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Home > Encyclopedia > Dioctyl sulfosuccinate

Dioctyl sulfosuccinate

Dioctyl sulfosuccinate structure

Dioctyl sulfosuccinate 

structure
  • CAS No:

    10041-19-7

  • Formula:

    C20H38O7S

  • Chemical Name:

    Dioctyl sulfosuccinate

  • Synonyms:

    Butanedioic acid,2-sulfo-,1,4-bis(2-ethylhexyl) ester;Succinic acid,sulfo-,1,4-bis(2-ethylhexyl) ester;Butanedioic acid,sulfo-,1,4-bis(2-ethylhexyl) ester;Succinic acid,sulfo-,bis(2-ethylhexyl) ester;Bis(2-ethylhexyl) sulfosuccinate;Sulfosuccinic acid bis(2-ethylhexyl) ester;Spolion 8;Dioctyl sulfosuccinate;Di(2-ethylhexyl) sulfosuccinate;1,4-Bis(2-ethylhexyl) 2-sulfosuccinate;Docusate;Dioctyl sulfosuccinic acid;Diocto;Lumiten ID-S 3525;Imbirol OD;DO 113;147-89-7;21954-86-9;123344-03-6;732239-99-5;894411-97-3;1878156-38-7;2019157-28-7;2170442-06-3;2222995-18-6

  • Categories:

    Surfactant  >  Anionic Surfactants

Description

1,4-bis(2-ethylhexyl) sulfosuccinate is a diester and an organosulfonic acid.|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, it 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.|Docusate is an orally available, over-the-counter laxative and stool softener used to treat or prevent constipation. Docusate has not been linked to serum enzyme elevations during therapy or to clinically apparent liver injury with jaundice.|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.

Dioctyl sulfosuccinate Basic Attributes

422.57652

422.58

233-124-0

M7P27195AG

DTXSID1044279

2914509090

Characteristics

115.35000

5.23290

1.096±0.06 g/cm3(Predicted)

153-157

566.6°C at 760 mmHg

296.5°C

Soluble

2.56E-14mmHg at 25°C

Toxicity

Docusate is not known to be carcinogenic or cause reproductive toxicity. It was not mutagenic in the Ames assay [MSDS]. Acute oral LD50 in rat is 1900 mg/kg [MSDS].

Docusate has not been linked to elevations in serum enzyme levels during treatment, although there have been few published studies of its effects of liver tests. There have been no cases of clinically apparent liver injury attributable to docusate published in the literature and, thus, significant liver injury from docusate must be exceedingly rare, if it occurs at all.

Drug Information

Indicated for the treatment of constipation associated with dry, hard stools or opioid induced constipation. Though recently, pressure has been building to end the use of docusate over concerns of efficacy.

Docusate is an orally available, over-the-counter laxative and stool softener used to treat or prevent constipation. Docusate has not been linked to serum enzyme elevations during therapy or to clinically apparent liver injury with jaundice.

Gastrointestinal Agents

Docusate sodium 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 jejunum.

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)

Docusate is not absorbed systemically. As the actions of docusate are local and it is not absorbed, the pharmacokinetic parameters are not available.|If docusate is systemically absorbed, it undergoes biliary excretion.

Recent studies suggest that docusate's mechanism of action is due largely to it's surfactant effect in the intestines, which allow fat and water into the feces to soften the stool. Docusate’s mechanism of action was investigated in 1985 on healthy patients. Docusate was added directly to the jejunum based on calculated concentrations of docusate in the jejunum. At this concentration, there was an increase in secretion of water, sodium, chloride, and potassium as well as a decrease in absorption of glucose and bicarbonate. Based on in vitro data, the authors suggested this effect was due to an increase in intracellular cyclic AMP either directly through docusate or E series prostaglandins.

Aerosol OT

Dioctyl sulfosuccinate Use and Manufacturing

Uses

Stool softener.Docusate, or dioctyl sulfosuccinate, or 1,4-bis(2-ethylhexyl) 2-sulphosuccinate 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, it 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.

Butanedioic acid, 2-sulfo-, 1,4-bis(2-ethylhexyl) ester: ACTIVE

Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]

Computed Properties

Molecular Weight:422.6
XLogP3:5.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:18
Exact Mass:422.23382472
Monoisotopic Mass:422.23382472
Topological Polar Surface Area:115
Heavy Atom Count:28
Complexity:539
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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