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

Description

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.

Originator

Approval Year

1958
115
Targets

Targets

Primary TargetPharmacologyConditionPotency
Interacts
314
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Withdrawn
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
Comparison of three forms of bowel preparations for screening flexible sigmoidoscopy.
2001 Jul-Aug
[Treatment of idiopathic constipation].
2001 Sep
[Laxative effect of poly(ethylene oxide) 1500 per se and in combination with bisacodyl].
2001 Sep-Oct
MR colonography: status and perspective.
2002 Jul-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
Effects of a meal and bisacodyl on colonic motility in healthy volunteers and patients with slow-transit constipation.
2003 Jul
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
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
Bisacodyl rectal preparation can decrease infectious complications of transrectal ultrasound-guided prostate biopsy.
2003 Sep
Current treatment options for chronic constipation.
2004
Melanosis coli?
2004 Jan 8
[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
Polyethylene glycol versus sodium phosphate in bowel cleansing for colonoscopy: a randomized trial.
2005 Jun
[Nausea, vomiting and constipation in palliative care].
2006 Feb 23
The bowel cleansing for colonoscopy. A randomized trial comparing three methods.
2006 Mar-Apr
Factitious diarrhea induced by stimulant laxatives: accuracy of diagnosis by a clinical reference laboratory using thin layer chromatography.
2007 Jan
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
Bowel preparation versus no preparation before ileal urinary diversion.
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
Association of potentially inappropriate medication use with adverse outcomes in ambulatory elderly patients with chronic diseases: experience in a Taiwanese medical setting.
2008
CT colonography with limited bowel preparation: performance characteristics in an increased-risk population.
2008 Apr
Comparison of two column characterisation systems based on pharmaceutical applications.
2008 May 2
Patents

Patents

JP4653399B2
50
JPH0987186A
2

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
In Vitro Use Guide
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 16 16:36:26 UTC 2022
Edited
by admin
on Fri Dec 16 16:36:26 UTC 2022
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 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
WHO-ATC A06AG02
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
WHO-ATC A06AB02
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
NDF-RT N0000009871
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
WHO-VATC QA06AB52
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
WHO-VATC QA06AB02
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
WHO-ATC A06AB52
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
NCI_THESAURUS C29697
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
LIVERTOX NBK548124
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
WHO-ATC A06AB20
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
NDF-RT N0000009371
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
NDF-RT N0000175812
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL942
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
MERCK INDEX
M2516
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY Merck Index
RS_ITEM_NUM
1074007
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
INN
824
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
CAS
603-50-9
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
ECHA (EC/EINECS)
210-044-4
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
PUBCHEM
2391
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
DAILYMED
10X0709Y6I
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
MESH
D001726
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
RXCUI
1596
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY RxNorm
WIKIPEDIA
BISACODYL
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
EVMPD
SUB05846MIG
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
DRUG CENTRAL
375
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
NCI_THESAURUS
C28870
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
NSC
755914
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
FDA UNII
10X0709Y6I
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
HSDB
3016
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
DRUG BANK
DB09020
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
EPA CompTox
DTXSID1022681
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
LACTMED
Bisacodyl
Created by admin on Fri Dec 16 16:36:27 UTC 2022 , Edited by admin on Fri Dec 16 16:36:27 UTC 2022
PRIMARY
Related Record Type Details
Structure of DEACETYLBISACODYL
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of BISACODYL
IMPURITY -> PARENT
ASSAY (TITRATION)
USP
Structure of 2,4'-(PYRIDIN-2-YLMETHYLENE)DIPHENYL DIACETATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2,4'-(2-PYRIDYLMETHYLENE)DIPHENOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2,4'-(2-PYRIDYLMETHYLENE)DIPHENOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2,4'-(PYRIDIN-2-YLMETHYLENE)DIPHENYL DIACETATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MONOACETYL BISACODYL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DEACETYLBISACODYL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of MONOACETYL BISACODYL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DEACETYLBISACODYL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966