Docusate is the common chemical and pharmaceutical name of the

anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...

bis(2-ethylhexyl) sulfosuccinate, also commonly called dioctyl sulfosuccinate (DOSS). It is on the

World Health Organization's List of Essential Medicines The WHO Model List of Essential Medicines (aka Essential Medicines List or EML), published by the World Health Organization (WHO), contains the medications considered to be most effective and safe to meet the most important needs in a health s ...

Salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively ...

of this anion, especially docusate sodium, are widely used in

medicine Medicine is the science and Praxis (process), practice of caring for a patient, managing the diagnosis, prognosis, Preventive medicine, prevention, therapy, treatment, Palliative care, palliation of their injury or disease, and Health promotion ...

laxative Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lub ...

s and as

stool softeners Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...

, by mouth or rectally. In 2020, it was the 163rd most commonly prescribed medication in the United States, with more than 3million prescriptions. Some studies claim that docusate is not more effective than a

placebo A placebo ( ) is a substance or treatment which is designed to have no therapeutic value. Common placebos include inert tablets (like sugar pills), inert injections (like Saline (medicine), saline), sham surgery, and other procedures. In general ...

for improving constipation. Other docusate salts with medical use include those of

calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar t ...

and

potassium Potassium is the chemical element with the symbol K (from Neo-Latin '' kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosp ...

. Docusate salts are also used as

food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (sal ...

emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althoug ...

dispersant A dispersant or a dispersing agent is a substance, typically a surfactant, that is added to a suspension of solid or liquid particles in a liquid (such as a colloid or emulsion) to improve the separation of the particles and to prevent their set ...

s, and wetting agents, among other uses.

History

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 A detergent is a surfactant or a mixture of surfactants with cleansing properties when in dilute solutions. There are a large variety of detergents, a common family being the alkylbenzene sulfonates, which are soap-like compounds that are m ...

under the brand name Aerosol OT. Its 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.

Medical use

Constipation

The main medical use of docusate sodium is to treat

constipation Constipation is a bowel dysfunction that makes bowel movements infrequent or hard to pass. The stool is often hard and dry. Other symptoms may include abdominal pain, bloating, and feeling as if one has not completely passed the bowel moveme ...

, acting as a laxative and stool softener. In painful

anorectal Anorectal anomalies are congenital malformations of the anus and rectum. One anal anomaly, imperforate anus has an estimated incidence of 1 in 5000 births.MedLine Plus.Imperforate anus" Retrieved 13 July 2005. It affects boys and girls with simi ...

conditions such as

hemorrhoid Hemorrhoids (or haemorrhoids), also known as piles, are vascular structures in the anal canal. In their normal state, they are cushions that help with stool control. They become a disease when swollen or inflamed; the unqualified term '' ...

and

anal fissure An anal fissure is a break or tear in the skin of the anal canal. Anal fissures may be noticed by bright red anal bleeding on toilet paper and undergarments, or sometimes in the toilet. If acute they are painful after defecation, but with chroni ...

s, it 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, its effectiveness for constipation is poorly supported by evidence. Multiple studies have found docusate to be no more effective than a

for improving constipation. Others have found it to be less useful for the treatment of chronic constipation than

psyllium Psyllium , or ispaghula , is the common name used for several members of the plant genus '' Plantago'' whose seeds are used commercially for the production of mucilage. Psyllium is mainly used as a dietary fiber to relieve symptoms of both consti ...

. The medication may be given to people who are receiving

opioid Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioi ...

medication, although prolonged use may cause irritation of the gastrointestinal tract.

Other medical uses

Docusate sodium, when used with ear syringing, may help with

earwax Earwax, also known by the medical term cerumen, is a brown, orange, red, yellowish or gray waxy substance secreted in the ear canal of humans and other mammals. It protects the skin of the human ear canal, assists in cleaning and lubrication, ...

removal, particularly in the case of impaction. Sodium docusate is also used as a

lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...

in the production of tablets and as an

in topical preparations and other suspensions.

Precautions and contraindications

Docusate sodium is approved and recommended as safe during

pregnancy Pregnancy is the time during which one or more offspring develops ( gestates) inside a woman's uterus (womb). A multiple pregnancy involves more than one offspring, such as with twins. Pregnancy usually occurs by sexual intercourse, but ...

and

breastfeeding Breastfeeding, or nursing, is the process by which human breast milk is fed to a child. Breast milk may be from the breast, or may be expressed by hand or pumped and fed to the infant. The World Health Organization (WHO) recommends that bre ...

. Docusate is not recommended in people with

appendicitis Appendicitis is inflammation of the appendix. Symptoms commonly include right lower abdominal pain, nausea, vomiting, and decreased appetite. However, approximately 40% of people do not have these typical symptoms. Severe complications of a r ...

acute abdomen An acute abdomen refers to a sudden, severe abdominal pain. It is in many cases a medical emergency, requiring urgent and specific diagnosis. Several causes need immediate surgical treatment. Differential diagnosis The differential diagnosis o ...

, or ileus. When taken by mouth it should be ingested with plenty of water.

Side effects

Side effects are uncommon and typically mild, and may include

stomach The stomach is a muscular, hollow organ in the gastrointestinal tract of humans and many other animals, including several invertebrates. The stomach has a dilated structure and functions as a vital organ in the digestive system. The stomach i ...

pain, abdominal cramps or

diarrhea Diarrhea, also spelled diarrhoea, is the condition of having at least three loose, liquid, or watery bowel movements each day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin ...

, Efficacy decreases with long-term use, and may cause poor bowel function. Serious allergic reactions may occur with the drug. The most severe side effect of docusate, although very rare, is rectal bleeding.drugs.com
Docusate

Interactions

Docusate might increase resorption of other drugs, for example, dantron (1,8-dihydroxyanthraquinone).

Mechanism of action

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

. It does not stay in the gastrointestinal tract, but is absorbed into the bloodstream and excreted via the

gallbladder In vertebrates, the gallbladder, also known as the cholecyst, is a small hollow organ where bile is stored and concentrated before it is released into the small intestine. In humans, the pear-shaped gallbladder lies beneath the liver, althoug ...

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.

Pharmaceutical brand names

In the U.S., docusate sodium for pharmaceutical use is available under multiple brand names: Aqualax, Calube, Colace, Colace Micro-Enema, Correctol Softgel Extra Gentle, DC-240, Dialose, Diocto, Dioctocal, Dioctosoftez, Dioctyn, Dionex, Doc-Q-Lace, Docu Soft, Docucal, Doculax, Docusoft S, DOK, DOS, Doss-Relief, DSS, Dulcolax - Stool Softener (not to be confused with another drug marketed under the Dulcolax brand, bisacodyl, which is a stimulant laxative), Ex-Lax Stool Softener, Fleet Sof-Lax, Genasoft, Kasof, Laxa-basic, Modane Soft, Octycine-100, Pedia-Lax, Preferred Plus Pharmacy Stool Softener, Regulax SS, Sulfalax Calcium, Sur-Q-Lax, Surfak Stool Softener, and Therevac-SB. Generic preparations are also available. In the UK, dioctyl sodium sulfosuccinate is sold under the brand name Docusol (Typharm Ltd) and DulcoEase (Boehringer Ingelheim). In Australia, dioctyl sodium sulfosuccinate is sold as Coloxyl and Coloxyl with senna. In India, preparations include Laxatin by Alembic, Doslax by Raptakos Laboratories, Cellubril by AstraZeneca, and Laxicon by Stadmed.

Other uses

Dioctyl sodium sulfosuccinate is used as a

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, fo ...

in a wide range of applications, often under the name Aerosol-OT. It is unusual in that it is able to form

microemulsions Microemulsions are clear, thermodynamically stable isotropic liquid mixtures of oil, water and surfactant, frequently in combination with a cosurfactant. The aqueous phase may contain salt(s) and/or other ingredients, and the "oil" may actually be a ...

without the use of co-surfactants, and it has a rich variety of aqueous-phase behavior including multiple liquid crystalline phases.

Food additive

Dioctyl sodium sulfosuccinate has been approved by the US FDA as a "generally recognized as safe" (GRAS) additive. It is used in a variety of food products, as a surface active agent, stabilizer, thickener, wetting agent, processing aid,

solubilizing agent In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solub ...

, and

. The highest amount found in food products is 0.5% by weight, which include pasteurized cheese spreads, cream cheeses and salad dressings. The FDA also approved its use as a wetting agent or solubilizer for flavoring agents in

carbonated Carbonation is the chemical reaction of carbon dioxide to give carbonates, bicarbonates, and carbonic acid. In chemistry, the term is sometimes used in place of carboxylation, which refers to the formation of carboxylic acids. In inorganic ...

and non-carbonated drinks at levels up to 10 parts per million.

Microencapsulation

Sodium docusate is the most widely used surfactant in reverse

micelle A micelle () or micella () (plural micelles or micellae, respectively) is an aggregate (or supramolecular assembly) of surfactant amphipathic lipid molecules dispersed in a liquid, forming a colloidal suspension (also known as associated col ...

encapsulation studies.

Non-medical brand names

As a surfactant, docusate sodium is or has been commercialized under many brand names, including DSSj Aerosol OT, Alphasol OT, Colace, Complemix, Coprol, Dioctylal, Dioctyl-Medo Forte, Diotilan, Diovac, Disonate, Doxinate, Doxol, Dulsivac, Molatoc, Molofac, Nevax, Norval, Regutol, Softili, Solusol, Sulfimel DOS, Vatsol OT, Velmol, and Waxsol

Chemistry

Structure and properties

The

structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bond ...

of the docusate anion is , where R is the 2-ethylhexyl group . The

conjugate acid A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...

can be described as the twofold

carboxyl In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxyl ...

ate ester of sulfosuccinic acid with

2-ethylhexanol 2-Ethylhexanol (abbreviated 2-EH) is an organic compound with formula CHO. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale ...

. The compound is a white, wax-like, plastic solid, with an odor suggestive of

octyl alcohol Octanols are alcohols with the formula C8H17OH. A simple and important member is 1-octanol, with an unbranched chain of carbons. Other commercially important octanols are 2-octanol and 2-ethylhexanol 2-Ethylhexanol (abbreviated 2-EH) is an orga ...

. It starts to decompose at about 220 °C. Solubility of dioctyl sodium sulfosuccinate in water is 14 g/L at 25 °C, increasing to 55 g/L at 70 °C. Solubility is better in less polar solvents: 1:30 in

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a h ...

, 1:1 in

chloroform Chloroform, or trichloromethane, is an organic compound with formula C H Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to PTFE. It is also a precursor to various re ...

and diethylether, and practically unlimited in

petroleum ether Petroleum ether is the petroleum fraction consisting of aliphatic hydrocarbons and boiling in the range 35–60 °C, and commonly used as a laboratory solvent. Despite the name, petroleum ether is not classified as an ether; the term is used ...

(25 °C). It also is highly soluble in

glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids know ...

, although this is a rather polar solvent. It is also highly soluble in

xylene In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are sub ...

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated om ...

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible wi ...

, diacetone alcohol, methanol,

isopropanol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group (chemical formula ) it is the simp ...

, 2-butanol, methyl acetate,

ethyl acetate Ethyl acetate ( systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues ...

, furfurol, and

vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, ...

s. The

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

groups are easily cleaved under

basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version was created by John G. Kemeny and Thomas E. Kurtz at Dartmouth College ...

conditions, but are stable against acids.

Synthesis

Sodium dioctyl sulfosuccinate can be obtained by treating dioctyl maleate with

sodium bisulfite Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite in fact is not a real compound, but a mixture of salts that dissolve in water to give solutions ...

. The

bisulfite The bisulfite ion (IUPAC-recommended nomenclature: hydrogensulfite) is the ion . Salts containing the ion are also known as "sulfite lyes". Sodium bisulfite is used interchangeably with sodium metabisulfite (Na2S2O5). Sodium metabisulfite diss ...

anion adds to the

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

: : +

Toxicity

Ingestion may cause the side effects described above, such as diarrhea, intestinal bloating, and occasionally cramping pains. Dioctyl sodium sulfosuccinate is not known to be

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subst ...

ic,

mutagen In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer i ...

ic, or teratogenic.

Marine species

Dioctyl sodium sulfosuccinate is of low toxicity for

crustacean Crustaceans (Crustacea, ) form a large, diverse arthropod taxon which includes such animals as decapods, seed shrimp, branchiopods, fish lice, krill, remipedes, isopods, barnacles, copepods, amphipods and mantis shrimp. The crustacean gro ...

s such as the

hermit crab Hermit crabs are anomuran decapod crustaceans of the superfamily Paguroidea that have adapted to occupy empty scavenged mollusc shells to protect their fragile exoskeletons. There are over 800 species of hermit crab, most of which possess an a ...

'' Clibanarius erythropus'' and the shrimp '' Crangon crangon''. Toxicity for molluscs varies widely, with 48-hour LD₅₀ found between 5 mg/L for the common limpet and 100 mg/L for the common periwinkle. Various species of

phytoplankton Phytoplankton () are the autotrophic (self-feeding) components of the plankton community and a key part of ocean and freshwater ecosystems. The name comes from the Greek words (), meaning 'plant', and (), meaning 'wanderer' or 'drifter'. P ...

have an LD₅₀ around 8 mg/L. In a 2010 study, dioctyl sodium sulfosuccinate exhibited higher toxicity against bacteria (''

Vibrio fischeri ''Aliivibrio fischeri'' (also called ''Vibrio fischeri'') is a Gram-negative, rod-shaped bacterium found globally in marine environments. This species has bioluminescent properties, and is found predominantly in symbiosis with various marine a ...

'', ''

Anabaena ''Anabaena'' is a genus of filamentous cyanobacteria that exist as plankton. They are known for nitrogen-fixing abilities, and they form symbiotic relationships with certain plants, such as the mosquito fern. They are one of four genera of cy ...

'' sp.) and algae ('' Pseudokirchneriella subcapitata'') than did a number of fluorinated surfactants (

PFOS Perfluorooctanesulfonic acid (PFOS) ( conjugate base perfluorooctanesulfonate) is a chemical compound having an eight- carbon fluorocarbon chain and a sulfonic acid functional group and thus a perfluorosulfonic acid. It is an anthropogenic (man ...

, PFOA, or PFBS). Measuring

bioluminescence Bioluminescence is the production and emission of light by living organisms. It is a form of chemiluminescence. Bioluminescence occurs widely in marine vertebrates and invertebrates, as well as in some fungi, microorganisms including some ...

inhibition of the bacteria and growth inhibition of the algae, the LD₅₀ were in the range of 43–75 mg/L. Combinations of the fluorinated compounds with dioctyl sodium sulfosuccinate showed mid to highly synergistic effects in most settings, meaning that such combinations are significantly more toxic than the individual substances.

Freshwater species

The substance is highly toxic for

rainbow trout The rainbow trout (''Oncorhynchus mykiss'') is a species of trout native to cold-water tributaries of the Pacific Ocean in Asia and North America. The steelhead (sometimes called "steelhead trout") is an anadromous (sea-run) form of the coast ...

with a median lethal concentration (LC₅₀) of 0.56 mg/L after 48 hours for the pure substance. It is only slightly to moderately toxic for rainbow trout fingerlings, and slightly toxic for harlequin rasboras (LC₅₀ 27 mg/L of a 60% formulation after 48 hours).

References

External links

* *
Stool Softeners
at the N.I.H.

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