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Bisacodyl

HCID 2391
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
603-50-9
Standard SMILES
CC(=O)Oc1ccc(C(c2ccc(OC(C)=O)cc2)c2ccccn2)cc1
InChIKey
KHOITXIGCFIULA-UHFFFAOYSA-N
Molecular formula
C22H19NO4
Average molar mass
361.4 g/mol
Monoisotopic mass
361.13140809

Overview

Bisacodyl is a diarylmethane.

Names & identifiers

Preferred name
Bisacodyl
IUPAC
[4-[(4-acetyloxyphenyl)-pyridin-2-ylmethyl]phenyl] acetate
English name
Bisacodyl
Molecular formula
C22H19NO4
Molecular weight
361.39

Names & synonyms

bisacodyl603-50-9DulcolaxTheralaxSk-bisacodylBrocalaxDulcolanFenilaxanLaxansPyrilaxTeleminEndokolat
Show more names
bisacodil4,4’-(2-pyridylmethylene)-diphenolacetate(Pyridin-2-ylMethylene)bis(4,1-phenylene) diacetatelacoBicolLA96Aneolax
EulaxanGodalaxHillcolaxLaxadinLaxorexNigalaxStadalaxIvilax

Database identifiers

CAS
603-50-9
PubChem CID
2391
DTXSID
DTXSID1022681
ChEMBL
CHEMBL942
ChEBI
CHEBI:3125
UNII
10X0709Y6I
EC Number
210-044-4
Nikkaji
J3.307C

Properties

Computed structural properties

XLogP
3.8
Topological polar surface area
65.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
7
Heavy atoms
27
Formal charge
0
Complexity
457

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Pharmaceuticals -> Used in Switzerland

SpringerMaterials PropertiesFusion temperature
LogP · 2 items

log Kow = 3.37 /Estimated/

2.64

TasteTasteless
Color/Form · 2 items

WHITE TO OFF-WHITE CRYSTALLINE POWDER IN WHICH PARTICLES HAVING LONGEST DIAMETER SMALLER THAN 50 MICRONS PREDOMINATE

Crystals

Solubility · 3 items

Practically insoluble in water and alkaline solvents. Soluble in acids, alcohol, acetone, propylene glycol and other organic solvents.

1 G SOL IN 210 ML ALCOHOL, 2.5 ML CHLOROFORM, 275 ML ETHER

>54.2 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 4 items

Breast Feeding; Lactation; Cathartics; Gastrointestinal Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Laxatives

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (10.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 59 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Other Safety InformationIMAP assessments - Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate (ester): Environment tier I assessment
FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl bisacodyl, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Hazard Classes and CategoriesAcute Tox. 4 (10.2%)

Safety & protection

Storage ConditionsBisacodyl rectal suppositories and enteric-coated tablets should be stored at les than 30 °C.
Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Chemistry & industry

Pharmacology

ATC Code · 5 items

A06AB02

A - Alimentary tract and metabolism

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Pharmacodynamics · 1 item

Patients should be counselled regarding abdominal pain, nausea, vomiting, or a change in bowel function that lasts longer than 2 weeks. It has a wide therapeutic index, as patients can take 5-15 mg orally. Patients taking bisacodyl should be counselled before taking the medication if they are already experiencing abdominal pain, nausea, vomiting, or a change in bowel function lasting longer than 2 weeks. Patients should also be counselled to stop taking the medication if they experience rectal bleeding or no bowel movement in 12 hours.

Mechanism of Action · 6 items

Bisacodyl is deacetylated to the active bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM) by an intestinal deacetylase. BHPM can stimulate parasympathetic nerves in the colon directly to increase motility and secretions. Bisacodyl stimulates adenylate cyclase, increasing cyclic AMP, leading to active transport of chloride and bicarbonate out of cells. Sodium ions, potassium ions, and water passively leave the cell; while sodium and chloride ions are unable to be reabsorbed. Water is also be transported from the luminal side of cells into the vasculature by aquaporin 3. Bisacodyl decreases expression of aquaporin 3, preventing water from moving into the vasculature, which may contribute to increased water in the colon. Bisacodyl directly stimulates parasympathetic nerves in the colon, stimulating contraction of longitudinal smooth muscle but not circular smooth muscle.

Bisacodyl is a stimulant laxative, ... acting directly on the colonic mucosa-where it stimulates sensory nerve endings to produce parasympathetic reflexes resulting in increased peristaltic contractions of the colon. The contact action of the drug is restricted to the colon, and motility of the small intestine is not appreciably influenced.

/Bisacodyl/ increases water retention in the stool by coating surfaces of stool and intestines with a water-immisicible film. Lubricant effect eases passage of contents through intestines. Emulsification of lubricant tends to enhance its ability to soften stool mass. /Laxatives/

Recent studies show that these drugs alter fluid and electrolyte absorption producing net intestinal fluid accumulation and laxation. Some of these drugs may directly stimulate active intestinal ion secretion. Increased concentrations of cyclic 3',5'-adenosine monophosphate (cAMP), occurring in colonic mucosa cells following administration of stimulant laxatives, may alter the permeability of these cells and mediate active ion secretion thereby producing net fluid accumulation and laxative action. /Stimulant Laxatives/

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides/.
Melting Point138 °C
Vapor Pressure4.8X10-8 mm Hg at 25 °C /Estimated/
Henry's Law ConstantHenry's Law constant = 7.3X10-12 atm-cu m/mole at 25 °C /Estimated/
Collision Cross Section · 2 items

173.45 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

193.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
138 °C · 138°C
Boiling point
493.21 °C · 493.21°C (rough estimate)
Density
1.2545 · 1.2545 (rough estimate)
refractive index
1.5614 · 1.5614 (estimate)
storage temp.
2 · Sealed in dry,2-8°C
solubility
Practically insoluble in water, soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute mineral acids.
pka
4.69 · 4.69±0.10(Predicted)
form
Solid
color
White to Off-White
Water Solubility
Soluble in alcohol (slightly), ether (slightly), chloroform, and acetone. Insoluble in water.
λmax
220 nm · 220nm(MeOH)(lit.)
Merck
14 · 14,1242
Henry's Law Constant
1.4 · 1.4×106 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Stable. Incompatible with strong oxidizing agents.
Major Application
forensics and toxicologypharmaceutical (small molecule)veterinary
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
InChIKey
KHOITXIGCFIULA-UHFFFAOYSA-N
SMILES
CC(=O)Oc1ccc(cc1)C(c2ccc(OC(C)=O)cc2)c3ccccn3
LogP
3.453 · 3.453 (est)
CAS DataBase Reference
603 · 603-50-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
10 X0709Y6I · 10X0709Y6I
NCI Drug Dictionary
bisacodyl
ATC code
6 AB02,A06AB52,A06AG02 · A06AB02,A06AB52,A06AG02
NIST Chemistry Reference
Bisacodyl(603-50-9)
EPA Substance Registry System
4 · Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate (ester) (603-50-9)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Protein binding
Negligible
Excreted unchanged in urine
30 % · 30%
Volume of distribution
See 'Other information'.(L/kg)
Biological half-life
See 'Other information'.
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
22 · 22-36/37/38
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
8750000 · SM8750000
TSCA
TSCA listed
HS Code
2933399090 · 2933399090
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data
603 · 603-50-9(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: >3 g/kg (Schmidt)
Preventive Measures · 2 items

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

Toxicology

Interactions · 4 items

Milk, antacids, and histamine H2-receptor antagonist such as cimetidine, famotidine, nizatidine or ranitidine may cause the enteric coating to dissolve too rapidly, resulting in gastric or duodenal irritation when administered within one hour of bisacodyl tablets.

Chronic use or over use of laxatives may reduce serum potassium concentrations by by promoting excessive potassium loss from the intestinal tract; may interfer with potassium-retaining effects of potassium sparing diuretics.

In rat colon in situ bisacodyl stimulated biosynthesis of prostaglandin E (PGE). Inhibition of prostaglandin biosynthesis by pretreatment with indomethacin decreased effect of diphenolic laxatives.

Bisacodyl inhibited gastric emptying & motility in rats by activating reflex arising from small intestine. This effect was not prevented by alpha- or beta-sympatholytic, or by parasympatholytic agents. It was antagonized by quinine & quinidine, as well as by chloroquine & mepacrine. Inhibition of gastric motility by cathartics does not appear to be due to an effect on adrenergic or cholinergic pathways but rather involves a purinergic mechanism.

HepatotoxicityBisacodyl has not been associated with serum enzyme elevations during therapy or with instances of clinically apparent liver injury.
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 85,000(SRC), determined from a structure estimation method(2), indicates that bisacodyl is expected to be immobile in soil(SRC). Volatilization of bisacodyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.3X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Bisacodyl is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-8 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 85,000(SRC), determined from a structure estimation method(2), indicates that bisacodyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.3X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A base-catalyzed second-order hydrolysis rate constant of 2.3 L/mole-sec(SRC) was estimated using a structure estimation method(5); this corresponds to half-lives of 35 and 3.5 days at pH values of 7 and 8, respectively(5). According to a classification scheme(6), an estimated BCF of 78(SRC), from an estimated log Kow of 3.37(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bisacodyl, which has an estimated vapor pressure of 4.8X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bisacodyl may be removed from the air by wet and dry deposition(SRC). Bisacodyl does not absorb light at wavelengths >290 nm(3) and would not be expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse Effects · 1 item

The most common adverse effects, seen in more than 5% of patients taking bisacodyl, are diarrhea, abdominal pain (mainly in the upper abdomen), and headache. Although it is unlikely that chronic use of bisacodyl is harmful to the colon, it could induce abdominal discomfort and cramping pain. Joo JS et al summarized that 45% of patients using bisacodyl or other laxatives (phenolphthalein, senna, and casanthranol) more than 3 times per week for 1 year or longer had subsequent radiographic changes of colonic redundancy and dilation of the colon, with loss of haustral markings which did not occur in the control groups. These agents may cause a neuronal injury or damage colonic longitudinal musculature.

Toxicity SummarySigns and Symptoms of Overdose
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for bisacodyl can be estimated to be 85,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that bisacodyl is expected to be immobile in soil.

Human Toxicity Excerpts · 1 item

/SIGNS AND SYMPTOMS/ With long term use or overdosage of stimulant laxatives, electrolyte disturbances including hypokalemia, hypocalcemia, metabolic acidosis or alkalosis, abdominal pain, diarrhea, malabsorption, weight loss , and protein-losing enteropathy may occur Electrolyte disturbances may produce vomiting and muscle weakness; rarely osteomalacia, secondary aldosteronism, and tetany may occur. Pathologic changes in including structural damage to the myenteric plexus, severe and permanent interference with colonic motility, and hypertrophy of the muscularis mucosae may occur with chronic use. /Stimulant laxatives/

Artificial Pollution SourcesBisacodyl's production and use as a laxative(1) may result in its release to the environment through various waste streams(SRC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Bisacodyl

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Environmental Bioconcentration · 1 item

An estimated BCF of 78 was calculated for bisacodyl(SRC), using an estimated log Kow of 3.37(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not altered physically or chemically once released into the environment(SRP).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for bisacodyl is estimated as 7.3X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bisacodyl is expected to be essentially nonvolatile from water surfaces(2). Bisacodyl's Henry's Law constant indicates that volatilization from moist soil surfaces should not occur(SRC). Bisacodyl is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 1 item

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Dietary supplementation with bisacodyl at concentrations ranging from 1 to 0.3% was found to induce both calculi and epithelial proliferation lesions, including a transitional-cell carcinoma, in the urinary bladder of F344uCrj rats. In order to clarify the relationship between the bisacodyl-associated urinary bladder calculi and the development of proliferative lesions in the urinary bladder, male and female rats were administered bisacodyl-diets at concentrations of 0.3, 0.1, and 0.03% for 32 wk. Both sexes of animals treated with bisacodyl suffered from diarrhea throughout the experimental period. Epithelial proliferative lesions and calculus formation were observed only in the urinary bladder of male rats given the 0.3% bisacodyl diet. Proliferative lesions and increases of bromouracil deoxyriboside (BUdR) labeling indices were found only in the urinary bladder epithelium of rats with calculi, the severity of the former correlating with the calculus weight ...

Regulatory information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl bisacodyl, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
SM8750000
hs_code
2933399090
Toxicity
LD50 orally in rats: >3 g/kg (Schmidt)
risk_code
22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H315-H319-H335
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazardous Substances Data
603-50-9(Hazardous Substances Data)

Bisacodyl caused dose-dependent contractions in isolated guinea pig ileum & taenia coli which was not prevented by atropine or pheniramine. It prevented acetylcholine- & histamine-induced contractions. Bisacodyl-induced contractions were not caused by a decrease in endogenous cyclic amp level. However, both endogenous cyclic amp & verapamil (a calcium transport inhibitor) inhibited bisacodyl-induced contractions, suggesting site of action on calcium-dependent contractile system of smooth muscle cells.

Intestinal secretagogues as well as the laxative, bisacodyl, raise the K+ efflux rate across the mucosal border by 200-300%. Results suggest that laxatives may increase rate of K+ secretion into the colonic lumen by raising the K+ permeability of the mucosal border.

Biological Half-LifeData regarding the half life of bisacodyl is not readily available. The half life of the active metabolite, BHPM, in lactating women was 7.3 h after a single 10 mg oral dose and 10.0 h after multiple doses.
Metabolism/Metabolites · 3 items

Bisacodyl is deacetylated to the active bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM) by an intestinal deacetylase. A small amount of BHPM is absorbed from the gastrointestinal tract, and is glucuronidated before elimination.

Following oral or rectal administration bisacodyl is converted to the active desacetyl metabolite bis(p-hydroxyphenyl)pyridyl-2-methane by intestinal and bacterial enzymes.

HPLC method which permits simultaneous detection of bisacodyl (BIS) & its monodesacetylated (mono) as well as totally desacetylated (DES) form, was used to study the intestinal handling of BIS (20 nmol/mL), when incubated for 60 min at the mucosal side of the preparations specified. In jejunal mucosa fluid, BIS disappeared completely in short time, & there was nearly equivalent rise in DES; mono was transitorily present. Hydrolysis was also rapid in mucosal fluid which had been in contact with jejunal sacs for 30 sec, but BIS was stable in blank incubations. Hydrolysis of BIS was slower by colonic than by jejunal sacs, & all 3 forms were present during incubation. It seemed still lower in mucosal fluid which had been in contact with colonic sac for 5 min. BIS & DES accumulate in jejunal & colonic serosal fluid mainly as conjugates (above 95%), & DES was in all cases the only conjugated metabolite present. Accumulation in jejunal serosal fluid was same whether BIS or DES was added.

FDA Pharmacological Classification · 6 items

10X0709Y6I

BISACODYL

Physiologic Effects [PE] - Increased Large Intestinal Motility

Established Pharmacologic Class [EPC] - Stimulant Laxative

Physiologic Effects [PE] - Stimulation Large Intestine Fluid/Electrolyte Secretion

Bisacodyl is a Stimulant Laxative. The physiologic effect of bisacodyl is by means of Increased Large Intestinal Motility and Stimulation Large Intestine Fluid/Electrolyte Secretion.

MeSH Pharmacological Classification · 3 items

Agents that are used to stimulate evacuation of the bowels.

Agents that produce a soft formed stool, and relax and loosen the bowels, typically used over a protracted period, to relieve CONSTIPATION.

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Absorption, Distribution and Excretion · 6 items

Oral formulations of bisacodyl are only 16% bioavailable. A 10 mg enteric coated oral tablet reaches a Cmax of 26 ng/mL with a Tmax of 8 hours, while a 10 mg oral solution reaches a Cmax of 237 ng/mL with a Tmax of 1.7 hours. A 10 mg suppository reaches a Cmax of 0-64 ng/mL. In lactating women, 10mg of oral bisacodyl reaches a Cmax of 20.5-195 ng/mL, with a Tmax of 3-4 hours, and a geometric mean AUC after a single dose of 471 h\*ng/mL. After multiple doses, the geometric mean AUC decreases to 311 h\*ng/mL.

The majority of bisacodyl is eliminated in the feces. 13.8-17.0% of a bisacodyl dose is eliminated in the urine as the active metabolite BHPM.

Data regarding the volume of distribution of bisacodyl is not readily available. However, the volume of distribution of the active metabolite, BHPM, in lactating women is 181 L after a single dose and 289 L at steady state.

Data regarding the clearance of bisacodyl is not readily available. The apparent plasma clearance of the active metabolite, BHPM, in lactating women after a single 10 mg oral dose is 272 mL/min and after multiple doses is 412 mL/min.

Absorption of bisacodyl ... is minimal following oral or rectal administration. Any bisacodyl that is absorbed is metabolized in the liver and excreted in the urine and/or distributed in milk.

Following oral administration of therapeutic dosages of diphenylmethane derivatives, /bowel/ evacuation is produced in 6 to 8 hours. Rectally administered bisacodyl ... produces evacuation of the colon in within 15 minutes to 1 hour.

Uses & manufacturing

Uses · 3 items

Cathartic

MEDICATION

Use (kg; approx.) in Germany (2009): >1000

U.S. Exports · 2 items

(1977) No Data

(1979) No Data

U.S. Imports · 2 items

(1978) 1.01X10+6 G (PRINCPL CUSTMS DISTS)

(1979) 1.94X10+6 G (PRINCPL CUSTMS DISTS)

U.S. Production · 2 items

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1978) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Consumption PatternsESSENTIALLY 100% AS A CATHARTIC
Methods of Manufacturing · 3 items

Condensation of 2-pyridinecarboxaldehyde with phenol in the presence of sulfuric acid, followed by esterification with acetic anhydride and anhydrous sodium acetate

... Produced by condensation of 2-pyridinealdehyde with phenol in the presence of dehydrating compounds. Subsequently, the phenolic hydroxyl groups are acetylated.

Preparation: GB 730243; A. Kottler, E. Seeger, US 2764590 (1955,1956 both to Thomae).

Formulations/Preparations · 5 items

Complex with tannin: Bisacodyl tannex; Clysodrast.

Bisacodyl is available in an enteric-coated preparation given once daily, the usual oral dose for which is 10 to 15 mg for adults and 5 to 10 mg for children 6 to 12 years old.

Bisacodyl Enema is supplied in a 1.25 fluid ounce (37 mL) ready-to-use squeeze bottle.

/Bisacodyl/ stimulant laxative tablets are supplied in cartons of 25 tablets (5 mg each tablet) wrapped in a foil seal.

Bisacodyl suppositories are supplied in cartons of 4 individually foil-wrapped suppositories.

Household ProductsInformation on 2 consumer products that contain Bisacodyl in the following categories is provided:
General Manufacturing Information · 2 items

Phenol, 4,4'-(2-pyridinylmethylene)bis-, 1,1'-diacetate: ACTIVE

Information available in 2005 indicated that Bisacodyl was used in the manufacture of pharmaceutical preparations in the following countries: Algeria, Antigua & Barbuda, Argentina, Aruba, Australia, Austria, Bahamas, Bahrain, Bangladesh, Barbados, Belgium, Bermuda, Brazil, Bulgaria, Canada, Cayman Islands, Chile, Colombia, Croatia, Cyprus, Czech Republic, Denmark, Ecuador, Egypt, Finland, France, Germany, Greece, Grenada, Guyana, Haiti, Hong Kong, Hungary, India, Indonesia, Ireland, Iraq, Israel, Italy, Jamaica, Japan, Jordan, Kenya, Kuwait, Lebanon, Libyan Arab Jamahiriya, Luxembourg, Malaysia, Malta, Mauritius, Mexico, Morocco, Netherlands, Netherlands Antilles, New Zealand, Nigeria, Norway, Oman, Poland, Portugal, Qatar, Romania, Russian Federation, Saint Lucia, Saint Vincent & The Grenadines, Saudi Arabia, Singapore, Slovenia, South Africa, Spain, Sweden, Switzerland, Sudan, Syrian Arab Republic, Thailand, Trinidad & Tobago, Tunisia, Turkey, United Arab Emirates, United Kingdom, United States, Yemen, Yugoslavia (1,2)

Applications · 3 items

UsesCathartic.

UsesStimulant laxative.

UsesBisacodyl is used in the inhibition of (Na+K)ATPase, the increase of mucosal PGE2, and the activation of adenyl cyclase in rat intestine studies. It is used as a laxative drug. It is typically prescribed for relief of constipation.

Upstream & downstream products

Upstream raw materials

2-PicolinePhenolAcetic anhydridePHENYL 2‐PYRIDINECARBOXYLATEp,p'-(2-pyridylmethylene)bisphenol4-(Hydroxy(pyridin-2-yl)methyl)phenolp-hydroxyphenyl 2-pyridyl ketone4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENYLBORONIC ACID2-PYRIDINECARBOXYLICACID CHLORIDE2-Pyridinecarboxaldehyde

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
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Additional notes

DefinitionChEBI: Bisacodyl is a diarylmethane.