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Details

Stereochemistry ACHIRAL
Molecular Formula C22H19NO4
Molecular Weight 361.3914
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BISACODYL

SMILES

CC(=O)Oc1ccc(cc1)C(c2ccc(cc2)OC(=O)C)c3ccccn3

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 361.3914
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

1.08414717E12
PubMed

PubMed

TitleDatePubMed
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
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
Management of constipation in residents with dementia: sorbitol effectiveness and cost.
2004 Jul-Aug
A prospective randomized trial comparing low-dose oral sodium phosphate plus stimulant laxatives with large volume polyethylene glycol solution for colon cleansing.
2004 Nov
Day-to-day variations during clinical drug monitoring of morphine, morphine-3-glucuronide and morphine-6-glucuronide serum concentrations in cancer patients. A prospective observational study.
2004 Oct 4
Bowel preparation of outpatients for intravenous urography: efficacy of castor oil versus bisacodyl.
2005 Apr
[Therapeutic options of chronic constipation].
2005 Dec
[Constipation: Initial evaluation and diagnostic approach].
2005 Jul-Sep
Polyethylene glycol versus sodium phosphate in bowel cleansing for colonoscopy: a randomized trial.
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
Alterations in the colonic flora and intestinal permeability and evidence of immune activation in chronic constipation.
2005 Nov
Capsule endoscopy for gastrointestinal bleeding with an obscure etiology.
2005 Sep
Colonic ischemia with laxative use in young adults.
2005 Sep
Colonic manometry as predictor of cecostomy success in children with defecation disorders.
2006 Apr
Phenolphthalein and bisacodyl: assessment of genotoxic and carcinogenic responses in heterozygous p53 (+/-) mice and syrian hamster embryo (SHE) assay.
2006 Apr
Optimizing use of opiates in the management of cancer pain.
2006 Dec
A prospective study comparing oral sodium phosphate solution to a bowel cleansing preparation with nutrition food package in children.
2006 Feb
Development and application of an automated solution stability assay for drug discovery.
2006 Feb
[Nausea, vomiting and constipation in palliative care].
2006 Feb 23
Pharmacologic management of constipation in the critically ill patient.
2006 Jul
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
Which is the optimal bowel preparation for colonoscopy - a meta-analysis.
2006 May
Efficacy and safety of bisacodyl in the acute treatment of constipation: a double-blind, randomized, placebo-controlled study.
2006 May 15
Commonly used preparations for colonoscopy: efficacy, tolerability, and safety--a Canadian Association of Gastroenterology position paper.
2006 Nov
Comparison of bisacodyl and sodium picosulphate in the treatment of chronic constipation.
2007 Apr
Factitious diarrhea induced by stimulant laxatives: accuracy of diagnosis by a clinical reference laboratory using thin layer chromatography.
2007 Jan
Development and validation of three stability-indicating methods for determination of bisacodyl in pure form and pharmaceutical preparations.
2007 Jan-Feb
Randomized controlled trial of bisacodyl suppository versus placebo for postoperative ileus after elective colectomy for colon cancer.
2007 Jul
Fundamental elements for successful performance of CT colonography (virtual colonoscopy).
2007 Jul-Aug
[Constipation in patients with diabetes mellitus].
2007 Nov 1
Clinical trial: sodium phosphate tablets are preferred and better tolerated by patients compared to polyethylene glycol solution plus bisacodyl tablets for bowel preparation.
2007 Nov 15
Bowel preparation versus no preparation before ileal urinary diversion.
2007 Oct
Purple urine bag syndrome in geriatric wards: two faces of a coin?
2007 Oct
A randomized, multicenter study comparing the safety and efficacy of sodium phosphate tablets with 2L polyethylene glycol solution plus bisacodyl tablets for colon cleansing.
2007 Oct
Clinical trial: an efficacy evaluation of reduced bisacodyl given as part of a polyethylene glycol electrolyte solution preparation prior to colonoscopy.
2007 Oct 15
[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
CT colonography: optimisation, diagnostic performance and patient acceptability of reduced-laxative regimens using barium-based faecal tagging.
2008 Jan
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
Influence of thoracic epidural analgesia on postoperative pain relief and ileus after laparoscopic colorectal resection : Benefit with epidural analgesia.
2009 Feb
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 Jun 25 21:02:11 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:11 UTC 2021
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
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
BISACODYL [WHO-DD]
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 Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
WHO-ATC A06AG02
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
WHO-ATC A06AB02
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
NDF-RT N0000009871
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
WHO-VATC QA06AB52
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
WHO-VATC QA06AB02
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
WHO-ATC A06AB52
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
NCI_THESAURUS C29697
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
LIVERTOX 109
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
WHO-ATC A06AB20
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
NDF-RT N0000009371
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
NDF-RT N0000175812
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL942
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
MERCK INDEX
M2516
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY Merck Index
INN
824
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
CAS
603-50-9
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
210-044-4
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
PUBCHEM
2391
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
MESH
D001726
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
RXCUI
1596
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
BISACODYL
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
EVMPD
SUB05846MIG
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
USP_CATALOG
1074007
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
375
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
NCI_THESAURUS
C28870
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
FDA UNII
10X0709Y6I
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
HSDB
3016
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
DRUG BANK
DB09020
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
EPA CompTox
603-50-9
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
LACTMED
Bisacodyl
Created by admin on Fri Jun 25 21:02:11 UTC 2021 , Edited by admin on Fri Jun 25 21:02:11 UTC 2021
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
IMPURITY -> PARENT
ASSAY (TITRATION)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC