Basic information
- CAS
10041-19-7- Standard SMILES
CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(=O)(=O)O- InChIKey
HNSDLXPSAYFUHK-UHFFFAOYSA-N- Molecular formula
- C20H38O7S
- Average molar mass
- 422.6 g/mol
- Monoisotopic mass
- 422.23382456
Overview
1,4-bis(2-ethylhexyl) sulfosuccinate is an organosulfonic acid and a diester.
Names & identifiers
- Preferred name
- Docusate
- IUPAC
- 1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonic acid
- English name
- 1,4-bis(2-ethylhexyl) 2-sulphosuccinate
- Molecular formula
- C20H38O7S
- Molecular weight
- 422.58
Names & synonyms
Show more names
Database identifiers
- CAS
10041-19-7- PubChem CID
- 11339
- DTXSID
DTXSID1044279- ChEMBL
CHEMBL1477036- ChEBI
CHEBI:534- UNII
- M7P27195AG
- EC Number
- 233-124-0
- Nikkaji
- J8.977J
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 18
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 539
Experimental & physicochemical properties
Chemical Classes
Other Uses -> Emulsifiers/Surfactants
Industrial compound
Physicochemical properties
- Density
- 1.096 · 1.096±0.06 g/cm3(Predicted)
- pka
- 0.08 · 0.08±0.50(Predicted)
- FDA UNII
- 7 P27195AG · M7P27195AG
- EPA Substance Registry System
- 1 · Butanedioic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester (10041-19-7)
- TSCA
- TSCA listed
Safety & regulation
Hazard information
Toxicology
Hepatotoxicity
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.
Adverse Effects
The adverse effects of docusate are generally mild. Anorexia, diarrhea, and vomiting are usually associated with excess doses of docusate medication. Some people may experience abdominal cramping or, rarely, develop a rash as adverse reactions to docusate.
Toxicity Summary
Docusate has a well-documented safety and tolerability profile and has been in use in the United States since the 1950s. Animal studies have demonstrated that docusate sodium ear drops can cause significant ototoxicity. Therefore, docusate ear drops should be avoided in patients with tympanic membrane perforation.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Docusate
DILI Negative
oral
DOI:10.1016/j.drudis.2019.09.022
Safety data
- tsca
- TSCA listed
Chemistry & industry
Pharmacology
Pharmacodynamics
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.
Mechanism of Action
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.
MeSH Pharmacological Classification
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.
Absorption, Distribution and Excretion
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.
Uses & manufacturing
Uses
Surfactant, wetting agent, and solubilizer used in drugs, cosmetics, and foods; Has been used as a laxative and cerumenolytic; [ChemIDplus]
Use (kg; approx.) in Germany (2009): >100
Applications
UsesStool softener.
Suppliers1 total
Additional notes
DefinitionChEBI: 1,4-bis(2-ethylhexyl) sulfosuccinate is a diester and an organosulfonic acid.
Related reactions
Compound notes
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