecule
Groups
Approved
Description

Bisacodyl is an organic compound that is used as a stimulant laxative drug. It works directly on the colon to produce a bowel movement. It is typically prescribed for relief of constipation and for the management of neurogenic bowel dysfunction as well as part of bowel preparation before medical examinations, such as for a colonoscopy.

Structure
Thumb
Synonyms
  • Bisacodilo
  • Bisacodyl
  • Bisacodyle
  • Bisacodylum
  • Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate (ester)
  • Spirolax
External IDs
La 96 a
Active Moieties
NameKindUNIICASInChI Key
DeacetylbisacodylunknownR09078E41Y603-41-8LJROKJGQSPMTKB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Magic Bullet Laxative SuppositorySuppository10 mgRectalSmordins Dispensary Ltd.Not applicableNot applicableCanada
Soflax EX Micro-enemaEnema; Suspension2 mgRectalPharmascience IncNot applicableNot applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlophenTablet, coated5 mg/1OralNumark Brands, Inc1907-04-15Not applicableUs
Alophen TabletsTablet, delayed release5 mgOralNumark Laboratories, Inc.1998-08-312009-07-31Canada
Apo-bisacodylTablet, delayed release5 mgOralApotex Corporation1982-12-31Not applicableCanada
Apo-bisacodyl Sup 10mgSuppository10 mgRectalApotex Corporation1988-12-31Not applicableCanada
Becolax TabletsTablet, delayed release5 mgOralViva Pharmaceutical Inc.Not applicableNot applicableCanada
Best Choice Bisacodyl LaxativeTablet, coated5 mg/1OralValu Merchandisers Company (Best Choice)2012-11-02Not applicableUs
BET-R-PREP BisacodylTablet5 mg/1TopicalSatius Pharmaceuticals, Llc2017-11-18Not applicableUs
Bisac-evacSuppository10 mg/1RectalGw Pharmaceuticals Ltd.1991-05-22Not applicableUs
Bisac-EvacSuppository10 mgRectalGw Pharmaceuticals Ltd.Not applicableNot applicableCanada
Bisac-EvacSuppository10 mg/1RectalCardinal Health2011-06-06Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bekunis DrageesBisacodyl (5 mg) + Sennosides (20 mg) + Sennosides (25 mg) + Sennosides (60 mg)TabletOralRoha Arzneimittel Gmbh1974-12-312009-07-02Canada
Bi-peglyteBisacodyl (5 mg) + Polyethylene glycol (59.55 g) + Potassium Chloride (0.76 g) + Sodium Chloride (1.46 g) + Sodium bicarbonate (1.69 g) + Sodium sulfate (5.74 g)Kit; Powder, for solution; Tablet, delayed releaseOralPendopharm Division Of De Pharmascience Inc2010-06-06Not applicableCanada
DulcolaxBisacodyl (5 mg/1) + Bisacodyl (10 mg/1)KitBoehringer Ingelheim2003-04-012014-08-31Us
DulcolaxBisacodyl (5 mg/1) + Bisacodyl (10 mg/1)KitBoehringer Ingelheim2003-04-012014-08-31Us
GaviLyte-H and BisacodylBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium Chloride (0.74 g/2L) + Sodium Chloride (5.6 g/2L) + Sodium bicarbonate (2.86 g/2L)KitOralGavis Pharmaceuticals, LLC.2015-04-21Not applicableUs
Gentlax SBisacodyl (5 mg) + Docusate sodium (50 mg)TabletOralPurdue Pharma2004-10-122011-08-04Canada
HalfLytely and BisacodylBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium Chloride (0.74 g/2L) + Sodium Chloride (5.60 g/2L) + Sodium bicarbonate (2.86 g/2L)KitOralBraintree Laboratories2006-12-312012-12-31Us
HalfLytely and BisacodylBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium Chloride (0.74 g/2L) + Sodium Chloride (5.60 g/2L) + Sodium bicarbonate (2.86 g/2L)KitOralBraintree Laboratories2006-12-312012-12-31Us
HalfLytely and Bisacodyl Bowel Prep with Flavor PacksBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium Chloride (0.74 g/2L) + Sodium Chloride (5.60 g/2L) + Sodium bicarbonate (2.86 g/2L)KitOralBraintree Laboratories2010-08-022013-06-28Us
Poly-PrepBisacodyl (5 mg/1) + Hydrocortisone acetate (5 mg/1g) + Lidocaine hydrochloride (30 mg/1g) + Polyethylene glycol (17 g/17g)KitPure Tek Corporation2017-01-10Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BisacodylBisacodyl (5 mg/1)TabletOralRemedy Repack2010-08-042012-07-01Us
PCP 100 KitBisacodyl (5 mg/1) + Magnesium citrate (1.745 g/29.6mL) + Metoclopramide hydrochloride monohydrate (10 mg/1) + Petrolatum (0.76 g/1g) + Polyethylene glycol (17 g/17g)KitOral; TopicalAsclemed Usa, Inc.2014-01-02Not applicableUs
International/Other Brands
Bisalax (Actavis) / Bolax (Unifarma) / Boots Constipation Relief (Boots) / Derderance (Nisshin Seiyaku) / Dulco-Lax (Boehringer Ingelheim) / Dulcolax / Dulcolaxo (Boehringer Ingelheim) / Fleet Laxative (Baxter) / Florisan (Boehringer Ingelheim) / Laxitab (Ranbaxy) / Reliable Gentle Laxative Tablets (Teva) / Verecolene C.M. (GlaxoSmithKline)
Categories
UNII
10X0709Y6I
CAS number
603-50-9
Weight
Average: 361.3906
Monoisotopic: 361.131408101
Chemical Formula
C22H19NO4
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

Pharmacology

Indication

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

Associated Conditions
Associated Therapies
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.

Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(2-benzhydryloxyethyl)diethyl-methylammonium iodideThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
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.
AgmatineThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Agmatine.
AlfentanilThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Alfentanil.
AlmasilateThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Almasilate.
AloglutamolThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aloglutamol.
AlphacetylmethadolThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Alphacetylmethadol.
AlphaprodineThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Alphaprodine.
AluminiumThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aluminium.
Food Interactions
Not Available

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]
External Links
KEGG Drug
D00245
PubChem Compound
2391
PubChem Substance
310264977
ChemSpider
2299
BindingDB
61400
ChEBI
3125
ChEMBL
CHEMBL942
Drugs.com
Drugs.com Drug Page
Wikipedia
Bisacodyl
ATC Codes
A06AB52 — Bisacodyl, combinationsA06AB02 — BisacodylA06AG02 — Bisacodyl
AHFS Codes
  • 56:12.00 — Cathartics and Laxatives
FDA label
Download (62.7 KB)
MSDS
Download (495 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1, 2RecruitingTreatmentHemangioma Liver1
2CompletedTreatmentAbdominal Pain (AP) / Post-Operative Nausea and Vomiting (PONV)1
2CompletedTreatmentOccasional Constipation1
2RecruitingTreatmentDisseminated Sclerosis / Incontinence, Fecal / Occasional Constipation1
2WithdrawnTreatmentBowel preparation therapy1
3CompletedNot AvailableBowel Diseases / Colon Adenomas1
3CompletedDiagnosticBowel Preparation Before Colonoscopy / Healthy Persons1
3CompletedDiagnosticColon Capsule Completion Rates / Colon Capsule Polyp Detection / Quality of Bowel Preparation for the Colon Capsule1
3CompletedTreatmentBowel preparation therapy2
3CompletedTreatmentChronic Constipation1
3CompletedTreatmentOccasional Constipation2
3Unknown StatusNot AvailableMalignant Neoplasm of Colon1
4CompletedNot AvailableBowel preparation therapy1
4CompletedNot AvailableColonoscopy1
4CompletedDiagnosticBowel Cleansing Quality1
4CompletedDiagnosticColonoscopy1
4CompletedOtherChronic Constipation1
4CompletedSupportive CareColonic Motility Index / Occasional Constipation1
4CompletedTreatmentColonoscopy1
4CompletedTreatmentColonoscopy Preparation1
4CompletedTreatmentColorectal Cleansing Prior Operation1
4CompletedTreatmentGastrointestinal Complications1
4CompletedTreatmentGeneral Surgery / Ileus / Occasional Constipation1
4CompletedTreatmentIntestinal Cancer1
4CompletedTreatmentOpioid Induced Constipation (OIC)1
4CompletedTreatmentPreparation for Colonoscopy1
4CompletedTreatmentSubjets Requiring a Colonoscopy1
4CompletedTreatmentPostoperative paralytic ileus1
4RecruitingPreventionOccasional Constipation1
4RecruitingTreatmentHospitalized Patients1
4TerminatedDiagnosticColonoscopy Failure / Poor Bowel Preparation1
4Unknown StatusTreatmentBowel Preparation Solutions / Endoscopy1
4Unknown StatusTreatmentBowel Preparation for Colonoscopy1
Not AvailableCompletedDiagnosticColorectal Cancer Screening1
Not AvailableCompletedDiagnosticDiabetes Mellitus (DM)1
Not AvailableCompletedPreventionFunctional Disorder of Intestine1
Not AvailableCompletedScreeningColorectal Cancers1
Not AvailableCompletedTreatmentAutistic Disorder / Encopresis1
Not AvailableRecruitingDiagnosticBowel preparation therapy1
Not AvailableRecruitingDiagnosticConstipation - Functional / Irritable Bowel Syndrome Characterized by Constipation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletTopical5 mg/1
Kit; powder, for solution; tablet, delayed releaseOral
SuppositoryRectal0.01 g/2g
Tablet, delayed releaseOral5 mg/1
SuppositoryRectal10 mg/1
TabletOral5.0 mg
Tablet, delayed releaseOral5 mg
SuppositoryRectal10 mg/2000mg
Kit
SuppositoryRectal5 mg
Tablet, coatedOral5 mg/1
SuspensionRectal10 mg
PillOral5 mg/5mg
TabletOral5 mg/5mg
EnemaRectal10 mg/30mL
TabletOral
KitOral
KitOral; Topical
SuppositoryRectal10 mg
TabletOral5 mg
KitOral; Rectal
Enema; suspensionRectal2 mg
TabletOral5 mg/1
Capsule, gelatin coatedOral5 mg/1
Tablet, sugar coatedOral5 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US2764590No1953-03-161973-03-16Us
US7291324No2002-10-222022-10-22Us

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

Taxonomy

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
Diphenylmethane / Phenol ester / Phenoxy compound / Dicarboxylic acid or derivatives / Pyridine / Heteroaromatic compound / Carboxylic acid ester / Azacycle / Organoheterocyclic compound / Carboxylic acid derivative
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on June 24, 2014 11:03 / Updated on October 16, 2018 08:40