Docusate

Identification

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Name
Docusate
Accession Number
DB11089
Type
Small Molecule
Groups
Approved
Description

Docusate, or dioctyl sulfosuccinate, is a stool softener indicated for the treatment of constipation1. Docusate acts by increasing the amount of water the stool absorbs in the gut, making the stool softer and easier to pass 6. Docusate can be orally or rectally administered. Docusate is on the World Health Organization's List of Essential Medicines9. However the effectiveness of docusate in treating constipation remains unclear, as several studies report docusate to be no more effective than placebo for increasing the frequency of stool or stool softening 2,5. Recently there has been pressure to stop prescribing docusate as it has been identified as an ineffective medicine3,5,8. Additionally, it does not appear to lessen symptoms associated with constipation such as abdominal cramps. Still docusate is available in over-the-counter products as a common laxative.

Structure
Thumb
Synonyms
  • Dioctyl sulfosuccinate
  • Docusate hydrogen
External IDs
E480
Product Ingredients
IngredientUNIICASInChI Key
Docusate calcium6K7YS503HC128-49-4DWKPZOZZBLWFJX-UHFFFAOYSA-L
Docusate potassiumCIK9F54ZHR7491-09-0CACRHRQTJDKAPJ-UHFFFAOYSA-M
Docusate sodiumF05Q2T2JA0577-11-7APSBXTVYXVQYAB-UHFFFAOYSA-M
Active Moieties
NameKindUNIICASInChI Key
Sodium cationionicLYR4M0NH3717341-25-2FKNQFGJONOIPTF-UHFFFAOYSA-N
Product Images
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Albert DocusateCapsuleOralAventis Pharma Ltd.1991-12-312001-07-20Canada
Alta-docusate SodiumCapsuleOralAltamed Pharma2018-05-25Not applicableCanada
Apo-docusate CalciumCapsuleOralApotex Corporation2002-11-25Not applicableCanada
Apo-docusate SodiumCapsuleOralApotex Corporation2002-11-04Not applicableCanada
Basic Care Stool SoftenerCapsule, liquid filled100 mg/1OralL. Perrigo Company2018-03-27Not applicableUs
Calax Cap 240mgCapsuleOralOdan Laboratories Ltd1989-12-312015-06-16Canada
ColaceCapsule50 mg/1OralAvrio Health L.P.1997-01-302016-08-31Us
ColaceSolution / drops10 mgOralBoyd Pharmaceuticals Inc.1997-04-01Not applicableCanada
ColaceCapsule, liquid filled50 mg/1OralAvrio Health L.P.1900-01-07Not applicableUs
ColaceCapsule50 mg/1OralCardinal Health2011-06-072013-12-31Us
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AcidobylDocusate sodium (60 mg) + Dehydrocholic acid (120 mg) + Homatropine methylbromide (0.5 mg) + Sodium taurocholate (120 mg)TabletOralDesbergers LtÉe, Division Of Technilab Inc.1951-12-311999-09-17Canada
Calcium Docuphen CapDocusate calcium (60 mg) + Phenolphthalein (65 mg)CapsuleOralPharmascience Inc1988-12-311997-10-10Canada
CAREALL Senna-S LaxativeDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)TabletOralNew World Imports, Inc.2016-04-18Not applicableUs
CitraNatal 90 DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (160 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (90 mg/1) + Nicotinamide (20 mg/1) + Potassium triiodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboprine (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2010-02-01Not applicableUs
CitraNatal DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (125 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (27 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2007-11-20Not applicableUs
ColaceDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, film coatedOralAvrio Health L.P.1957-02-08Not applicableUs
ColaceDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, film coatedOralAvrio Health L.P.1957-02-08Not applicableUs
Colistat PlusDocusate sodium (50 mg/1) + Sennosides (8.6 mg/1)Tablet, film coatedOralAmvilab Llc2015-07-16Not applicableUs
Correctol Laxative TabDocusate sodium (100 mg) + Phenolphthalein (65 mg)TabletOralSchering Plough Healthcare Products Canada, A Division Of Schering Canada Inc.1971-12-311997-08-08Canada
CVS Adult EnemaDocusate sodium (283 mg/4.6g) + Benzocaine (20 mg/4.6g)LiquidRectalSummit Pharmaceuticals2014-09-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BioFerr 90Docusate sodium (55 mg/1) + Ascorbic acid (138 mg/1) + Cyanocobalamin (16.8 ug/1) + Ferrous gluconate dihydrate (13.2 mg/1) + Folic acid (1.4 mg/1) + Iron (88.5 mg/1)Tablet, film coatedOralBiocomp Pharma, Inc.2014-07-01Not applicableUs
CitraNatal 90 DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (160 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (90 mg/1) + Nicotinamide (20 mg/1) + Potassium triiodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboprine (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2010-02-01Not applicableUs
CitraNatal 90 DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (159 mg/1) + Cupric oxide (2 mg/1) + Ferrous gluconate dihydrate (5 mg/1) + Folic acid (1 mg/1) + Iron (85 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Thiamine mononitrate (4.54 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal Company2014-04-11Not applicableUs
CitraNatal AssureDocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (124 mg/1) + Cholecalciferol (400 [iU]/1) + Copper (2 mg/1) + Doconexent (300 mg/1) + Folic acid (1 mg/1) + Icosapent (0.75 mg/1) + Iodine (150 ug/1) + Iron (35 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc (25 mg/1)KitOralMission Pharmacal Company2014-04-30Not applicableUs
CitraNatal AssureDocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (125 mg/1) + Cholecalciferol (400 [iU]/1) + Copper (2 mg/1) + Doconexent (300 mg/1) + Folic acid (1 mg/1) + Icosapent (0.75 mg/1) + Iodine (150 ug/1) + Iron (35 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc (25 mg/1)KitOralMission Pharmacal2008-11-19Not applicableUs
CitraNatal BloomDocusate sodium (55 mg/1) + Ascorbic acid (138 mg/1) + Cyanocobalamin (16.8 ug/1) + Ferrous gluconate dihydrate (13.2 mg/1) + Folic acid (1.4 mg/1) + Iron (88.5 mg/1)Tablet, film coatedOralMission Pharmacal Company2017-08-01Not applicableUs
CitraNatal BloomDocusate sodium (55 mg/1) + Ascorbic acid (138 mg/1) + Cyanocobalamin (16.8 ug/1) + Ferrous gluconate dihydrate (13.2 mg/1) + Folic acid (1.4 mg/1) + Iron (88.5 mg/1)Tablet, film coatedOralMission Pharmacal Company2017-08-012017-07-20Us
CitraNatal Bloom DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Crypthecodinium cohnii DHA oil (300 mg/300mg) + Cyanocobalamin (12 ug/1) + Ferrous gluconate dihydrate (1.5 mg/1) + Folic acid (1 mg/1) + Iron (88.5 mg/1)KitOralMission Pharmacal Company2018-01-18Not applicableUs
CitraNatal DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (125 mg/1) + Cupric oxide (2 mg/1) + Folic acid (1 mg/1) + Iron (27 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)TabletOralMission Pharmacal2007-11-20Not applicableUs
CitraNatal DHADocusate sodium (50 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (124 mg/1) + Cupric oxide (2 mg/1) + Doconexent (250 mg/1) + Folic acid (1 mg/1) + Icosapent (0.625 mg/1) + Iron (27 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)KitOralMission Pharmacal Company2014-05-22Not applicableUs
International/Other Brands
Audinorm / Clear ear / Colace / Correctol / Dialose / Docusol / Docusol 100 / Doxinate / Dulcoease / Rectalad enema / Surfak
Categories
UNII
M7P27195AG
CAS number
10041-19-7
Weight
Average: 422.577
Monoisotopic: 422.23382426
Chemical Formula
C20H38O7S
InChI Key
HNSDLXPSAYFUHK-UHFFFAOYSA-N
InChI
InChI=1S/C20H38O7S/c1-5-9-11-16(7-3)14-26-19(21)13-18(28(23,24)25)20(22)27-15-17(8-4)12-10-6-2/h16-18H,5-15H2,1-4H3,(H,23,24,25)
IUPAC Name
1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonic acid
SMILES
CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(O)(=O)=O

Pharmacology

Indication

Indicated for the treatment of constipation associated with dry, hard stools or opioid induced constipation4. Though recently, pressure has been building to end the use of docusate over concerns of efficacy3,5,8.

Associated Conditions
Pharmacodynamics

Docusate sodium is a laxative and an anionic detergent that supposedly promotes incorporation of water and fats into stool through a reduction in surface tension, resulting in softer fecal mass 6,4. Docusate's onset of action is 6-72 hours orally and 2-15 minutes rectally 6,7. The effects of docusate are thought to be exerted locally in the jejunum1.

Mechanism of action

Recent studies suggest that docusate's mechanism of action is due largely to it's surfactant effect in the intestines, which allow fat and water into the feces to soften the stool4.

Docusate’s mechanism of action was investigated in 1985 on healthy patients.1 Docusate was added directly to the jejunum based on calculated concentrations of docusate in the jejunum.1 At this concentration, there was an increase in secretion of water, sodium, chloride, and potassium as well as a decrease in absorption of glucose and bicarbonate1. Based on in vitro data, the authors suggested this effect was due to an increase in intracellular cyclic AMP either directly through docusate or E series prostaglandins.1

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Docusate is not absorbed systemically6,8. As the actions of docusate are local and it is not absorbed, the pharmacokinetic parameters are not available8.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

If docusate is systemically absorbed, it undergoes biliary excretion 6,8.

Half life
Not Available
Clearance
Not Available
Toxicity

Docusate is not known to be carcinogenic or cause reproductive toxicity. It was not mutagenic in the Ames assay MSDS. Acute oral LD50 in rat is 1900 mg/kg MSDS.

Affected organisms
  • Humans and other mammals
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 Docusate.
AclidiniumThe therapeutic efficacy of Docusate can be decreased when used in combination with Aclidinium.
AgmatineThe therapeutic efficacy of Docusate can be decreased when used in combination with Agmatine.
AlcuroniumThe therapeutic efficacy of Docusate can be decreased when used in combination with Alcuronium.
AlfentanilThe therapeutic efficacy of Docusate can be decreased when used in combination with Alfentanil.
AlloinThe risk or severity of adverse effects can be increased when Docusate is combined with Alloin.
AlphacetylmethadolThe therapeutic efficacy of Docusate can be decreased when used in combination with Alphacetylmethadol.
AlphaprodineThe therapeutic efficacy of Docusate can be decreased when used in combination with Alphaprodine.
AmantadineThe therapeutic efficacy of Docusate can be decreased when used in combination with Amantadine.
AmilorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Docusate.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

References

General References
  1. Moriarty KJ, Kelly MJ, Beetham R, Clark ML: Studies on the mechanism of action of dioctyl sodium sulphosuccinate in the human jejunum. Gut. 1985 Oct;26(10):1008-13. [PubMed:2414161]
  2. Tarumi Y, Wilson MP, Szafran O, Spooner GR: Randomized, double-blind, placebo-controlled trial of oral docusate in the management of constipation in hospice patients. J Pain Symptom Manage. 2013 Jan;45(1):2-13. doi: 10.1016/j.jpainsymman.2012.02.008. Epub 2012 Aug 11. [PubMed:22889861]
  3. MacMillan TE, Kamali R, Cavalcanti RB: Missed Opportunity to Deprescribe: Docusate for Constipation in Medical Inpatients. Am J Med. 2016 Sep;129(9):1001.e1-7. doi: 10.1016/j.amjmed.2016.04.008. Epub 2016 May 3. [PubMed:27154771]
  4. McRorie JW, Daggy BP, Morel JG, Diersing PS, Miner PB, Robinson M: Psyllium is superior to docusate sodium for treatment of chronic constipation. Aliment Pharmacol Ther. 1998 May;12(5):491-7. [PubMed:9663731]
  5. Hurdon V, Viola R, Schroder C: How useful is docusate in patients at risk for constipation? A systematic review of the evidence in the chronically ill. J Pain Symptom Manage. 2000 Feb;19(2):130-6. [PubMed:10699540]
  6. Docusate sodium/Senna: Drug Information [Link]
  7. Docusate sodium Drug Summary [Link]
  8. Alberta Health Services Drugs and Therapeutics Background- Stool Softeners: WHY Are They Still Used? [Link]
  9. World Health Organization List of Essential Medicines 2017 [Link]
External Links
Human Metabolome Database
HMDB0032386
KEGG Drug
D00305
KEGG Compound
C07874
PubChem Substance
347911112
ChemSpider
10862
ChEBI
534
ChEMBL
CHEMBL1477036
Drugs.com
Drugs.com Drug Page
Wikipedia
Docusate
AHFS Codes
  • 56:12.00 — Cathartics and Laxatives
MSDS
Download (129 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2RecruitingTreatmentDiabetic Gastroparesis1
2, 3CompletedTreatmentConstipation1
3CompletedTreatmentConstipation1
3RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD) / Dyspnea1
4CompletedTreatmentConstipation1
4CompletedTreatmentConstipation / General Surgery / Ileus1
4RecruitingPreventionConstipation2
4RecruitingPreventionPostoperative Bowel Movement / Postoperative Passage of Flatus1
4TerminatedPreventionAnalgesia / Constipation1
Not AvailableCompletedPreventionConstipation / Palliative Care1
Not AvailableCompletedPreventionFunctional Disorder of Intestine1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitOral
CapsuleOral50 mg/1
Solution / dropsOral
LiquidRectal100 mg/5mL
SyrupOral20 mg/5mL
CapsuleOral240 mg
CapsuleOral240 mg/1
CapsuleOral100 mg/1
CapsuleOral250 mg/1
Capsule, liquid filledOral100 mg/1
Capsule, liquid filledOral50 mg/1
LiquidOral100 mg/10mL
LiquidOral50 mg/5mL
Solution / dropsOral10 mg
SyrupOral20 mg
Tablet, film coatedOral100 mg/1
LiquidRectal283 mg/5mL
LiquidRectal
TabletOral
Capsule, liquid filledOral250 mg/1
Capsule, liquid filledOral250 mg/250mg
Capsule, gelatin coatedOral100 mg/601
Capsule, liquid filledOral
Tablet, coatedOral
TabletOral
CapsuleOral
LiquidOral50 mg/15mL
SyrupOral
Capsule, gelatin coatedOral
TabletOral100 mg/1
Tablet, film coatedOral
PillOral
LiquidOral10 mg/1mL
SyrupOral60 mg/15mL
CapsuleOral100 mg
Capsule, gelatin coatedOral100 mg/1
Capsule, liquid filledOral200 mg/1
Capsule, liquid filledOral240 mg/1
Capsule, gelatin coatedOral240 mg/1
CapsuleOral
EnemaRectal283 mg/5mL
EnemaRectal
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)153-157MSDS
water solubilitySolubleMSDS
logP3.95MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.00402 mg/mLALOGPS
logP2.48ALOGPS
logP5.24ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-0.75ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.97 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity107.35 m3·mol-1ChemAxon
Polarizability46.82 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Classification
Not classified

Drug created on December 03, 2015 09:51 / Updated on November 12, 2019 22:52