Identification
- Summary
Docusate is a medication used to treat constipation associated with dry, hard stools, or opioid induced constipation.
- Brand Names
- Citranatal Harmony, Colace, Docusol, Docusol Plus, Dok, Dulcolax, Enemeez, Enemeez Plus, Ferralet 90, Laxacin, Pedia-lax Liquid, Peri-colace Reformulated Feb 2008, Promolaxin, Senexon S, Senokot-S
- Generic Name
- Docusate
- DrugBank Accession Number
- DB11089
- Background
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 7. Docusate can be orally or rectally administered. Docusate is on the World Health Organization's List of Essential Medicines10. 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 6,2,5. Recently there has been pressure to stop prescribing docusate as it has been identified as an ineffective medicine3,5,9. 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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Docusate (DB11089)
- Weight
- Average: 422.577
Monoisotopic: 422.23382426 - Chemical Formula
- C20H38O7S
- Synonyms
- Dioctyl sulfosuccinate
- Docusate hydrogen
- External IDs
- E480
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 efficacy3,5,9.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Constipation Combination Product in combination with: Sennosides (DB11365) ••• ••• •••••• Prevention of Constipation ••• ••• •••••••• •••••• ••••••• ••••••••• ••••••••••• ••••• Treatment of Constipation ••• ••• •••••••• •••••• ••••••• ••••••••• ••••••••••• ••••• Used in combination for symptomatic treatment of Occasional constipation Combination Product in combination with: Sorbitol (DB01638) ••• ••••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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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 7,4. Docusate's onset of action is 6-72 hours orally and 2-15 minutes rectally 7,8. 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
- Absorption
Docusate is not absorbed systemically7,9. As the actions of docusate are local and it is not absorbed, the pharmacokinetic parameters are not available9.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
If docusate is systemically absorbed, it undergoes biliary excretion 7,9.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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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.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The risk or severity of dehydration can be increased when Acetazolamide is combined with Docusate. Aclidinium The therapeutic efficacy of Docusate can be decreased when used in combination with Aclidinium. Alfentanil The therapeutic efficacy of Docusate can be decreased when used in combination with Alfentanil. Alloin The risk or severity of adverse effects can be increased when Docusate is combined with Alloin. Amantadine The therapeutic efficacy of Docusate can be decreased when used in combination with Amantadine. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Docusate calcium 6K7YS503HC 128-49-4 DWKPZOZZBLWFJX-UHFFFAOYSA-L Docusate potassium CIK9F54ZHR 7491-09-0 CACRHRQTJDKAPJ-UHFFFAOYSA-M Docusate sodium F05Q2T2JA0 577-11-7 APSBXTVYXVQYAB-UHFFFAOYSA-M - Active Moieties
Name Kind UNII CAS InChI Key Sodium cation ionic LYR4M0NH37 17341-25-2 FKNQFGJONOIPTF-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Audinorm / Clear ear / Colace / Correctol / Dialose / Docusol / Docusol 100 / Doxinate / Dulcoease / Rectalad enema / Surfak
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-docusate Sodium Capsule 100 mg Oral Angita Pharma Inc. 2021-06-14 Not applicable Canada 
Albert Docusate Capsule 240 mg Oral Aventis Pharma Ltd. 1991-12-31 2001-07-20 Canada Alta-docusate Sodium Capsule 100 mg Oral Altamed Pharma 2018-05-25 2023-07-01 Canada Apo-docusate Calcium Capsule 240 mg Oral Apotex Corporation 2002-11-25 Not applicable Canada Apo-docusate Sodium Capsule 100 mg Oral Apotex Corporation 2002-11-04 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 2 In 1laxative Stool Softener and Stiulant Laxative Docusate sodium (50 mg/1) + Sennosides (8.6 mg/1) Tablet, coated Oral Rite Aid 2020-06-01 Not applicable US 
2 In 1laxative Stool Softener and Stiulant Laxative Docusate sodium (50 mg/1) + Sennosides (8.6 mg/1) Tablet, coated Oral Rite Aid 2020-06-01 Not applicable US Acidobyl Docusate sodium (60 mg) + Dehydrocholic acid (120 mg) + Homatropine methylbromide (0.5 mg) + Sodium taurocholate (120 mg) Tablet Oral Desbergers LtÉe, Division Of Technilab Inc. 1951-12-31 1999-09-17 Canada Calcium Docuphen Cap Docusate calcium (60 mg / cap) + Phenolphthalein (65 mg / cap) Capsule Oral Pharmascience Inc 1988-12-31 1997-10-10 Canada CAREALL Senna-S Laxative Docusate sodium (50 mg/1) + Sennosides (8.6 mg/1) Tablet Oral New World Imports, Inc. 2016-04-18 2022-06-01 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BioFerr 90 Docusate 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 coated Oral Biocomp Pharma, Inc. 2014-07-01 Not applicable US CitraNatal 90 DHA Docusate 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) Tablet Oral Mission Pharmacal 2010-02-01 Not applicable US CitraNatal 90 DHA Docusate 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) Tablet Oral Mission Pharmacal Company 2014-04-11 Not applicable US CitraNatal Assure Docusate 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) Kit Oral Mission Pharmacal 2008-11-19 Not applicable US CitraNatal Assure Docusate 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) Capsule; Kit; Tablet, coated Oral Mission Pharmacal Company 2014-04-30 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acid esters
- Direct Parent
- Fatty acid esters
- Alternative Parents
- Dicarboxylic acids and derivatives / Sulfonyls / Organosulfonic acids / Alkanesulfonic acids / Carboxylic acid esters / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Alkanesulfonic acid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Fatty acid ester / Hydrocarbon derivative / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- alkanesulfonic acid, succinate ester (CHEBI:534)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- M7P27195AG
- CAS number
- 10041-19-7
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chapman RW, Sillery J, Fontana DD, Matthys C, Saunders DR: Effect of oral dioctyl sodium sulfosuccinate on intake-output studies of human small and large intestine. Gastroenterology. 1985 Sep;89(3):489-93. [Article]
- Docusate sodium/Senna: Drug Information [Link]
- Docusate sodium Drug Summary [Link]
- Alberta Health Services Drugs and Therapeutics Background- Stool Softeners: WHY Are They Still Used? [Link]
- World Health Organization List of Essential Medicines 2017 [Link]
- DailyMed: Docusate/Sennosides oral tablet [Link]
- External Links
- Human Metabolome Database
- HMDB0032386
- KEGG Drug
- D00305
- KEGG Compound
- C07874
- PubChem Substance
- 347911112
- ChemSpider
- 10862
- 82003
- ChEBI
- 534
- ChEMBL
- CHEMBL1477036
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Docusate
- MSDS
- Download (129 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Postoperative Bowel Movement / Postoperative Passage of Flatus 1 4 Completed Treatment Constipation 1 4 Completed Treatment Constipation / Ileus / Surgery 1 4 Terminated Prevention Analgesia / Constipation 1 4 Terminated Prevention Constipation 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule; kit; tablet, coated Oral Kit Oral Capsule Oral 50 mg/1 Solution Oral 10 mg / mL Liquid Rectal 100 mg/5mL Capsule Oral 100.0000 mg Syrup Oral 20 mg/5mL Capsule Oral 240 mg/1 Capsule Oral 100 mg/1 Capsule Oral 250 mg/1 Capsule, liquid filled Oral 100 mg/1 Capsule, liquid filled Oral 50 mg/1 Liquid Oral 100 mg/10mL Liquid Oral 50 mg/5mL Solution / drops Oral 10 mg / mL Capsule Oral 50 mg Syrup Oral 4 mg / mL Capsule, gelatin coated Oral 250 mg/1 Enema Rectal 283 mg / 5 mL Capsule Oral 240 mg / cap Capsule Oral 100 mg / cap Capsule, liquid filled Oral 200 mg Liquid Rectal 283 mg/5mL Liquid Rectal Tablet, film coated Oral 100 mg Tablet, coated Oral 50 mg Tablet Oral 100 mg / tab Capsule, liquid filled Oral 250 mg/250mg Capsule, liquid filled Oral 250 mg/1 Capsule, gelatin coated Oral 100 mg/601 Capsule, liquid filled; kit; tablet Oral Solution / drops Auricular (otic) Tablet, film coated Oral 100 mg/1 Tablet, coated Oral Tablet Oral Syrup Oral 50 mg / 5 mL Pill Tablet Oral 50 MG Solution Oral Solution Oral 0.400 g Tablet, chewable Buccal Capsule Oral Capsule Oral Liquid Oral 50 mg/15mL Capsule Oral 200 mg Syrup Oral 250 mg / 5 mL Capsule, gelatin coated; kit; tablet Oral Capsule, liquid filled Oral Capsule, gelatin coated Oral Tablet Oral 100 mg/1 Syrup Oral 20 mg / 5 mL Tablet, film coated Oral Pill Oral Liquid Oral 10 mg/1mL Syrup Oral 60 mg/15mL Solution Rectal Capsule, gelatin coated Oral 100 mg/1 Capsule, liquid filled Oral 200 mg/1 Capsule, liquid filled Oral 240 mg/1 Capsule, gelatin coated Oral 240 mg/1 Capsule Oral 240 mg Enema Rectal 283 mg/5mL Enema Rectal Capsule, liquid filled; kit Oral Liquid Auricular (otic) 5 mg/1ml Capsule Oral 250 mg Solution Auricular (otic) 5 mg/1ml Tablet Capsule Oral 100 mg Capsule - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 153-157 MSDS water solubility Soluble MSDS logP 3.95 MSDS - Predicted Properties
Property Value Source Water Solubility 0.00402 mg/mL ALOGPS logP 2.48 ALOGPS logP 5.24 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) -0.75 Chemaxon pKa (Strongest Basic) -6.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 106.97 Å2 Chemaxon Rotatable Bond Count 18 Chemaxon Refractivity 107.35 m3·mol-1 Chemaxon Polarizability 46.82 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00kf-8589000000-ed1a8e482c548d0d69cb Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0112900000-973751b930b5bac7e909 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00xs-0590300000-b8f700df9dc125124240 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-08fr-0923000000-99aefad90bb61e199a63 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0940000000-2a142098177751d38cb4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08i0-9600000000-dff93efacccdfa55deb0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fb9-0910000000-b8f5886c97ccca415bfb Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 222.2073638 predictedDarkChem Lite v0.1.0 [M-H]- 201.76112 predictedDeepCCS 1.0 (2019) [M+H]+ 219.4742638 predictedDarkChem Lite v0.1.0 [M+H]+ 204.11914 predictedDeepCCS 1.0 (2019) [M+Na]+ 222.1826638 predictedDarkChem Lite v0.1.0 [M+Na]+ 210.21228 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at April 18, 2024 09:15