Dioctyl sodium sulfosuccinate
Encyclopedia
Dioctyl sodium sulfosuccinate or docusate sodium (INN
, icon) – often referred to as DSS, Aerosol OT or AOT – is a common ingredient in consumer products, especially laxatives of the stool softener type. It is also used as an emulsifying, wetting, and dispersing
agent, as a pesticide
, as well as a component of the oil dispersant Corexit
which was used in the Deepwater Horizon oil spill
of 2010. It is an anionic surfactant
, a substance that lowers the surface tension
of water.
Docusate calcium
and docusate potassium
, as well as other dioctyl sulfosuccinate salts, are also widely used in the same areas.
, in painful anorectal
conditions such as hemorrhoids and anal fissures, and for people avoiding straining during bowel movements. Patients taking ducosate should drink plenty of water to irrigate the bowel, thereby increasing motility
. Given orally, the effects are usually seen 1 to 3 days after the first dose. Given rectally, as an enema
or suppository
, a bowel movement usually occurs within 5 to 20 minutes.
The drug may be used in people who are undergoing opioid pain therapy, are opioid dependent, or on opioid replacement therapy, though prolonged use may cause irritation of the gastrointestinal tract. Data supporting its efficacy in treating chronic constipation is lacking.
, acute abdomen
or ileus
. It is not suitable for the treatment of chronic obstipation.
solvents: 1:30 in ethanol
, 1:1 in chloroform
and diethylether, and practically unlimited in petroleum ether
(25 °C). It is also highly soluble in glycerol
, although this is a rather polar solvent.
The ester
groups are easily cleaved under basic
conditions, but are stable against acid
s.
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
.
(1,8-dihydroxyanthraquinone).
ic, mutagen
ic or teratogenic.
s like the hermit crab
Clibanarius erythropus
and the shrimp Crangon crangon
. The median lethal dose (LD50) for these species is about 100 mg/l
of a docusate containing formulation after 48 hours of exposition, although the concentration of the formulation is not specified in the study.
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
have an LD50 of around 8 mg/l. All of these doses refer to the mentioned formulation, not the pure chemical.
In a 2010 study, dioctyl sodium sulfosuccinate exhibited higher toxicity against bacteria (Vibrio fischeri
, Anabaena
sp.) and algae (Pseudokirchneriella subcapitata) than a number of fluorinated surfactants (PFOS, PFOA
, PFBS). Measuring bioluminescence
inhibition of the bacteria and growth inhibition of the algae, the ED50
were in the range of 43–75 mg/l. Combinations of the fluorinated compounds with DSS showed mid to highly synergistic effects in most settings, meaning that such combinations are significantly more toxic than the individual substances.
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 rasbora
s (LC50 27 mg/l of a 60% formulation after 48 hours).
In the UK it sold under the brand name Docusol (Typharm Ltd) and DulcoEase (Boehringer Ingelheim).
In Australia it is sold as Coloxyl, or Coloxyl with senna
.
International Nonproprietary Name
An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...
, icon) – often referred to as DSS, Aerosol OT or AOT – is a common ingredient in consumer products, especially laxatives of the stool softener type. It is also used as an emulsifying, wetting, and dispersing
Dispersion (chemistry)
A dispersion is a system in which particles are dispersed in a continuous phase of a different composition . See also emulsion. A dispersion is classified in a number of different ways, including how large the particles are in relation to the particles of the continuous phase, whether or not...
agent, as a pesticide
Pesticide
Pesticides are substances or mixture of substances intended for preventing, destroying, repelling or mitigating any pest.A pesticide may be a chemical unicycle, biological agent , antimicrobial, disinfectant or device used against any pest...
, as well as a component of the oil dispersant Corexit
Corexit
Corexit is a product line of solvents primarily used as a dispersant for breaking up oil slicks. It is produced by Nalco Holding Company which is associated with BP and Exxon. Corexit was the most-used dispersant in the Deepwater Horizon oil spill in the Gulf of Mexico, with COREXIT 9527 having...
which was used in the Deepwater Horizon oil spill
Deepwater Horizon oil spill
The Deepwater Horizon oil spill is an oil spill in the Gulf of Mexico which flowed unabated for three months in 2010, and continues to leak fresh oil. It is the largest accidental marine oil spill in the history of the petroleum industry...
of 2010. It is an anionic surfactant
Surfactant
Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids, or that between a liquid and a solid...
, a substance that lowers the surface tension
Surface tension
Surface tension is a property of the surface of a liquid that allows it to resist an external force. It is revealed, for example, in floating of some objects on the surface of water, even though they are denser than water, and in the ability of some insects to run on the water surface...
of water.
Docusate calcium
Calcium
Calcium is the chemical element with the symbol Ca and atomic number 20. It has an atomic mass of 40.078 amu. Calcium is a soft gray alkaline earth metal, and is the fifth-most-abundant element by mass in the Earth's crust...
and docusate potassium
Potassium
Potassium is the chemical element with the symbol K and atomic number 19. Elemental potassium is a soft silvery-white alkali metal that oxidizes rapidly in air and is very reactive with water, generating sufficient heat to ignite the hydrogen emitted in the reaction.Potassium and sodium are...
, as well as other dioctyl sulfosuccinate salts, are also widely used in the same areas.
Clinical use
Docusate is used to make stools softer and easier to pass. It is used to treat constipationConstipation
Constipation refers to bowel movements that are infrequent or hard to pass. Constipation is a common cause of painful defecation...
, in painful anorectal
Anorectal
Not to be confused with anorexia.Anorectal anomalies are medical problems affecting the structure of the anus and rectum. A person with an anorectal problem would have some sort of deformative feature of the anus or rectum, collectively known as an anorectal malformation.Examples of anorectal...
conditions such as hemorrhoids and anal fissures, and for people avoiding straining during bowel movements. Patients taking ducosate should drink plenty of water to irrigate the bowel, thereby increasing motility
Motility
Motility is a biological term which refers to the ability to move spontaneously and actively, consuming energy in the process. Most animals are motile but the term applies to single-celled and simple multicellular organisms, as well as to some mechanisms of fluid flow in multicellular organs, in...
. Given orally, the effects are usually seen 1 to 3 days after the first dose. Given rectally, as an enema
Enema
An enema is the procedure of introducing liquids into the rectum and colon via the anus. The increasing volume of the liquid causes rapid expansion of the lower intestinal tract, often resulting in very uncomfortable bloating, cramping, powerful peristalsis, a feeling of extreme urgency and...
or suppository
Suppository
A suppository is a drug delivery system that is inserted into the rectum , vagina or urethra , where it dissolves.They are used to deliver both systemically-acting and locally-acting medications....
, a bowel movement usually occurs within 5 to 20 minutes.
The drug may be used in people who are undergoing opioid pain therapy, are opioid dependent, or on opioid replacement therapy, though prolonged use may cause irritation of the gastrointestinal tract. Data supporting its efficacy in treating chronic constipation is lacking.
Available forms
Docusate sodium is administered orally or rectally; in tablets, capsules, suppositories and enemas. It is also used as an emulsifier and dispersant in topical preparations.Other uses
- Dioctyl sodium sulfosuccinate is a pesticidePesticidePesticides are substances or mixture of substances intended for preventing, destroying, repelling or mitigating any pest.A pesticide may be a chemical unicycle, biological agent , antimicrobial, disinfectant or device used against any pest...
used popularly for crops of olives, almonds, wine grapes, corn and oranges. - It is used as an excipientExcipientAn excipient is generally a pharmacologically inactive substance used as a carrier for the active ingredients of a medication. In many cases, an "active" substance may not be easily administered and absorbed by the human body; in such cases the substance in question may be dissolved into or...
in the production of tabletTabletA tablet is a pharmaceutical dosage form. It comprises a mixture of active substances and excipients, usually in powder form, pressed or compacted from a powder into a solid dose...
s (as a lubricantLubricantA lubricant is a substance introduced to reduce friction between moving surfaces. It may also have the function of transporting foreign particles and of distributing heat...
) and suspensionSuspension (chemistry)In chemistry, a suspension is a heterogeneous fluid containing solid particles that are sufficiently large for sedimentation. Usually they must be larger than 1 micrometer. The internal phase is dispersed throughout the external phase through mechanical agitation, with the use of certain...
s (as an emulsifier). - It is the most widely used surfactant in reverse micelleMicelleA micelle is an aggregate of surfactant molecules dispersed in a liquid colloid. A typical micelle in aqueous solution forms an aggregate with the hydrophilic "head" regions in contact with surrounding solvent, sequestering the hydrophobic single tail regions in the micelle centre. This phase is...
encapsulationMolecular encapsulationMolecular encapsulation in supramolecular chemistry is the confinement of a guest molecule inside the cavity of a supramolecular host molecule...
studies. - Docusate sodium, when used in conjunction with irrigation, is also an effective means of earwax removal.
Contraindications
Docusate is contraindicated in patients with appendicitisAppendicitis
Appendicitis is a condition characterized by inflammation of the appendix. It is classified as a medical emergency and many cases require removal of the inflamed appendix, either by laparotomy or laparoscopy. Untreated, mortality is high, mainly because of the risk of rupture leading to...
, acute abdomen
Acute abdomen
The term acute abdomen refers to a sudden, severe abdominal pain of unclear etiology that is less than 24 hours in duration. It is in many cases a medical emergency, requiring urgent and specific diagnosis...
or ileus
Ileus
Ileus is a disruption of the normal propulsive ability of the gastrointestinal tract.Ileus is commonly defined simply as bowel obstruction. However, authoritative sources define it as decreased motor activity of the GI tract due to non-mechanical causes...
. It is not suitable for the treatment of chronic obstipation.
Side effects
Possible side effects are typically mild and include stomach pain, diarrhea, or cramping. Serious allergic reactions can occur with the drug. The most severe side effect of docusate, although very rare, is rectal bleeding.Physical and chemical properties
Solubility of dioctyl sodium sulfosuccinate in water is 1:70 (14 g/l) at 25 °C, increasing to 1:20 at 70 °C. Solubility is better in less polarChemical polarity
In chemistry, polarity refers to a separation of electric charge leading to a molecule or its chemical groups having an electric dipole or multipole moment. Polar molecules interact through dipole–dipole intermolecular forces and hydrogen bonds. Molecular polarity is dependent on the difference in...
solvents: 1:30 in ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
, 1:1 in chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...
and diethylether, and practically unlimited in petroleum ether
Petroleum ether
Petroleum ether, also known as benzine, VM&P Naphtha, Petroleum Naphtha, Naphtha ASTM, Petroleum Spirits, X4 or Ligroin, is a group of various volatile, highly flammable, liquid hydrocarbon mixtures used chiefly as nonpolar solvents...
(25 °C). It is also highly soluble in glycerol
Glycerol
Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...
, although this is a rather polar solvent.
The ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
groups are easily cleaved under basic
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
conditions, but are stable against acid
Acid
An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...
s.
Pharmacokinetics and mechanism of action
Docusate does not stay in the gastrointestinal tract, but is absorbed into the bloodstream and excreted via the gallbladderGallbladder
In vertebrates the gallbladder is a small organ that aids mainly in fat digestion and concentrates bile produced by the liver. In humans the loss of the gallbladder is usually easily tolerated....
after undergoing extensive metabolism.
The effect of docusate may not necessarily be all due to its surfactant properties. Perfusion
Perfusion
In physiology, perfusion is the process of nutritive delivery of arterial blood to a capillary bed in the biological tissue. The word is derived from the French verb "perfuser" meaning to "pour over or through."...
studies suggest that docusate inhibits fluid absorption or stimulates secretion in the portion of the small intestine known as the jejunum
Jejunum
The jejunum is the middle section of the small intestine in most higher vertebrates, including mammals, reptiles, and birds. In fish, the divisions of the small intestine are not as clear and the terms middle intestine or mid-gut may be used instead of jejunum.The jejunum lies between the duodenum...
.
Interactions
Docusate should not be used in addition to mineral oil as the emulsifier will result in mineral oil being absorbed rather than functioning as a lubricant for the bowel walls, possibly resulting in foreign body granulomas. The substance might also increase resorption of other drugs, for example dantronDantron
1,8-Dihydroxyanthraquinone is an organic substance with formula , formally derived from anthraquinone by the replacement of two hydrogen atoms by hydroxyl groups...
(1,8-dihydroxyanthraquinone).
Toxicity
Toxicity for different species varies in a wide range, but dioctyl sulfosuccinate biodegrades quickly in soil and water, a typical finding being >90% in 12 to 17 days. In the atmosphere, it is destroyed by a photochemical reaction with an estimated half-life of 18 hours.In humans
Dioctyl sodium sulfosuccinate is a strong irritant for eyes and lungs, and also a skin irritant. Ingestion can cause the side effects described above, such as diarrhea, intestinal bloating and occasionally cramping pains. DSS is not known to be carcinogenCarcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
ic, mutagen
Mutagen
In genetics, a mutagen is a physical or chemical agent that changes the genetic material, usually DNA, of an organism and thus increases the frequency of mutations above the natural background level. As many mutations cause cancer, mutagens are therefore also likely to be carcinogens...
ic or teratogenic.
In marine species
Dioctyl sodium sulfosuccinate has been determined to be of low toxicity for crustaceanCrustacean
Crustaceans form a very large group of arthropods, usually treated as a subphylum, which includes such familiar animals as crabs, lobsters, crayfish, shrimp, krill and barnacles. The 50,000 described species range in size from Stygotantulus stocki at , to the Japanese spider crab with a leg span...
s like the hermit crab
Hermit crab
Hermit crabs are decapod crustaceans of the superfamily Paguroidea. Most of the 1100 species possess an asymmetrical abdomen which is concealed in an empty gastropod shell that is carried around by the hermit crab.-Description:...
Clibanarius erythropus
Clibanarius erythropus
Clibanarius erythropus is a species of hermit crab that lives in rockpools and sublittoral waters. It is found in the Mediterranean Sea, Black Sea and eastern Atlantic Ocean from the Azores to Brittany, and as far north as the Channel Islands. Individuals may grow up to a carapace length of...
and the shrimp Crangon crangon
Crangon crangon
Crangon crangon is a commercially important species of shrimp fished mainly in the southern North Sea, although also found in the Irish Sea, Baltic Sea, Mediterranean Sea and Black Sea, as well as off much of Scandinavia and parts of Morocco's Atlantic coast...
. The median lethal dose (LD50) for these species is about 100 mg/l
Litre
pic|200px|right|thumb|One litre is equivalent to this cubeEach side is 10 cm1 litre water = 1 kilogram water The litre is a metric system unit of volume equal to 1 cubic decimetre , to 1,000 cubic centimetres , and to 1/1,000 cubic metre...
of a docusate containing formulation after 48 hours of exposition, although the concentration of the formulation is not specified in the study.
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
Common Periwinkle
The common periwinkle or winkle, scientific name Littorina littorea, is a species of small edible sea snail, a marine gastropod mollusk which has gills and an operculum, and is classified within the family Littorinidae, the periwinkles....
. Various species of phytoplankton
Phytoplankton
Phytoplankton are the autotrophic component of the plankton community. The name comes from the Greek words φυτόν , meaning "plant", and πλαγκτός , meaning "wanderer" or "drifter". Most phytoplankton are too small to be individually seen with the unaided eye...
have an LD50 of around 8 mg/l. All of these doses refer to the mentioned formulation, not the pure chemical.
In a 2010 study, dioctyl sodium sulfosuccinate exhibited higher toxicity against bacteria (Vibrio fischeri
Vibrio fischeri
Vibrio fischeri is a gram-negative rod-shaped bacterium found globally in marine environments. V. fischeri has bioluminescent properties, and is found predominantly in symbiosis with various marine animals, such as the bobtail squid. It is heterotrophic and moves by means of flagella. Free living...
, Anabaena
Anabaena
Anabaena is a genus of filamentous cyanobacteria that exists as plankton. It is known for its nitrogen fixing abilities, and they form symbiotic relationships with certain plants, such as the mosquito fern. They are one of four genera of cyanobacteria that produce neurotoxins, which are harmful to...
sp.) and algae (Pseudokirchneriella subcapitata) than a number of fluorinated surfactants (PFOS, PFOA
Perfluorooctanoic acid
Perfluorooctanoic acid , also known as C8 and perfluorooctanoate, is a synthetic, stable perfluorinated carboxylic acid and fluorosurfactant. One industrial application is as a surfactant in the emulsion polymerization of fluoropolymers. It has been used in the manufacture of such prominent...
, PFBS). Measuring bioluminescence
Bioluminescence
Bioluminescence is the production and emission of light by a living organism. Its name is a hybrid word, originating from the Greek bios for "living" and the Latin lumen "light". Bioluminescence is a naturally occurring form of chemiluminescence where energy is released by a chemical reaction in...
inhibition of the bacteria and growth inhibition of the algae, the ED50
ED50
ED 50 is a geodetic datum which was defined after World War II for the international connection of geodetic networks....
were in the range of 43–75 mg/l. Combinations of the fluorinated compounds with DSS showed mid to highly synergistic effects in most settings, meaning that such combinations are significantly more toxic than the individual substances.
In freshwater species
The substance is highly toxic for rainbow troutRainbow trout
The rainbow trout is a species of salmonid native to tributaries of the Pacific Ocean in Asia and North America. The steelhead is a sea run rainbow trout usually returning to freshwater to spawn after 2 to 3 years at sea. In other words, rainbow trout and steelhead trout are the same species....
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 rasbora
Harlequin rasbora
The Harlequin Rasbora a small fish belonging to the Family Cyprinidae, subfamily Rasborinae, which was originally given the scientific name of Rasbora heteromorpha...
s (LC50 27 mg/l of a 60% formulation after 48 hours).
Trade marks
In the U.S. it 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, Ex-Lax Stool Softener, Fleet Sof-Lax, Genasoft, Kasof, Laxa-basic, Modane Soft, Octycine-100, 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 it sold under the brand name Docusol (Typharm Ltd) and DulcoEase (Boehringer Ingelheim).
In Australia it is sold as Coloxyl, or Coloxyl with senna
Senna (genus)
Senna , the sennas, is a large genus of flowering plants in the family Fabaceae, subfamily Caesalpinioideae. This diverse genus is native throughout the tropics, with a small number of species reaching into temperate regions. The number of species is usually estimated to be about 260, but some...
.
External links
- Stool Softeners at the N.I.H.National Institutes of HealthThe National Institutes of Health are an agency of the United States Department of Health and Human Services and are the primary agency of the United States government responsible for biomedical and health-related research. Its science and engineering counterpart is the National Science Foundation...
PubMedPubMedPubMed is a free database accessing primarily the MEDLINE database of references and abstracts on life sciences and biomedical topics. The United States National Library of Medicine at the National Institutes of Health maintains the database as part of the Entrez information retrieval system...
Health resource.