Bisacodyl

Identification

Summary

Bisacodyl is a stimulant laxative used for the temporary relief of occasional constipation and cleansing of the colon as a preparation for colonoscopy in adults.

Brand Names
Alophen Reformulated Jan 2008, Bi-peglyte, Bisac-evac, Carters Little Pills, Dulcolax, Fleet Mineral Oil, Gavilyte-H and Bisacodyl
Generic Name
Bisacodyl
DrugBank Accession Number
DB09020
Background

Bisacodyl, a diphenylmethane derivative, is a commonly used over the counter stimulant laxative for occasional constipation.5,9 Both bisacodyl and picosulfate are metabolized to the same active metabolite bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM).4,5,6

Bisacodyl was patented on 25 September 19568 but has been used as a laxative since 1952.5

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 361.3906
Monoisotopic: 361.131408101
Chemical Formula
C22H19NO4
Synonyms
  • Bisacodilo
  • Bisacodyl
  • Bisacodyle
  • Bisacodylum
  • Phenol, 4,4'-(2-pyridinylmethylene)bis-, diacetate (ester)
External IDs
  • LA 96 a
  • LA96a

Pharmacology

Indication

Bisacodyl is indicated to relieve occasional constipation and irregularity.9

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Patients should be counselled regarding abdominal pain, nausea, vomiting, or a change in bowel function that lasts longer than 2 weeks.9 It has a wide therapeutic index, as patients can take 5-15 mg orally.9 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.9 Patients should also be counselled to stop taking the medication if they experience rectal bleeding or no bowel movement in 12 hours.9

Mechanism of action

Bisacodyl is deacetylated to the active bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM) by an intestinal deacetylase.4,5,6 BHPM can stimulate parasympathetic nerves in the colon directly to increase motility and secretions.5

Bisacodyl stimulates adenylate cyclase, increasing cyclic AMP, leading to active transport of chloride and bicarbonate out of cells.5 Sodium ions, potassium ions, and water passively leave the cell; while sodium and chloride ions are unable to be reabsorbed.5

Water is also be transported from the luminal side of cells into the vasculature by aquaporin 3.7 Bisacodyl decreases expression of aquaporin 3, preventing water from moving into the vasculature, which may contribute to increased water in the colon.7

Bisacodyl directly stimulates parasympathetic nerves in the colon, stimulating contraction of longitudinal smooth muscle but not circular smooth muscle.3,5

TargetActionsOrganism
UAquaporin-3
negative modulator
Humans
USodium/Potassium Transporting ATPase subunits
inhibitor
Humans
Absorption

Oral formulations of bisacodyl are only 16% bioavailable.2,3 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.10 A 10 mg suppository reaches a Cmax of 0-64 ng/mL.10

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.6 After multiple doses, the geometric mean AUC decreases to 311 h*ng/mL.6

Volume of distribution

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.6

Protein binding

Not Available

Metabolism

Bisacodyl is deacetylated to the active bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM) by an intestinal deacetylase.4,5,6 A small amount of BHPM is absorbed from the gastrointestinal tract, and is glucuronidated before elimination.6

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Route of elimination

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.6

Half-life

Data 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.6

Clearance

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.6

Adverse Effects
Adverseeffects
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Toxicity

Patients experiencing an overdose of bisacodyl may present with more severe diarrhea and electrolyte imbalance.1 Patients should be treated with symptomatic and supportive measures.

The oral LD50 in rats is 4320 mg/kg, and in mice is 17500 mg/kg.10

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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.
AlfentanilThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Alfentanil.
AlloinThe risk or severity of adverse effects can be increased when Bisacodyl is combined with Alloin.
AlmasilateThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Almasilate.
AluminiumThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aluminium.
Aluminium phosphateThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aluminium phosphate.
Aluminum hydroxideThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Aluminum hydroxide.
AmantadineThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Amantadine.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Bisacodyl.
Interactions
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Food Interactions
  • Avoid milk and dairy products. Take at least 1 hour before or after antacids and milk.
  • Take separate from antacids. Take at least 1 hour before or after antacids and milk.

Products

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Active Moieties
NameKindUNIICASInChI Key
DeacetylbisacodylunknownR09078E41Y603-41-8LJROKJGQSPMTKB-UHFFFAOYSA-N
Product Images
International/Other Brands
Bisalax (Actavis) / Bolax (Unifarma) / Boots Constipation Relief (Boots) / Derderance (Nisshin Seiyaku) / Dulco-Lax (Boehringer Ingelheim) / Dulcolaxo (Boehringer Ingelheim) / Fleet Laxative (Baxter) / Florisan (Boehringer Ingelheim) / Laxitab (Ranbaxy) / Reliable Gentle Laxative Tablets (Teva) / Spirolax / Verecolene C.M. (GlaxoSmithKline)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BisacodylTablet5 mg/1OralRemedy Repack2010-08-042012-07-01US flag
Magic Bullet Laxative SuppositorySuppository10 mgRectalSmordins Dispensary Ltd.Not applicableNot applicableCanada flag
Soflax EX Micro-enemaEnema; Suspension2 mg / mLRectalPharmascience IncNot applicableNot applicableCanada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-bisacodyl ECTablet5 mgOralAngita Pharma Inc.Not applicableNot applicableCanada flag
AlophenTablet, coated5 mg/1OralNumark Brands, Inc1907-04-15Not applicableUS flag
Alophen TabletsTablet, delayed release5 mg / tabOralNumark Laboratories, Inc.1998-08-312009-07-31Canada flag
Apo-bisacodylTablet, delayed release5 mgOralApotex Corporation1982-12-31Not applicableCanada flag
Apo-bisacodyl Sup 10mgSuppository10 mg / supRectalApotex Corporation1988-12-31Not applicableCanada flag
APO-BISACODYL TABLET 5 mgTablet, coated5 mgOralPHARMAFORTE SINGAPORE PTE LTD1988-12-28Not applicable
Avedana Gentle LaxativeSuppository10 mg/1RectalUnipack, Inc.2017-09-17Not applicableUS flag
BEACOLUX TABLET 5MG ENTERIC COATEDTablet, delayed releaseOralDUOPHARMA MANUFACTURING (BANGI) SDN BHD2020-09-08Not applicableMalaysia flag
Becolax TabletsTablet, delayed release5 mgOralViva Pharmaceutical Inc.Not applicableNot applicableCanada flag
Best Choice Bisacodyl LaxativeTablet, coated5 mg/1OralBest Choice (Valu Merchandisers Company)2012-11-022023-12-29US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BEKUNIS 3 MG/5 MG KAPLI TABLET, 30 ADETBisacodyl (3 mg) + Sennosides (5 mg)Tablet, film coatedOralABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Bekunis DrageesBisacodyl (5 mg) + Sennosides (60 mg) + Sennosides (20 mg) + Sennosides (25 mg)TabletOralRoha Arzneimittel Gmbh1974-12-312009-07-02Canada flag
Bi-peglyteBisacodyl (5 mg / tab) + Polyethylene glycol (59.55 g / sachet) + Potassium chloride (0.76 g / sachet) + Sodium bicarbonate (1.69 g / sachet) + Sodium chloride (1.46 g / sachet) + Sodium sulfate (5.74 g / sachet)Kit; Powder, for solution; Tablet, delayed releaseOralPendopharm Division Of Pharmascience Inc2010-06-06Not applicableCanada flag
Bicholate LilasBisacodyl (5 mg) + Aloe vera leaf (12 mg) + Frangula purshiana bark (30 mg) + Sodium taurocholate (60 mg)TabletOralSabex Inc1998-10-282009-11-24Canada flag
CHINTA-LAXBisacodyl (5 mg) + Docusate sodium (15 mg)TabletOralWELLMEX SDN BHD2020-09-082020-12-18Malaysia flag
DulcolaxBisacodyl (5 mg/1) + Bisacodyl (10 mg/1)KitOral; RectalBoehringer Ingelheim2003-04-012014-08-31US flag
DulcolaxBisacodyl (5 mg/1) + Bisacodyl (10 mg/1)KitOral; RectalBoehringer Ingelheim2003-04-012014-08-31US flag
Dyrax-Q TabBisacodyl (5 mg/161mg) + Docusate sodium (16.75 mg/161mg)TabletOralCho-A Pharm.Co.,Ltd.2019-10-25Not applicableUS flag
GaviLyte-H and BisacodylBisacodyl (5 mg/1) + Polyethylene glycol (210 g/2L) + Potassium chloride (0.74 g/2L) + Sodium bicarbonate (2.86 g/2L) + Sodium chloride (5.6 g/2L)KitOralLupin Pharmaceuticals, Inc.2015-04-21Not applicableUS flag
Gentlax SBisacodyl (5 mg) + Docusate sodium (50 mg)TabletOralPurdue Pharma2004-10-122011-08-04Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BisacodylBisacodyl (5 mg/1)TabletOralRemedy Repack2010-08-042012-07-01US flag
BisacodylBisacodyl (5 mg/1)TabletOralCardinal Health2011-06-022011-10-31US flag
BisacodylBisacodyl (10 mg/1)SuppositoryRectalPhysicians Total Care, Inc.2003-09-042013-01-15US flag
PCP 100 KitBisacodyl (5 mg/1) + Magnesium citrate (1.745 g/29.6mL) + Metoclopramide hydrochloride (10 mg/1) + Petrolatum (0.76 g/1g) + Polyethylene glycol (17 g/17g)KitOralAsclemed Usa, Inc.2014-01-02Not applicableUS flag

Categories

ATC Codes
A06AB52 — Bisacodyl, combinationsA06AB02 — BisacodylA06AG02 — Bisacodyl
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Diphenylmethane / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
10X0709Y6I
CAS number
603-50-9
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

References

Synthesis Reference

U.S. Patent 2,764,590.

General References
  1. 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. [Article]
  2. Roth W, Beschke K: [Pharmacokinetics and laxative effect of bisacodyl following administration of various dosage forms]. Arzneimittelforschung. 1988 Apr;38(4):570-4. [Article]
  3. Manabe N, Cremonini F, Camilleri M, Sandborn WJ, Burton DD: Effects of bisacodyl on ascending colon emptying and overall colonic transit in healthy volunteers. Aliment Pharmacol Ther. 2009 Nov 1;30(9):930-6. doi: 10.1111/j.1365-2036.2009.04118.x. Epub 2009 Aug 12. [Article]
  4. Krueger D, Demir IE, Ceyhan GO, Zeller F, Schemann M: bis-(p-hydroxyphenyl)-pyridyl-2-methane (BHPM)-the active metabolite of the laxatives bisacodyl and sodium picosulfate-enhances contractility and secretion in human intestine in vitro. Neurogastroenterol Motil. 2018 Jul;30(7):e13311. doi: 10.1111/nmo.13311. Epub 2018 Feb 14. [Article]
  5. Lawrensia S, Raja A: Bisacodyl . [Article]
  6. Friedrich C, Richter E, Trommeshauser D, de Kruif S, van Iersel T, Mandel K, Gessner U: Absence of excretion of the active moiety of bisacodyl and sodium picosulfate into human breast milk: an open-label, parallel-group, multiple-dose study in healthy lactating women. Drug Metab Pharmacokinet. 2011;26(5):458-64. doi: 10.2133/dmpk.dmpk-11-rg-007. Epub 2011 Jun 21. [Article]
  7. Ikarashi N, Baba K, Ushiki T, Kon R, Mimura A, Toda T, Ishii M, Ochiai W, Sugiyama K: The laxative effect of bisacodyl is attributable to decreased aquaporin-3 expression in the colon induced by increased PGE2 secretion from macrophages. Am J Physiol Gastrointest Liver Physiol. 2011 Nov;301(5):G887-95. doi: 10.1152/ajpgi.00286.2011. Epub 2011 Aug 25. [Article]
  8. US Patent: US2764590 [Link]
  9. DailyMed:Bet-R-Prep (Bisacodyl) Oral Tablet [Link]
  10. FDA Pharmacology Review: HalfLytely (Polyethylene Glycol-3350, Sodium Chloride, Sodium Bicarbonate, Potassium Chloride) Oral Solution and Bisacodyl Oral Tablet [Link]
KEGG Drug
D00245
PubChem Compound
2391
PubChem Substance
310264977
ChemSpider
2299
BindingDB
61400
RxNav
1596
ChEBI
3125
ChEMBL
CHEMBL942
ZINC
ZINC000003830321
Drugs.com
Drugs.com Drug Page
Wikipedia
Bisacodyl
FDA label
Download (62.7 KB)
MSDS
Download (495 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableBowel preparation therapy1
4CompletedNot AvailableColonoscopy1
4CompletedDiagnosticBowel Cleansing Quality1
4CompletedOtherChronic Constipation1
4CompletedPreventionChronic Obstructive Pulmonary Disease (COPD)1
4CompletedPreventionThoracoabdominal Aortic Aneurysms1
4CompletedSupportive CareColonic Motility Index / Constipation1
4CompletedTreatmentColon Cleansing1
4CompletedTreatmentColonoscopy6
4CompletedTreatmentColonoscopy Preparation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
TabletTopical5 mg/1
Kit; powder, for solution; tablet, delayed releaseOral
Tablet, delayed releaseOral5 m
SuppositoryRectal0.01 g/2g
TabletOral
Tablet, delayed releaseOral5 mg/1
SuppositoryRectal10 mg/1
SuppositoryRectal5.0 mg
Tablet, delayed releaseOral5 mg / tab
TabletOral5.0 mg
Tablet, coatedOral5 mg
SuppositoryRectal10 mg
SuppositoryRectal5 mg
KitOral; Rectal
Tablet, coatedOral5 mg/1
Tablet, delayed release; tablet, film coatedOral
Tablet, coatedOral
SuppositoryRectal
SuspensionRectal10 mg / 5 mL
SuppositoryRectal0.01 g
Tablet, coatedOral5.0000 mg
TabletOral
PillOral5 mg/5mg
TabletOral5 mg/5mg
EnemaRectal10 mg/30mL
KitOral
Tablet
SuppositoryRectal10 mg / sup
Tablet, film coatedOral5 mg
TabletOral5 mg
SuppositoryRectal10 mg/2000mg
Tablet, delayed releaseOral
Enema; suspensionRectal2 mg / mL
SuppositoryRectal10 MG/G
TabletOral5 mg/1
Capsule, gelatin coatedOral5 mg/1
Tablet, film coatedOral5 mg/1
Tablet, sugar coatedOral5 mg/1
Tablet, coatedOral
Tablet, sugar coatedOral5 mg
Tablet, coatedOral10 mg
Tablet, delayed releaseOral5 mg
Capsule
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US2764590No1953-03-161973-03-16US flag
US7291324No2007-11-062022-10-22US flag

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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Negative modulator
General Function
Water channel required to promote glycerol permeability and water transport across cell membranes. Acts as a glycerol transporter in skin and plays an important role in regulating SC (stratum corneum) and epidermal glycerol content. Involved in skin hydration, wound healing, and tumorigenesis. Provides kidney medullary collecting duct with high permeability to water, thereby permitting water to move in the direction of an osmotic gradient. Slightly permeable to urea and may function as a water and urea exit mechanism in antidiuresis in collecting duct cells. It may play an important role in gastrointestinal tract water transport and in glycerol metabolism (By similarity).
Specific Function
Glycerol channel activity
Gene Name
AQP3
Uniprot ID
Q92482
Uniprot Name
Aquaporin-3
Molecular Weight
31543.605 Da
References
  1. Ikarashi N, Baba K, Ushiki T, Kon R, Mimura A, Toda T, Ishii M, Ochiai W, Sugiyama K: The laxative effect of bisacodyl is attributable to decreased aquaporin-3 expression in the colon induced by increased PGE2 secretion from macrophages. Am J Physiol Gastrointest Liver Physiol. 2011 Nov;301(5):G887-95. doi: 10.1152/ajpgi.00286.2011. Epub 2011 Aug 25. [Article]
  2. Rachmilewitz D, Karmeli F, Okon E: Effects of bisacodyl on cAMP and prostaglandin E2 contents, (Na + K) ATPase, adenyl cyclase, and phosphodiesterase activities of rat intestine. Dig Dis Sci. 1980 Aug;25(8):602-8. doi: 10.1007/BF01318874. [Article]
  3. Schreiner J, Nell G, Loeschke K: Effect of diphenolic laxatives on Na+-K+-activated ATPase and cyclic nucleotide content of rat colon mucosa in vivo. Naunyn Schmiedebergs Arch Pharmacol. 1980 Sep;313(3):249-55. doi: 10.1007/BF00505741. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hormone binding
Specific Function
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates th...

Components:
References
  1. Schreiner J, Nell G, Loeschke K: Effect of diphenolic laxatives on Na+-K+-activated ATPase and cyclic nucleotide content of rat colon mucosa in vivo. Naunyn Schmiedebergs Arch Pharmacol. 1980 Sep;313(3):249-55. doi: 10.1007/BF00505741. [Article]

Drug created on June 24, 2014 17:03 / Updated on October 20, 2021 19:48