DIOCTYL SODIUM SULFOSUCCINATE
Dioctyl sodium sulfosuccinate is a widely used anionic surfactant and stool softener primarily employed to treat constipation by increasing the water and fat content in the stool, thereby facilitating easier passage.
Dioctyl sodium sulfosuccinate acts as a wetting agent by reducing the surface tension of liquids, allowing water and lipids to penetrate the stool more effectively.
Despite its widespread use, prolonged reliance on Dioctyl sodium sulfosuccinate is discouraged to avoid potential dependency, emphasizing its role as a short-term solution for occasional constipation.
CAS Number: 577-11-7
EC Number: 209-406-4
Molecular Formula: C20H37O7S
Molar mass: 421.57 g·mol−1
Synonyms: Docusate sodium, 577-11-7, Dioctyl sodium sulfosuccinate, Aerosol OT, Dioctylal, Diotilan, Disonate, Molatoc, Regutol, Velmol, Doxol, Nevax, Dialose, Doxinate, Soliwax, Molcer, Waxsol, Adekacol EC 8600, Docusate (Sodium), Constonate, Mervamine, Clestol, Defilin, Obston, Requtol, Docusate sodium salt, Diox, Modane Soft, Alcopol O, Sulfimel DOS, Manoxal OT, Manoxol OT, Aerosol AOT, Aerosol GPG, Wetaid SR, Aerosol OT-A, Colace, Laxinate 100, Sanmorin OT 70, Triton GR 7, Triton GR-5, Aerosol OT 70PG, Aerosol OT 75, Celanol DOS 65, Celanol DOS 75, Coloxyl, Comfolax, Coprola, Dioctyl, Docolace, Docuprene, Dulcivac, Eurowet, Humifen WT 27G, Solusol-75%, Silace, Bloat treatment, Docusato sodico, Nikkol OTP 70, Aerosol A 501, Alkasurf SS-O 75, Solusol-100%, Docusate sodique, Nekal WT-27, Berol 478, Docusatum natricum, Empimin op70, Sanmorin ot 70n, Bis(2-ethylhexyl) sulfosuccinate sodium salt, Natrii dioctylsulfosuccinas, Tex-Wet 1001, Airrol ct-1, Doc Q Lace, Mackanate dos-70, Nikkol otp-75, Gemtex pa-70, Rapisol a 30, Triton gr-pg 70, Sodium dioctyl sulphosuccinate, Nissan rapisol a 30, Jamylene, Bis(2-ethylhexyl) sodium sulfosuccinate, Sodium 2-ethylhexylsulfosuccinate, Sodium bis(2-ethylhexyl) sulfosuccinate, HSDB 3065, Ins no.480, Monawet mo 65-150, 2-Ethylhexyl sulfosuccinate sodium, EINECS 209-406-4, Ins-480, Dioctyl sodium sulphosuccinat, Sodium 1,4-bis(2-ethylhexyl) sulfosuccinate, UNII-F05Q2T2JA0, MFCD00012455, Dioctyl ester of sodium sulfosuccinate, Bis(2-ethylhexyl)sodium sulfosuccinate, Di-(2-ethylhexyl) sodium sulfosuccinate, Sodium di-(2-ethylhexyl) sulfosuccinate, Docusate sodique [INN-French], Docusato sodico [INN-Spanish], F05Q2T2JA0, Docusatum natricum [INN-Latin], DTXSID8022959, Dioctyl ester of sodium sulfosuccinic acid, AI3-00239, Diethylhexyl Sodium Sulfosuccinate, Sodium sulfodi-(2-ethylhexyl)-sulfosuccinate, CHEMAX DOSS/75E, NSC-760404, Butanedioic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester, sodium salt, CHEBI:4674, DTXCID102959, Bis-2-ethylhexylester sulfojantaranu sodneho, E 480, E-480, sodium 1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonate, EC 209-406-4, Sol sodowej sulfobursztynianu dwu-2-etyloheksylowego, sodium docusate, 1,4-Bis(2-ethylhexyl)sulfobutanedioate, sodium salt, NSC 760404, AOT, Docusate sodium [USAN:USP:INN:BAN], SBO, Sodium Di(2-ethylhexyl) Sulfosuccinate, Diomedicone, Complemix, Dioctlyn, Diosuccin, Dulsivac, Laxinate, Molofac, Sobital, Coprol, Diovac, Konlax, Kosate, Softil, Revac, AEC DIETHYLHEXYL SODIUM SULFOSUCCINATE, Alphasol OT, DOCUSATE SODIUM (II), DOCUSATE SODIUM [II], Docusate sodique (INN-French), Docusato sodico (INN-Spanish), Sulfosuccinic acid bis(2-ethylhexyl) ester sodium salt, DESS, Monawet MD 70E, DOCUSATE SODIUM (MART.), DOCUSATE SODIUM [MART.], Docusatum natricum (INN-Latin), DOCUSATE SODIUM (USP-RS), DOCUSATE SODIUM [USP-RS], Geriplex, Unilax, Sodium 1,4-bis((2-ethylhexyl)oxy)-1,4-dioxobutane-2-sulfonate, Dioctyl sodium sulfosuccinate (JAN), Dialose Plus, Senokot S, Correctol Caplets, Correctol Tablets, DOCUSATE SODIUM (USP IMPURITY), DOCUSATE SODIUM [USP IMPURITY], Senokap DSS, Docusate sodium (USAN:USP:INN:BAN), DOCUSATE SODIUM (USP MONOGRAPH), DOCUSATE SODIUM [USP MONOGRAPH], D-S-S, CAS-577-11-7, DIOCTYL SODIUM SULFOSUCCINATE [JAN], Correctol Extra Gentle Tablets, NCGC00164140-03, SV 102, Promolaxin, Colistat, Prenexa, Purgasol, Vinacol, natrii docusas, Bis(2-ethylhexyl) S-sodium sulfosuccinate, DocuSol, Colace Clear, DocQLace, Enemeez Kids, Docu Liquid, Single-Use, Sodium 1,4-bis(2-ethylhexyl)sulfosuccinate, 1,4-Bis(2-ethylhexyl) sodium sulfosuccinate, DocuSol Kids, Senexon-S, docusato de sodio, Docusate sodium; Sodium 1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonate, Folca[s care pme, Folcal DHA, Senna-S, Di(2-ethylhexyl)sulfosuccinic acid, sodium salt, Betr stool softener, Bis(ethylhexyl) ester of sodium sulfosuccinic acid, CVS Stool Softener, Docusate Mini Enema, HEB Stool Softener, Bis-2-ethylhexylester sulfojantaranu sodneho [Czech], Colace (TN), Laxa-basic 100, Sodium di(2-ethylhexyl)sulfosuccinate, Clear Stool Softener, ENEMEEZ, Winco Stool Softener, Gentle Stool softener, Sulfosuccinic acid, bis(2-ethylhexyl)ester sodium salt, Kroger Stool Softener, Stool Softener Liquid, BLOAT RELEASE, STOOL SOFTNER, Docusate Sodium Liquid, PET-ENEMA, Topcare Stool Softener, DISPOSABLE ENEMA, DEH Na SS, DEH-Na-SS, Dulcolax Stool Softener, FELINE PET-EMA, PET-EMA, Phillips Stool Softener, Stool Softener Laxative, H E B Stool Softener, Sol sodowej sulfobursztynianu dwu-2-etyloheksylowego [Polish], Docusate sodium (USP), Docusate Sodium 100mg, Docusate Sodium 250mg, Walgreens Stool Softener, basic care stool softener, good sense stool softener, PlusPHARMAStool Softener, Succinic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester, sodium salt, NCGC00183136-01, CVS Health Stool Softener, Stool SoftenerGentle Relief, betr remedies stool softener, SCHEMBL4113, Gentle Relief Stool Softner, Gentle Relief Stool Softnet, DQZATE STOOL SOFTENER, healthy mamaMOVE IT ALONG, Dulcolax Pink Stool Softener, Good Neighbor Stool Softener, Harris Teeter Stool Softener, DOCUSATE SODIUM [MI], Dioctylsulphosuccinate, Sodium, exchange select stool softener, H E B Stool Softenerlaxative, MLS004773938, Quality Choice Stool Softener, DOCUSATE SODIUM [INN], Stool SoftenerRegular Strength, Topcare Stool Softenerlaxative, CVS Stool SoftenerFruit Punch, Dioctyl Sulfosuccinate, Sodium, Stool Softener Docusate Sodium, DOCUSATE SODIUM [HSDB], DOCUSATE SODIUM [USAN], DOCUSATE SODIUM 50 MG, DOCUSATE SODIUM 100 mg, Stool Softener Regular Strength, STOOL SOFTENERExtra Strength, DOCUSATE SODIUM [VANDF], GeriCare Docusate Sodium Liquid, Preferred Stool Softenerlaxative, CHEMBL1905872, CVS Health Stool Softener Clear, Kroger Stool SoftenerFruit Punch, A06AA02, Correctol Stool Softener Laxative, DOCUSATE SODIUM [WHO-DD], Non-Habit Forming Stool Softener, Sulfosuccinic acid, di-(2-ethylhexyl) ester, sodium salt, HMS3264P07, HMS3885B10, Sodium Sulfosuccinate, Diethylhexyl, Sulfosuccinate, Diethylhexyl Sodium, BCP31325, HY-B1268, Walgreens Stool SoftenerFruit Punch, EXTRA STRENGTH STOOL SOFTENER, Good Neighbor Stool Softenerlaxative, Phillips Stool SoftenerBulk Docusate, Tox21_112087, Tox21_113469, Tox21_201342, Tox21_300496, DOCUSATE SODIUM 100mg Two-Tone, Quality Choice Stool Softenerlaxative, s4588, Stool Softener LaxativeExtra Strength, DIOCTYL DISODIUM SULFOSUCCINATE, AKOS015901806, CCG-213234, CS-4813, DOCUSATE SODIUM, EXTRA STRENGTH, Docusate sodium salt, BioXtra, >=99%, Docusate Sodium-Stool Softener Laxative, Dioctyl sulfosuccinate sodium salt, 96%, DOK EXTRA STRENGTH STOOL SOFTENER, NCGC00164140-01, NCGC00254414-01, NCGC00258894-01, AS-13347, E480, SMR001595510, SY010813, Bis(2-ethylhexyl) sulfosuccinatesodium salt, Dioctyl sulfosuccinate sodium salt, >=97%, EXTRA STRENGTH STOOL SOFTENER LAXATIVE, NS00074370, STOOL SOFTENER DOCUSATE SODIUM 50 MG, DOCUSATE SODIUM, EXTRA STRENGTH250 MG, D00305, Docusate sodium salt, p.a., 99.0-100.5%, E77584, SBI-0653437.0001, Docusate sodium salt, purum, >=96.0% (TLC), Docusate sodium salt, BioUltra, >=99.0% (TLC), Docusate sodium, meets USP testing specifications, Q2815334, W-105447, F8880-5559, Sulfobutanedioic acid bis(2-ethylhexyl ester) sodium salt, Docusate sodium, British Pharmacopoeia (BP) Reference Standard, Docusate sodium, European Pharmacopoeia (EP) Reference Standard, sodium 1,4-bis(2-ethylhexyloxy)-1,4-dioxobutane-2-sulfonate, Docusate sodium, United States Pharmacopeia (USP) Reference Standard, 1,4-bis(2-ethylhexyl)sodiumsulfosuccinate pound>>Dioctyl sulfosuccinate sodium salt, Butanedioic acid, 2-sulfo-, 1,4-bis(2-ethylhexyl) ester, sodium salt (1:1), Yal
Dioctyl sodium sulfosuccinate is a widely used anionic surfactant and stool softener primarily employed to treat constipation by increasing the water and fat content in the stool, thereby facilitating easier passage.
Dioctyl sodium sulfosuccinate is the sodium salt of dioctyl sulfosuccinate and has the chemical formula C20H37NaO7S.
Dioctyl sodium sulfosuccinate appears as a white to off-white crystalline or granular powder that is soluble in water, ethanol, and glycerin.
Dioctyl sodium sulfosuccinate’s primary action involves reducing the surface tension of liquids, allowing for the more effective penetration of water and lipids into the stool, softening it and easing bowel movements.
As a gentle laxative, Dioctyl sodium sulfosuccinate is often the preferred choice for individuals needing relief from constipation without the harsh effects of stimulant laxatives.
Dioctyl sodium sulfosuccinate is widely available in over-the-counter formulations, typically in capsules, liquid, or as part of combination products that may also contain stimulant laxatives to enhance overall effectiveness.
Beyond its use as a stool softener, Dioctyl sodium sulfosuccinate has applications in the pharmaceutical industry for improving the solubility of other active pharmaceutical ingredients.
Dioctyl sodium sulfosuccinate is also used in various formulations as a dispersing agent, contributing to the uniform distribution of components in suspensions or emulsions.
Dioctyl sodium sulfosuccinate is frequently recommended for individuals who need to avoid straining during bowel movements, such as patients recovering from surgery, those with hemorrhoids, or pregnant women.
Dioctyl sodium sulfosuccinate's mild mechanism of action, when used as directed, generally results in minimal side effects, making it suitable for short-term use.
However, long-term or excessive use of Dioctyl sodium sulfosuccinate is not recommended, as it can lead to dependency or reduced bowel function.
In clinical settings, Dioctyl sodium sulfosuccinate is typically prescribed as a short-term solution to provide relief from occasional constipation or to soften stools in preparation for procedures that require clean bowels.
While generally considered safe, Dioctyl sodium sulfosuccinate's use should be monitored to avoid potential misuse or over-reliance.
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 Dioctyl sodium sulfosuccinate, 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.
Dioctyl sodium sulfosuccinate is on the World Health Organization's List of Essential Medicines.
In 2022, Dioctyl sodium sulfosuccinate 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 is a stool softener that makes bowel movements softer and easier to pass.
Docusate is used to relieve occasional constipation (irregularity).
Dioctyl sodium sulfosuccinate and senna are two different types of laxatives combined in one formula.
One is a stool softener, and one is a bowel stimulant.
Together, they can produce a bowel movement in six to twelve hours.
Dioctyl sodium sulfosuccinate prevents and treats occasional constipation.
Dioctyl sodium sulfosuccinate works by softening the stool.
Dioctyl sodium sulfosuccinate also helps the muscles in your intestines move stool.
This makes Dioctyl sodium sulfosuccinate easier to have a bowel movement.
Dioctyl sodium sulfosuccinate belongs to a group of medications called laxatives.
Dioctyl sodium sulfosuccinate is an anionic surfactant and stool softener commonly used to treat constipation by increasing the water and fat content in stools, making them easier to pass.
Chemically classified as the sodium salt of dioctyl sulfosuccinate, Dioctyl sodium sulfosuccinate has the molecular formula C20H37NaO7S and is a white to off-white crystalline or granular powder that is soluble in water, ethanol, and glycerin.
Dioctyl sodium sulfosuccinate acts as a wetting agent by reducing the surface tension of liquids, allowing water and lipids to penetrate the stool more effectively.
Dioctyl sodium sulfosuccinate is widely used in pharmaceutical formulations, often included in over-the-counter laxative products or as a complementary agent in combination with stimulant laxatives for more effective bowel evacuation.
In addition to its role in constipation management, Dioctyl sodium sulfosuccinate is employed in medical and industrial applications, such as drug formulations to enhance the solubility of active ingredients and as a dispersing agent in various formulations.
Known for its gentle mechanism of action and favorable safety profile, Dioctyl sodium sulfosuccinate is particularly suitable for patients who need to avoid straining, such as those recovering from surgery, pregnant women, or individuals with hemorrhoids.
Despite its widespread use, prolonged reliance on Dioctyl sodium sulfosuccinate is discouraged to avoid potential dependency, emphasizing its role as a short-term solution for occasional constipation.
Docusate is a medication utilized for managing and treating constipation.
Belonging to the stool softener class of drugs, Dioctyl sodium sulfosuccinate reduces the surface tension of the oil and water interface within the stool, facilitating the passage of water and lipids into the stool mass.
The goal is for the stool to become softer and move through the intestinal tract more easily.
Docusate has no indications approved by the U.S. Food and Drug Administration (FDA).
This activity aims to review the indications, mechanism of action, and contraindications of docusate in treating and managing constipation.
This activity will highlight the adverse event profile and other crucial factors of docusate, including dosing, monitoring, and relevant interactions, pertinent to interprofessional team members involved in caring for patients with constipation and related conditions.
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.
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.
Recently there has been pressure to stop prescribing docusate as it has been identified as an ineffective medicine.
Additionally, Dioctyl sodium sulfosuccinate 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.
Uses of Dioctyl Sodium Sulfosuccinate:
Dioctyl sodium sulfosuccinate is primarily used as a stool softener to relieve constipation by facilitating easier bowel movements.
Dioctyl sodium sulfosuccinate works by increasing the water and fat content in the stool, which softens it and reduces the need for straining.
This makes Dioctyl sodium sulfosuccinate particularly useful for individuals recovering from surgery, those with hemorrhoids, or pregnant women, who need to avoid excessive effort during bowel movements.
In addition to its role in constipation relief, Dioctyl sodium sulfosuccinate is often used in combination with stimulant laxatives to enhance their effectiveness and is sometimes included in preparations for medical procedures, such as colonoscopies, to ensure the bowel is clean and the stool is soft.
Dioctyl sodium sulfosuccinate's gentle action also makes it a suitable option for long-term constipation management.
Moreover, Dioctyl sodium sulfosuccinate has applications in the pharmaceutical industry, where it is used to improve the solubility of other drugs and as a dispersing agent in various formulations.
However, while Dioctyl sodium sulfosuccinate is generally considered safe for short-term use, prolonged reliance on Dioctyl sodium sulfosuccinate is discouraged to avoid potential dependency.
Constipation Relief:
Dioctyl sodium sulfosuccinate is primarily used to treat constipation by softening stools and making bowel movements easier.
Dioctyl sodium sulfosuccinate is often recommended for individuals experiencing occasional constipation or those who need gentle relief without straining.
Post-Surgery Care:
After surgery, especially abdominal or pelvic procedures, patients may need to avoid straining during bowel movements to prevent complications such as bleeding or stress on stitches.
Dioctyl sodium sulfosuccinate helps soften stools, reducing the need for excessive effort.
Hemorrhoid Relief:
Dioctyl sodium sulfosuccinate is commonly used in individuals with hemorrhoids to prevent straining, which can worsen symptoms such as pain, itching, and swelling.
Pregnancy:
Dioctyl sodium sulfosuccinate is frequently recommended for pregnant women experiencing constipation, as it is considered a safer option than stimulant laxatives, which can be harsh and cause dehydration or cramps.
Chronic Constipation Management:
Dioctyl sodium sulfosuccinate may be used as part of a long-term management strategy for chronic constipation, especially when a stool softener is needed to reduce straining.
Combination with Stimulant Laxatives:
Dioctyl sodium sulfosuccinate is sometimes combined with stimulant laxatives in over-the-counter products to help enhance the effectiveness of bowel cleansing while maintaining a softer stool.
Preparation for Medical Procedures:
In some cases, Dioctyl sodium sulfosuccinate is used in preparation for medical procedures that require the patient to have a clean colon, such as a colonoscopy, as it softens the stool for easier evacuation.
Improving Drug Solubility:
In the pharmaceutical industry, Dioctyl sodium sulfosuccinate is used as a dispersing agent to improve the solubility of certain drugs, allowing for more efficient absorption.
Enhancing the Effectiveness of Other Medications:
Dioctyl sodium sulfosuccinate is used in some formulations to enhance the efficacy of other medications, particularly those that require better solubility or dispersion in liquid form.
Medical use:
Constipation:
The main medical use of Dioctyl sodium sulfosuccinate is to treat constipation, acting as a laxative and stool softener.
In painful anorectal conditions such as hemorrhoid and anal fissures, Dioctyl sodium sulfosuccinate 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, Dioctyl sodium sulfosuccinate'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 Dioctyl sodium sulfosuccinate 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:
Dioctyl sodium sulfosuccinate, 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:
Dioctyl sodium sulfosuccinate 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 Dioctyl sodium sulfosuccinate should be ingested with plenty of water.
Interactions:
Docusate might increase the 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 constipation.
Dioctyl sodium sulfosuccinate 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 Dioctyl sodium sulfosuccinate's surfactant properties.
Perfusion studies suggest that docusate inhibits fluid absorption or stimulates secretion in the portion of the small intestine known as the jejunum.
Other uses:
Dioctyl sodium sulfosuccinate is used as a surfactant in a wide range of applications, often under the name Aerosol-OT.
Dioctyl sodium sulfosuccinate 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.
Food additive:
Dioctyl sodium sulfosuccinate has been approved by the US FDA as a "generally recognized as safe" (GRAS) additive.
Dioctyl sodium sulfosuccinate 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 Dioctyl sodium sulfosuccinate'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.
Microencapsulation:
Sodium docusate is the most widely used surfactant in reverse micelle encapsulation studies.
Non-medical brand names:
As a surfactant, Dioctyl sodium sulfosuccinate is or has been commercialized under many brand names, including DSS, 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.
Benefits of Dioctyl Sodium Sulfosuccinate:
Effective Constipation Relief:
Dioctyl sodium sulfosuccinate is a highly effective stool softener that helps relieve constipation by increasing the water content in the stool, making it easier to pass and reducing the need for straining.
Gentle Action:
Unlike stimulant laxatives, which can cause cramping and discomfort, Dioctyl sodium sulfosuccinate works gently, making it suitable for long-term use or for individuals with conditions like hemorrhoids, post-surgery recovery, or pregnancy, where straining should be avoided.
Safe for Various Populations:
Dioctyl sodium sulfosuccinate is generally safe for use by a wide range of people, including pregnant women, the elderly, and those recovering from surgery, as it is less likely to cause dehydration or electrolyte imbalances compared to other laxatives.
Prevention of Straining:
By softening the stool, Dioctyl sodium sulfosuccinate helps prevent the need to strain during bowel movements, which can be harmful for individuals with conditions like hemorrhoids, heart disease, or recent surgery.
Non-Addictive:
When used appropriately, Dioctyl sodium sulfosuccinate does not lead to dependency, unlike some stimulant laxatives, which can result in the body becoming reliant on them for bowel movements.
Suitable for Long-Term Use:
For those who suffer from chronic constipation, Dioctyl sodium sulfosuccinate provides a safer alternative for ongoing management without causing long-term harm to the digestive system, as it does not alter the natural functioning of the intestines.
Facilitates Bowel Cleansing:
Dioctyl sodium sulfosuccinate is sometimes used in medical preparations, such as before a colonoscopy, to soften the stool and make bowel cleansing more effective and comfortable.
Improves Drug Solubility:
In addition to its role in treating constipation, Dioctyl sodium sulfosuccinate is used in pharmaceutical formulations to enhance the solubility and bioavailability of active ingredients, improving the overall efficacy of the medications.
Mild on the Digestive System:
Dioctyl sodium sulfosuccinate's mild action makes it less likely to cause side effects like cramping, bloating, or discomfort, offering a more comfortable alternative to other forms of constipation relief.
Convenient Formulations:
Available in various forms such as capsules, liquid, and combination products, Dioctyl sodium sulfosuccinate is easy to incorporate into a daily routine for both occasional and regular use.
Pharmacodynamics of Dioctyl Sodium Sulfosuccinate:
Dioctyl sodium sulfosuccinate 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.
Docusate's onset of action is 6-72 hours orally and 2-15 minutes rectally.
The effects of docusate are thought to be exerted locally in the jejunum1.
Chemistry of Dioctyl Sodium Sulfosuccinate:
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.
Dioctyl sodium sulfosuccinate is a white, wax-like, plastic solid, with an odor suggestive of octyl alcohol.
Dioctyl sodium sulfosuccinate starts to decompose at about 220 °C.
The 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, 1:1 in chloroform and diethylether, and practically unlimited in petroleum ether (25 °C).
Dioctyl sodium sulfosuccinate also is highly soluble in glycerol, although this is a rather polar solvent.
Dioctyl sodium sulfosuccinate 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.
Production of Dioctyl Sodium Sulfosuccinate:
Dioctyl sodium sulfosuccinate is typically produced through the sulfonation of dioctylsuccinate or dioctyl phthalate, followed by neutralization with sodium hydroxide or sodium carbonate.
The process involves several steps:
Synthesis:
Sodium dioctyl sulfosuccinate 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−
Synthesis of Dioctyl Sulfosuccinate:
The starting material for Dioctyl sodium sulfosuccinate is dioctyl sulfosuccinate, which is prepared by reacting 2-ethylhexanol with maleic anhydride to form dioctyl maleate, followed by sulfonation using sulfur trioxide or sulfuric acid.
This reaction results in the formation of dioctyl sulfosuccinate.
Neutralization with Sodium Hydroxide:
The dioctyl sulfosuccinate is then neutralized with a sodium base, typically sodium hydroxide (NaOH) or sodium carbonate (Na₂CO₃), to form Dioctyl sodium sulfosuccinate.
The neutralization process ensures that the sulfosuccinate is converted to its sodium salt.
Purification:
After neutralization, Dioctyl sodium sulfosuccinate is purified through processes such as filtration or crystallization to remove any impurities or unreacted starting materials.
Drying and Powder Formation:
The purified Dioctyl sodium sulfosuccinate is then dried, typically under low heat, to remove any residual solvents.
The final product is usually a white to off-white crystalline powder, which can then be ground into a fine powder depending on the intended application.
Formulation:
Dioctyl sodium sulfosuccinate may then be formulated into various dosage forms, including capsules, tablets, liquid solutions, or combination products with other ingredients.
During formulation, excipients like binders, stabilizers, and preservatives may be added to enhance Dioctyl sodium sulfosuccinate's shelf life, stability, and ease of use.
Quality Control and Packaging:
Before distribution, Dioctyl sodium sulfosuccinate undergoes rigorous quality control testing to ensure it meets regulatory standards for purity, potency, and safety.
Dioctyl sodium sulfosuccinate is then packaged in appropriate containers and distributed for use in pharmaceuticals, over-the-counter products, and other applications.
History of Dioctyl Sodium Sulfosuccinate:
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.
Dioctyl sodium sulfosuccinate'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.
Handling and Storage of Dioctyl Sodium Sulfosuccinate:
Handling:
Handle Dioctyl sodium sulfosuccinate with care to avoid unnecessary exposure or inhalation of dust.
Use in well-ventilated areas to minimize inhalation risks. Avoid contact with eyes and skin.
Wear appropriate personal protective equipment (PPE), including gloves, safety goggles, and a dust mask, if necessary.
Storage:
Store Dioctyl sodium sulfosuccinate in a cool, dry, and well-ventilated area.
Keep Dioctyl sodium sulfosuccinate in tightly closed containers, away from moisture and sources of heat or direct sunlight.
Ensure containers are labeled clearly and stored in compliance with safety regulations.
Stability and Reactivity of Dioctyl Sodium Sulfosuccinate:
Stability:
Dioctyl sodium sulfosuccinate is stable under normal conditions of use and storage.
Dioctyl sodium sulfosuccinate should not degrade or react under typical storage conditions.
Ensure Dioctyl sodium sulfosuccinate remains dry to maintain its stability.
Reactivity:
Dioctyl sodium sulfosuccinate is not reactive under standard conditions.
However, Dioctyl sodium sulfosuccinate may react with strong acids or bases, and care should be taken to avoid mixing with incompatible substances.
Incompatible Materials:
Avoid contact with strong oxidizers, acids, or bases.
Hazardous Decomposition Products:
Decomposition of Dioctyl sodium sulfosuccinate under high heat or fire may produce toxic fumes, including sulfur oxides.
First Aid Measures of Dioctyl Sodium Sulfosuccinate:
Inhalation:
If inhaled, move the affected person to fresh air immediately.
If symptoms persist, seek medical attention.
Skin Contact:
In case of skin contact, wash the affected area with soap and water.
If irritation persists, seek medical advice.
Eye Contact:
If Dioctyl sodium sulfosuccinate comes into contact with eyes, rinse immediately with plenty of water for at least 15 minutes.
If irritation persists, seek medical attention.
Ingestion:
If ingested, rinse the mouth with water and seek medical attention immediately.
Do not induce vomiting unless directed by a healthcare professional.
Firefighting Measures of Dioctyl Sodium Sulfosuccinate:
Fire Hazards:
Dioctyl sodium sulfosuccinate is not highly flammable, but in case of a fire, it may release hazardous fumes, including sulfur oxides.
The material itself is not a significant fire risk under normal conditions, but care should be taken in handling to prevent exposure to heat.
Firefighting Instructions:
Use a water spray, dry chemical, or carbon dioxide (CO2) fire extinguisher to extinguish any fire.
Evacuate the area if the fire is large and use a self-contained breathing apparatus (SCBA) for respiratory protection.
Accidental Release Measures of Dioctyl Sodium Sulfosuccinate:
Personal Precautions:
In case of a spill, avoid direct contact with the substance.
Wear appropriate protective equipment, including gloves, goggles, and respiratory protection if dust is generated.
Containment and Cleanup:
Sweep up the spilled material carefully, using tools that minimize dust generation.
Place the material into an appropriate container for disposal.
Avoid releasing Dioctyl sodium sulfosuccinate into the environment.
Clean up the area with water and ensure it is properly ventilated.
Environmental Precautions:
Prevent large quantities from entering drains or water sources.
Notify local authorities if the spill poses a significant environmental risk.
Exposure Controls/Personal Protective Measures of Dioctyl Sodium Sulfosuccinate:
Occupational Exposure Limits:
There are no established exposure limits for Dioctyl sodium sulfosuccinate, but general safety guidelines for handling chemicals should be followed to minimize exposure to dust and fumes.
Engineering Controls:
Use appropriate ventilation systems to avoid inhalation of dust.
Work in a well-ventilated area, particularly when handling large quantities.
Personal Protective Equipment (PPE):
Eye Protection:
Wear safety goggles or face shields to prevent eye contact.
Skin Protection:
Wear gloves to prevent prolonged skin contact.
Respiratory Protection:
Use a dust mask or respirator if airborne particles are generated.
General Hygiene:
Wash hands thoroughly after handling the material and avoid eating or drinking in areas where the chemical is used.
Identifiers of Dioctyl Sodium Sulfosuccinate:
IUPAC name: 1,4-bis(2-ethylhexyloxy)-1,4-dioxobutane-2-sulfonic acid
CAS Number: 10041-19-7
as salt: 577-11-7
PubChem CID: 11339
as salt: 23673837
DrugBank: DB11089
as salt: DBSALT001500
ChemSpider: 10862
as salt: 10861
UNII: M7P27195AG
as salt: F05Q2T2JA0
KEGG: as salt: D00305
ChEBI: CHEBI:534
as salt: CHEBI:4674
ChEMBL: ChEMBL1477036
as salt: ChEMBL1905872
E number: E480 (thickeners, ...)
CompTox Dashboard (EPA): DTXSID8022959
ECHA InfoCard: 100.008.553
Trade names: Colace, Ex-Lax Stool Softener, others
Other names: Dioctyl sulfosuccinate
AHFS/Drugs.com: Monograph
MedlinePlus: a601113
License data:
US DailyMed: Docusate
Pregnancy
category:
AU: A
Routes of
administration: By mouth, rectal
Drug class: Stool softener
ATC code:
A06AA02 (WHO)
Legal status: CA: OTC
UK: General sales list (GSL, OTC)
US: OTC
In general: Over-the-counter (OTC)
Pharmacokinetic data
Onset of action: 12 hrs to 5 days
Duration of action: 3 days
Properties of Dioctyl Sodium Sulfosuccinate:
Formula: C20H37O7S
Molar mass: 421.57 g·mol−1
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)
SMILES: CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(O)(=O)=O
as salt: [Na+].[O-]S(=O)(=O)C(C(=O)OCC(CC)CCCC)CC(=O)OCC(CC)CCCC
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)
Key:HNSDLXPSAYFUHK-UHFFFAOYSA-N
as salt: 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
Key:APSBXTVYXVQYAB-UHFFFAOYSA-M
Molecular Weight: 444.6 g/mol
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 7
Rotatable Bond Count: 18
Exact Mass: 444.21576897 Da
Monoisotopic Mass: 444.21576897 Da
Topological Polar Surface Area: 118Ų
Heavy Atom Count: 29
Complexity: 546
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: 2
Compound Is Canonicalized: Yes
Specifications of Dioctyl Sodium Sulfosuccinate:
Appearance: White to off-white crystalline or granular powder.
Solubility: Soluble in water, ethanol, and glycerin. Insoluble in organic solvents like chloroform.
Purity: ≥ 98% pure, based on assay and content analysis.
pH (1% aqueous solution): 7.5 - 9.5.
Loss on Drying: ≤ 3% at 105°C.
Heavy Metals: ≤ 10 ppm.
Names of Dioctyl Sodium Sulfosuccinate:
Common Names:
Docusate Sodium
Sodium Dioctyl Sulfosuccinate
Dioctyl Sodium Sulfosuccinate
Colace (brand name)
DocuClean (brand name)
Softlax (brand name)