U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H19NO4
Molecular Weight 361.3906
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BISACODYL

SMILES

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

InChI

InChIKey=KHOITXIGCFIULA-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H19NO4
Molecular Weight 361.3906
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Bisacodyl 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. Some drugs (e.g., diuretics, angiotensin converting enzyme inhibitors, angiotensin receptor blockers, or non-steroidal anti-inflammatory drugs) increase risk due to fluid and electrolyte changes. Most common adverse reactions (> 3%) are overall discomfort, abdominal fullness, abdominal cramping, nausea, and vomiting.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
HALFLYTELY

Approved Use

HalfLytely is indicated for cleansing of the colon as a preparation for colonoscopy in adults.

Launch Date

2004
PubMed

PubMed

TitleDatePubMed
Comparison of three forms of bowel preparations for screening flexible sigmoidoscopy.
2001 Jul-Aug
[Laxative effect of poly(ethylene oxide) 1500 per se and in combination with bisacodyl].
2001 Sep-Oct
Optimisation of colon cleansing prior to computed tomographic colonography.
2002 Dec
Low-salt bowel cleansing preparation (LoSo Prep) as preparation for colonoscopy: a pilot study.
2002 Jul
A high-fibre diet in combination with bisacodyl for bowel preparation in gallium renal scintigraphy.
2003 Aug
[Comparison of the effectiveness and tolerability of the saccharosum-sennosid-B solution and sodium-picosulfate in preparation for colonoscopy. Prospective, multicenter, randomized study].
2003 Aug 10
A randomized single-blind trial of whole versus split-dose polyethylene glycol-electrolyte solution for colonoscopy preparation.
2003 Jul
A randomized prospective trial of bowel preparation for colonoscopy with Fortrans compared with bisacodyl.
2003 Jun
Is chronic use of stimulant laxatives harmful to the colon?
2003 May-Jun
Oral sodium phosphate compared with water enemas combined with bisacodyl as bowel preparation for elective colonoscopy.
2003 Oct
Comparison of reduced volume versus four liters sulfate-free electrolyte lavage solutions for colonoscopy colon cleansing.
2003 Oct
Current treatment options for chronic constipation.
2004
Physiologic effects of bowel preparation.
2004 Aug
Results of 24-h manometric recording of colonic motor activity with endoluminal instillation of bisacodyl in patients with severe chronic slow transit constipation.
2004 Aug
If it is inert, why does it move?
2004 Aug
Effect of four-day psyllium supplementation on bowel preparation for colonoscopy:A prospective double blind randomized trial [ISRCTN76623768].
2004 Feb 2
Melanosis coli?
2004 Jan 8
A quality improvement project comparing two regimens of medication for colonoscopy preparation.
2004 Jan-Feb
Management of constipation in residents with dementia: sorbitol effectiveness and cost.
2004 Jul-Aug
[Two cases of ammonium acid urate urinary stones related to anorexia nervosa and laxative abuse].
2004 Mar
Reasons for poor colonic preparation with inpatients.
2004 May-Jun
Bowel preparation of outpatients for intravenous urography: efficacy of castor oil versus bisacodyl.
2005 Apr
[Therapeutic options of chronic constipation].
2005 Dec
Randomized single blind trial of two low-volume bowel preparations for screening computed tomographic colonography.
2005 Jan-Feb
[Constipation: Initial evaluation and diagnostic approach].
2005 Jul-Sep
CT colonography after fecal tagging with a reduced cathartic cleansing and a reduced volume of barium.
2005 Jun
CT colonography with fecal tagging after incomplete colonoscopy.
2005 Jun
Efficacy of bowel preparation with the use of a prepackaged, low fibre diet with a low sodium, magnesium citrate cathartic vs. a clear liquid diet with a standard sodium phosphate cathartic.
2005 Jun 15
Management of constipation in residents with dementia: sorbitol effectiveness and cost.
2005 May-Jun
What is the role of mechanical bowel preparation in patients with pilonidal sinus undergoing surgery? Prospective, randomized, surgeon-blinded trial.
2005 Nov
Colonic ischemia with laxative use in young adults.
2005 Sep
Optimizing use of opiates in the management of cancer pain.
2006 Dec
Bowel preparation for CT-colonography: comparison of two different cleansing protocols.
2006 Dec
A prospective study comparing oral sodium phosphate solution to a bowel cleansing preparation with nutrition food package in children.
2006 Feb
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).
2006 Jun
Polyethylene glycol, unique among laxatives, suppresses aberrant crypt foci, by elimination of cells.
2006 Jun
The bowel cleansing for colonoscopy. A randomized trial comparing three methods.
2006 Mar-Apr
Which is the optimal bowel preparation for colonoscopy - a meta-analysis.
2006 May
Development and validation of three stability-indicating methods for determination of bisacodyl in pure form and pharmaceutical preparations.
2007 Jan-Feb
Fundamental elements for successful performance of CT colonography (virtual colonoscopy).
2007 Jul-Aug
Purple urine bag syndrome in geriatric wards: two faces of a coin?
2007 Oct
[Treatment with bisacodyl, picosulfate and prokinetics. Physiopathology and diagnosis of constipation].
2008
Association of potentially inappropriate medication use with adverse outcomes in ambulatory elderly patients with chronic diseases: experience in a Taiwanese medical setting.
2008
The timing of colonoscopy preparation makes all the difference in the final outcome.
2008 Apr
CT colonography with limited bowel preparation: performance characteristics in an increased-risk population.
2008 Apr
Management of the poorly prepared colonoscopy patient: colonoscopic colon enemas as a preparation for colonoscopy.
2008 Apr
Prospective evaluation of small bowel preparation with bisacodyl and sodium phosphate for capsule endoscopy.
2008 Apr 7
Safety and efficacy of oral low-volume sodium phosphate bowel preparation for colonoscopy in dogs.
2008 Jan-Feb
Comparison of two column characterisation systems based on pharmaceutical applications.
2008 May 2
Electronic colon-cleansing for CT colonography: diagnostic performance.
2009 May-Jun
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Bisacodyl (Dulcolax Suppositories) can be also given as 1 suppository in a single daily dose.
One 5 mg tablet with water or HalfLytely powder dissolved in 2 liters of water.
Route of Administration: Oral
Isolated smooth muscle strips of human colon were mounted in a standardized organ bath system (37°C, basal resting tension 20 mN). The active metabolite of bisacodyl, bishydroxyphenyl-pyridyl-methan (BHPM) was added to the strips and dose-dependently induced tonic contractions. BHPM (150 ug/ml) decreased maximum contraction amplitudes of carbachol by 56± 19% of longitudinal and by 96±4% of circular strips.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:14:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:14:58 GMT 2023
Record UNII
10X0709Y6I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BISACODYL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
BISACODYL [ORANGE BOOK]
Common Name English
FEEN-A-MINT TABLETS
Brand Name English
PHENOL, 4,4'-(2-PYRIDINYLMETHYLENE)BIS-, DIACETATE (ESTER)
Common Name English
Bisacodyl [WHO-DD]
Common Name English
NSC-755914
Code English
BISACODYL [MART.]
Common Name English
BISACODYL [HSDB]
Common Name English
BISACODYL [USP MONOGRAPH]
Common Name English
BISACODYL [EP MONOGRAPH]
Common Name English
BISACODYL [JAN]
Common Name English
bisacodyl [INN]
Common Name English
SK-BISACODYL
Brand Name English
BISACODYL [USP-RS]
Common Name English
4,4'-(2-PYRIDYLMETHYLENE)DIPHENOL DIACETATE (ESTER)
Common Name English
CORRECTOL TABLETS, CAPLETS
Brand Name English
EVAC-Q-TABS
Brand Name English
MODANE
Brand Name English
BISACODYL [MI]
Common Name English
THERALAX
Brand Name English
BISACODYL COMPONENT OF HALFLYTELY
Common Name English
HALFLYTELY COMPONENT BISACODYL
Common Name English
DULCOLAX
Brand Name English
BISACODYL [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QA06AG02
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
WHO-ATC A06AG02
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
WHO-ATC A06AB02
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
NDF-RT N0000009871
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
WHO-VATC QA06AB52
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
WHO-VATC QA06AB02
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
WHO-ATC A06AB52
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
NCI_THESAURUS C29697
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
LIVERTOX NBK548124
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
WHO-ATC A06AB20
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
NDF-RT N0000009371
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
NDF-RT N0000175812
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL942
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
MERCK INDEX
m2516
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1074007
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
INN
824
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
CAS
603-50-9
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
210-044-4
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
PUBCHEM
2391
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
DAILYMED
10X0709Y6I
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
MESH
D001726
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
RXCUI
1596
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
BISACODYL
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
EVMPD
SUB05846MIG
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
DRUG CENTRAL
375
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
NCI_THESAURUS
C28870
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
NSC
755914
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
FDA UNII
10X0709Y6I
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
SMS_ID
100000091949
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
HSDB
3016
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
DRUG BANK
DB09020
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID1022681
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
LACTMED
Bisacodyl
Created by admin on Fri Dec 15 15:14:58 GMT 2023 , Edited by admin on Fri Dec 15 15:14:58 GMT 2023
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC