Sodium Diethylhexyl Sulfosuccinate. Docusate is the common chemical and pharmaceutical name of the anion bis(2-ethylhexyl) sulfosuccinate, also commonly called dioctyl sulfosuccinate (DOSS). All-purpose surfactant, wetting agent, and solubilizer used in the drug, cosmetics, and food industries. It has also been used in laxatives and as cerumenolytics. It is usually administered as either the calcium, potassium, or sodium salt.
DIETHYLHEXYL SODIUM SULFOSUCCINATE
DIETHYLHEXYL SODIUM SULFOSUCCINATE is classified as :
Cleansing
Emulsifying
Hydrotrope
Surfactant
CAS Number 577-11-7
EINECS/ELINCS No: 209-406-4
COSING REF No: 75723
Chem/IUPAC Name: Docusate sodium
Sodium Diethylhexyl Sulfosuccinate;CAS Number 577-11-7;Chem/IUPAC Name: Docusate sodium;Sodium sulfosuccinic acid dioctyl ester;Sodium di-n-octyl sulfosuccinate; DOS; Sodium dioctyl sulfosuccinate;Dioctyl sodium sulphosuccinate
Salts of this anion, especially docusate sodium, are widely used in medicine as laxatives and as stool softeners, by mouth or rectally.
Docusate sodium is on the WHO List of Essential Medicines. It is a widely available and relatively inexpensive generic medication, with more than six million prescriptions in the US in 2017.
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
Wetting Agents (Stool Softeners and Lubricants)
Docusate sodium (dioctyl sodium sulfosuccinate) and docusate calcium (dioctyl calcium sulfosuccinate) act like detergents and are used to soften the stool when it is desirable to lessen the discomfort or the strain of defecation.
CAS Number: 577-11-7
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 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 quicky popularized under the name Doxinate.
Medical use
Constipation
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, 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 placebo for improving constipation.
Others have found it 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.
Other medical uses
Docusate sodium, when used with ear syringing, may help with earwax removal, particularly in the case of impaction.
Sodium docusate is also used as a lubricant in the production of tablets and as an emulsifier in topical preparations and other suspensions.
Precautions and contraindications
Docusate sodium is approved and recommended as safe during pregnancy and breastfeeding.
Docusate is not recommended in people with appendicitis, acute abdomen, 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 pain, abdominal cramps or diarrhea, 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.
Interactions
Docusate might increase resorption of other drugs, for example, dantron (1,8-dihydroxyanthraquinone).
Mechanism of action
Docusate sodium works by allowing more water to be absorbed by the stool.
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.[medical citation needed]
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 in a wide range of applications, often under the name Aerosol-OT.[5][23] It is unusual in that it is able to form microemulsions without the use of co-surfactants, and it has a rich variety of aqueous-phase behavior including multiple liquid crystalline phases.[24]
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, emulsifier, and dispersant.
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 and non-carbonated drinks at levels up to 10 parts per million.
Microencapsulation
Sodium docusate is the most widely used surfactant in reverse micelle 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 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.
The compound is a white, wax-like, plastic solid, with an odor suggestive of octyl alcohol. 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.[28] Solubility is better in less polar solvents: 1:30 in ethanol, 1:1 in chloroform and diethylether, and practically unlimited in petroleum ether (25 °C). It also is highly soluble in glycerol, although this is a rather polar solvent. It is also highly soluble in xylene, oleic acid, acetone, diacetone alcohol, methanol, isopropanol, 2-butanol, methyl acetate, ethyl acetate, furfurol, and vegetable oils.[28]
The ester groups are easily cleaved under basic conditions, but are stable against acids.
Dioctyl sodiosulfosuccinate
Dioctyl sodium sulphosuccinate
Dioctyl sulfosuccinate, sodium salt
Sodium bis(octyl)sulfosuccinate
Sodium di-n-octyl sulfosuccinate
Sodium dioctyl sulfosuccinate
Sodium O,O-dioctylsulfosuccinic acid
Sodium sulfosuccinic acid dioctyl ester
Sulfosuccinic acid 1,4-dioctyl ester sodium salt
Bu-cerumen
Texapon DOS
DI-N-OCTYL SODIUM SULFOSUCCINATE
Solbaleite
Butyl-cerumen
1639-66-3
Neocol SW 30
Caswell No. 392I
Elfanol 883
Sodium di-n-octylsulfosuccinate
HSDB 4086
Butanedioic acid, sulfo-, 1,4-dioctyl ester, sodium salt
NSC 7779
EINECS 216-684-0
EPA Pesticide Chemical Code 079027
Dioktylester sulfojantaranu sodneho [Czech]
Succinic acid, sulfo-, dioctyl ester, sodium salt
Succinic acid, sulfo-, 1,4-dioctyl ester, sodium salt
1,4-Bis(n-octyl) sulfobutanedioate, sodium salt
MKC
Sulfobutanedioic acid, 1,4-di(n-octyl) ester, sodium salt
Butanedioic acid, 2-sulfo-, 1,4-dioctyl ester, sodium salt (1:1)
sulfonated aliphatic polyester
Dioktylester sulfojantaranu sodneho
sodium dioctyl sulfosuccinate
SCHEMBL22809
DTXSID7041881
2-(Sodiosulfo)succinic acid dioctyl
LS-147500
Q27260677
monawetmo-70
monawetmo-70rp
monawetmo-84r2w
PenetratingagentT
Rapid Penetrant T
di-secovtyl naleate
DICAPRYL SODIUM SULFOSUCCINATE
sodiumdi-n-octylsulfosuccinate
di-n-octylsodiumsulfosuccinate
Sodiosulfosuccinic acid dioctyl
dioktylestersulfojantaranusodneho
Sodium diethylhexyl sulfosuccinate
2-(Sodiosulfo)succinic acid dioctyl
sodium di-sec-octyl maleace sulfonate
succinicacid,sulfo-,dioctylester,sodiumsalt
sulfosuccinicacid1,4-dioctylestersodiumsalt
2-(Sodiooxysulfonyl)butanedioic acid dioctyl
(Sodiooxysulfonyl)succinic acid dioctyl ester
2-Sulfosuccinic acid 1,4-dioctyl 2-sodium salt
succinicacid,sulfo-,1,4-dioctylester,sodiumsalt
Butanedioicacid,sulfo-,1,4-dioctylester,sodiumsalt
2-(Sodiooxysulfonyl)butanedioic acid dioctyl ester
Butanedioic acid,2-sulfo-, 1,4-dioctyl ester, sodiuM salt (1:1) CAS No. 1639-66-3"
