PRODUCTS

DOCUSATE

Docusate may also be used for purposes not listed in this medication guide.
Docusate is often used to relieve constipation and irregularity and is available in a variety of forms, including capsules, tablets, and liquids.
Docusate is mainly used to treat constipation, but it may be used to prevent constipation for people who are taking opioid medicines.

CAS Number: 10041-19-7
as salt: 577-11-7
EC Number: 204-093-1
E number: E480 (thickeners, ...)
Molecular Formula: C20H37O7S

SYNONYMS:
Dioctyl sulfosuccinate, Sodium 1,4-bis(2-ethylhexyl) sulfosuccinate, Bis(2-ethylhexyl) sodium sulfosuccinate, dioctyl sodium sulfosuccinate, DSS, sodium dioctyl sulfosuccinate, sulfo-butanedioic acid 1,4-bis(2-ethylhexyl) ester, sodium salt sulfosuccinic acid 1,4-bis(2-ethylhexyl) ester sodium salt, DOCUSATE, Docusate hydrogen, 10041-19-7, Spolion 8, DIOCTYL SULFOSUCCINATE, Dioctyl sulfosuccinic acid, 1,4-Bis(2-ethylhexyl) 2-sulphosuccinate, 1,4-Bis(2-ethylhexyl) sulfosuccinate, Diocto, EINECS 233-124-0, Doc-Q-Lace, Dioctylsulfosuccinsaeure, 1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonic acid, CHEBI:534, Butanedioic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester, UNII-M7P27195AG, M7P27195AG, 1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonic acid, Bis(2-ethylhexyl)succinat-2-sulfonsaeure, Di-beta-ethylhexyl sodium sulfo-succinate, 1,4-Bis(2-ethylhexyloxy)-1,4-dioxo-2-butansulfonsaeure, Butanedionic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester, Butanedioic acid, 2-sulfo-, 1,4-bis(2-ethylhexyl) ester, 1,4-Bis((2-ethylhexyl)oxy)-1,4-dioxobutane-2-sulfonic acid, 1,4-Bis(2-ethylhexyloxy)-1,4-dioxo-2-butansulfonsaeure [IUPAC], C20H38O7S, DIOCTYL DISODIUM SULFOSUCCINATE, DIOCTYLSULFOSUCCINATE, Docusates, Dionex, Sulfosuccinic Acid bis(2-Ethylhexyl) Ester, DOCUSATE [VANDF], bmse000720, D0X4FM, DOCUSATE [WHO-DD], DOCUSATES [MART.], SCHEMBL41958, CHEMBL1477036, DTXSID1044279, bis(2-ethylhexyl) sulfosuccinate, C20-H38-O7-S, LMFA07010721, Sulfosuccinic acid bis(2-ethylhexyl), DB11089, LS-186430, C07874, EN300-20176424, Q27105309, Succinic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester, 21954-86-9, 1,4-Bis((2-ethylhexyl)oxy)-1,4-dioxobutane-2-sulfonic acid, Butanedioic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester, Butanedioic acid, 2-sulfo-, 1,4-bis(2-ethylhexyl) ester, Succinic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester (USP)

Docusate is a stool softener used to treat occasional constipation and hard stools.
Docusate is the common chemical and pharmaceutical name of the anion bis(2-ethylhexyl) sulfosuccinate, also commonly called dioctyl sulfosuccinate (DOSS).
Salts of this anion, especially docusate sodium, are widely used in medicine as laxatives and as stool softeners, by mouth or rectally.

Some studies claim that docusate is not more effective than a placebo for improving constipation.
Other docusate salts with medical use include those of calcium and potassium.
Docusate salts are also used as food additives, emulsifiers, dispersants, and wetting agents, among other uses.

It is on the World Health Organization's List of Essential Medicines.
In 2022, Docusate was the 148th most commonly prescribed medication in the United States, with more than 3 million prescriptions.
In 2022, the combination with senna was the 261st most commonly prescribed medication in the United States, with more than 1 million prescriptions.

Docusate, or dioctyl sulfosuccinate, is a stool softener indicated for the treatment of constipation.
Docusate acts by increasing the amount of water the stool absorbs in the gut, making the stool softer and easier to pass.
Docusate can be orally or rectally administered.

Docusate is on the World Health Organization's List of Essential Medicines.
Docusate prevents and treats occasional constipation.
Docusate works by softening the stool, making it easier to have a bowel movement.

Docusate belongs to a group of medications called laxatives.
Docusate is a stool softener that makes bowel movements softer and easier to pass.
Docusate is a stool softener.

Docusate works by increasing the amount of water the stool absorbs in the gut, making the stool softer and easier to pass.
Docusate is a stool softener that makes bowel movements softer and easier to pass.
It's a combination of 2 medicines, docusate, in a single tablet.

Docusate increases the amount of fluid in your stools (poo) to soften them and make them easier to pass.
Docusate stimulates the muscles in your gut to help move your stools along so they can be passed more easily.
Docusate is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 tonnes per annum.

USES and APPLICATIONS of DOCUSATE:
Docusate may also be used to empty bowels before surgery or other medical procedures.
Docusate works by increasing the water content of stools.
Other medical uses of Docusate: Docusate sodium, when used with ear syringing, may help with earwax removal, particularly in the case of impaction.

Docusate is also used as a lubricant in the production of tablets and as an emulsifier in topical preparations and other suspensions.
Docusate is used stool softener in pharmaceutical formulations
Docusate is used emulsifying agent in cosmetics and industrial products

Docusate is used surfactant for cleaning and wetting purposes
Docusate is used dispersing agent in food and agricultural applications
Docusate is used as a surfactant in a wide range of applications, often under the name Aerosol-OT.

Docusate is unusual in that it can form microemulsions without the use of co-surfactants, and it has a rich variety of aqueous-phase behavior including multiple liquid crystalline phases.
Microencapsulation: Docusate is the most widely used surfactant in reverse micelle encapsulation studies.

Docusate may be used for other purposes; ask your health care provider or pharmacist if you have questions.
Docusate is used to treat occasional constipation.
Some medications and conditions can make constipation more likely.

Stool softeners such as docusate are often the first method used for preventing and treating this type of constipation.
Docusate is often used when straining to have a bowel movement should be avoided (such as after a heart attack or surgery).
Docusate is a stool softener.

Docusate works by increasing the amount of water the stool absorbs in the gut, making the stool softer and easier to pass.
Relief is usually seen in 1 to 3 days with this medication.
Docusate is used to relieve occasional constipation (irregularity).

Docusate is a medication used to treat constipation associated with dry, hard stools, or opioid induced constipation.
Docusate may also be used for purposes not listed in this medication guide.

Docusate is often used to relieve constipation and irregularity and is available in a variety of forms, including capsules, tablets, and liquids.
Docusate is mainly used to treat constipation, but it may be used to prevent constipation for people who are taking opioid medicines.

Docusate is used in the following products: coating products, fillers, putties, plasters, modelling clay, washing & cleaning products, adhesives and sealants, finger paints and fertilisers.
Other release to the environment of Docusate is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Other release to the environment of Docusate is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials), outdoor use in long-life materials with high release rate (e.g. tyres, treated wooden products, treated textile and fabric, brake pads in trucks or cars, sanding of buildings (bridges, facades) or vehicles (ships)), indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment) and indoor use in long-life materials with high release rate (e.g. release from fabrics, textiles during washing, removal of indoor paints).

Release to the environment of Docusate can occur from industrial use: of articles where the substances are not intended to be released and where the conditions of use do not promote release.
Docusate can be found in products with material based on: fabrics, textiles and apparel (e.g. clothing, mattress, curtains or carpets, textile toys), plastic (e.g. food packaging and storage, toys, mobile phones), wood (e.g. floors, furniture, toys) and leather (e.g. gloves, shoes, purses, furniture).

Docusate is used in the following products: washing & cleaning products and polishes and waxes.
Docusate is used in the following areas: mining, agriculture, forestry and fishing, formulation of mixtures and/or re-packaging and municipal supply (e.g. electricity, steam, gas, water) and sewage treatment.

Docusate is used for the manufacture of: chemicals, textile, leather or fur, plastic products and food products.
Other release to the environment of Docusate is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.

Docusate is used in the following products: metal working fluids, polymers, lubricants and greases, hydraulic fluids, plant protection products, pH regulators and water treatment products and textile treatment products and dyes.
Docusate has an industrial use resulting in manufacture of another substance (use of intermediates).

Release to the environment of Docusate can occur from industrial use: formulation of mixtures, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, as processing aid, for thermoplastic manufacture and formulation in materials.

Docusate is used in the following products: polymers, washing & cleaning products, textile treatment products and dyes, lubricants and greases, pH regulators and water treatment products, metal working fluids, leather treatment products and hydraulic fluids.
Docusate is used in the following areas: mining, agriculture, forestry and fishing, municipal supply (e.g. electricity, steam, gas, water) and sewage treatment and formulation of mixtures and/or re-packaging.

Docusate is used for the manufacture of: chemicals, textile, leather or fur, plastic products and food products.
Release to the environment of Docusate can occur from industrial use: in processing aids at industrial sites, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, formulation of mixtures and manufacturing of the substance.

Release to the environment of Docusate can occur from industrial use: manufacturing of the substance, formulation of mixtures, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid and for thermoplastic manufacture.

-Food additive uses of Docusate:
Docusate has been approved by the US FDA as a "generally recognized as safe" (GRAS) additive.
Docusate is used in a variety of food products, as a surface active agent, stabilizer, thickener, wetting agent, processing aid, solubilizing agent, emulsifier, and dispersant.

The highest amount of Docusate found in food products is 0.5% by weight, which include pasteurized cheese spreads, cream cheeses and salad dressings.
The FDA also approved Docusate's use as a wetting agent or solubilizer for flavoring agents in carbonated and non-carbonated drinks at levels up to 10 parts per million.

-Constipation uses of Docusate:
The main medical use of docusate sodium is to treat constipation, acting as a laxative and stool softener.
In painful anorectal conditions such as hemorrhoid and anal fissures, Docusate can help avoid pain caused by straining during bowel movements.

When administered by mouth, a bowel movement often occurs in 1 to 3 days, while rectal use may be effective within 20 minutes.
Sodium docusate is recommended as a stool softener for children.
However, Docusate's effectiveness for constipation is poorly supported by evidence.

Multiple studies have found docusate to be no more effective than a placebo for improving constipation.
Others have found Docusate to be less useful for the treatment of chronic constipation than psyllium.
The medication may be given to people who are receiving opioid medication, although prolonged use may cause irritation of the gastrointestinal tract.

SYNTHESIS OF DOCUSATE:
Docusate can be obtained by treating dioctyl maleate with sodium bisulfite. The bisulfite anion adds to the double bond:
−CH=CH− + HSO−3 → −CH(−SO−3)−CH2−

HISTORY OF DOCUSATE:
Sodium docusate was patented in 1937 by Coleman R. Caryl and Alphons O. Jaeger for American Cyanamid, which commercialized it for many years as a detergent under the brand name Aerosol OT.

Docusate's use for the treatment of constipation was first proposed in 1955 by James L. Wilson and David G. Dickinson, and quickly popularized under the name Doxinate.

MECHANISM OF ACTION OF DOCUSATE:
Docusate is an anionic surfactant, which works by reducing the surface tension of the stool, allowing more intestinal water and fat to combine with the stool.
This decreases the strain and discomfort associated with constipation.

Docusate does not stay in the gastrointestinal tract but is absorbed into the bloodstream and excreted via the gallbladder after undergoing extensive metabolism.

The effect of docusate may not necessarily be all due to its surfactant properties.
Perfusion studies suggest that docusate inhibits fluid absorption or stimulates secretion in the portion of the small intestine known as the jejunum.

CHEMISTRY OF DOCUSATE:
Structure and properties
The structural formula of the docusate anion is R−O−C(=O)−CH(SO−3)−CH2−C(=O)−O−R, where R is the 2-ethylhexyl group H3C−(CH2)3−C(−CH2−CH3)H−CH2−.
The conjugate acid can be described as the twofold carboxylate ester of sulfosuccinic acid with 2-ethylhexanol.

Docusate is a white, wax-like, plastic solid, with an odor suggestive of octyl alcohol.
Docusate starts to decompose at about 220 °C.
The solubility of Docusate in water is 14 g/L at 25 °C, increasing to 55 g/L at 70 °C.

Solubility of Docusate is better in less polar solvents: 1:30 in ethanol, 1:1 in chloroform and diethylether, and practically unlimited in petroleum ether (25 °C).
Docusate also is highly soluble in glycerol, although this is a rather polar solvent.

Docusate is also highly soluble in xylene, oleic acid, acetone, diacetone alcohol, methanol, isopropanol, 2-butanol, methyl acetate, ethyl acetate, furfurol, and vegetable oils.
The ester groups are easily cleaved under basic conditions, but are stable against acids.

HOW DOES DOCUSATE WORK?
Increases the amount of water absorbed by the stool in the intestine
Makes stool softer and easier to pass

WHAT IS DOCUSATE AND HOW DOES DOCUSATE WORK?
Docusate is used to treat occasional constipation.
Some medications and conditions can make constipation more likely.

PHYSICAL and CHEMICAL PROPERTIES of DOCUSATE:
Appearance: White to off-white waxy solid or powder
Molecular Formula: C20H37NaO7S
Molecular Weight: 444.56 g/mol
Melting Point: 153–157°C
Boiling Point: Decomposes before boiling
Solubility: Soluble in water, alcohols, and organic solvents
Density: ~1.1 g/cm³
pH: 5.5–7.5 (in aqueous solution)
Surface Tension Reduction: Excellent, promotes emulsification
Physical state: Wax like

Color: white
Odor: No data available
Melting point/freezing point:
Melting point/range: 173 - 179 °C
Initial boiling point and boiling range: > 200 °C at 984 hPa
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: No data available
Flash point: No data available
Autoignition temperature: > 180 °C - Relative self-ignition temperature for solids

Decomposition temperature: No data available
pH: No data available
Viscosity
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water solubility 8,17 g/l at 20 °C soluble
Partition coefficient: n-octanol/water: No data available
Vapor pressure: No data available
Density: 1,146 g/cm3 at 27,4 °C
Relative density: No data available
Relative vapor density: No data available

Particle characteristics: No data available
Explosive properties: No data available
Oxidizing properties: The product has been shown not to be oxidizing.
Surface tension: 30,65 mN/m at 1g/l at 20 °C
Molecular Weight: 422.6 g/mol
XLogP3-AA: 5.1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 7
Rotatable Bond Count: 18
Exact Mass: 422.23382472 g/mol
Monoisotopic Mass: 422.23382472 g/mol

Topological Polar Surface Area: 115Å²
Heavy Atom Count: 28
Formal Charge: 0
Complexity: 539
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 3
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Molecular form: C20H38O7S
Appearance: NA

Mol. Weight: 422.58
Storage: 2-8°C Refrigerator
Formula: C20H37O7S
Molar mass: 421.57 g·mol−1
3D model (JSmol): Interactive image
As salt: Interactive image
Density: 1.1 g/cm3
Melting point: 153 to 157 °C (307 to 315 °F), 173-179 °C
Solubility in water: 1 in 70 parts mg/mL (20 °C)
Chemical Formula: C20H37NaO7S
InChI Key: APSBXTVYXVQYAB-UHFFFAOYSA-M
InChI: InChI=1S/C20H38O7S.Na/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);/q;+1/p-1
IUPAC Name: sodium 1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonate
SMILES: [Na+].CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S([O-])(=O)=O

FIRST AID MEASURES of DOCUSATE:
-Description of first-aid measures:
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Immediately call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed:
No data available

ACCIDENTAL RELEASE MEASURES of DOCUSATE:
-Personal precautions, protective equipment and emergency procedures:
*Advice for non-emergency personnel:
Ensure adequate ventilation.
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up with suitable equipment.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of DOCUSATE:
-Extinguishing media:
*Suitable extinguishing media:
Water
Foam
Carbon dioxide (CO2)
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Suppress (knock down) gases/vapors/mists with a water spray jet.
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of DOCUSATE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Tightly fitting safety goggles
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter type ABEK-P
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of DOCUSATE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of DOCUSATE:
-Reactivity:
No data available
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .
-Possibility of hazardous reactions:
No data available
-Conditions to avoid:
no information available