Docusate

HCID 11339

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

DOCUSATEDocusate hydrogen10041-19-7Spolion 8DioctoDioctylsulfosuccinsaeureDocusatesDIOCTYLSULFOSUCCINATEM7P27195AGDTXSID1044279Butanedioic acid, 2-sulfo-, 1,4-bis(2-ethylhexyl) ester1,4-Bis(2-ethylhexyloxy)-1,4-dioxo-2-butansulfonsaeure [IUPAC]
Show more names
Dioctyl Sulfosuccinic AcidBis(2-ethylhexyl)sulfosuccinateBIS(2-ETHYLHEXYL)SULPHOSUCCINATE1,4-bis(2-ethylhexyl) 2-sulphosuccinateSULPHOSUCCINICACID,BIS(2-ETHYLHEXYL)ESTERSulfosuccinic acid 1,4-bis(2-ethylhexyl) esterButanedioic acid,sulfo-,1,4-bis(2-ethylhexyl)esterButanedioic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester
1,4-Bis(2-ethylhexyloxy)-1,4-dioxo-2-butansulfonsaeure (IUPAC)DocQLaceSulfosuccinate, DioctylRefChem:55059DTXCID90242791,4-bis(2-ethylhexoxy)-1-oxo-4-oxoniumylidenebutane-2-sulfonate233-124-0DIOCTYL SULFOSUCCINATE

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

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Uses -> Emulsifiers/Surfactants

Industrial compound

DrugsPharmaceuticals
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]
SolubilitySoluble
Human DrugsBreast Feeding; Lactation; Milk, Human; Gastrointestinal Agents; Laxatives; Surface-Active Agents
Melting Point153-157

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

Regulatory InformationChemical: Butanedioic acid, sulfo-, 1,4-bis(2-ethylhexyl) ester
Hazards SummaryNo evidence of teratogenicity in rats or humans; One case report of hypomagnesemia associated with maternal excessive/chronic use of laxatives by the mother; [REPROTOX] See Docusate sodium.

Toxicology

Hepatotoxicity · 1 item

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 · 1 item

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 · 1 item

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 · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Docusate

DILI Negative

oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

tsca
TSCA listed

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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 · 1 item

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 · 1 item

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 · 2 items

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 · 2 items

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

General Manufacturing InformationButanedioic acid, 2-sulfo-, 1,4-bis(2-ethylhexyl) ester: ACTIVE

Applications

UsesStool softener.

Suppliers1 total

陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

Additional notes

DefinitionChEBI: 1,4-bis(2-ethylhexyl) sulfosuccinate is a diester and an organosulfonic acid.

Related reactions

2 records

Compound notes

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