Docusate sodium
Overview
Description
Docusate sodium, also known as dioctyl sodium sulfosuccinate, is a widely used compound in the medical field, primarily as a stool softener. It is an anionic surfactant that helps to increase the amount of water the stool absorbs in the gut, making the stool softer and easier to pass. This compound is commonly used to treat constipation and is available in various forms, including oral and rectal administration .
Scientific Research Applications
Docusate sodium has a wide range of applications in scientific research, including:
Mechanism of Action
Target of Action
Docusate sodium, also known as dioctyl sulfosuccinate, is primarily targeted at the gastrointestinal tract . It acts on the stool within the gut, which is the primary target of its action .
Mode of Action
This compound is an anionic surfactant . It works by reducing the surface tension of the stool, which allows more intestinal water and fats to combine with the stool . This process results in a softer fecal mass . The compound’s interaction with its target leads to an increase in the amount of water the stool absorbs in the gut, making the stool softer and easier to pass .
Biochemical Pathways
It is known that the compound’s surfactant effect in the intestines allows fat and water into the feces to soften the stool .
Pharmacokinetics
This compound exerts its clinical effect in the gastrointestinal tract . There is some evidence that this compound is absorbed and is excreted in the bile . It is also capable of enhancing the absorption of certain compounds administered concomitantly . The onset of action of this compound is 6-72 hours orally and 2-15 minutes rectally .
Result of Action
The primary molecular and cellular effect of this compound’s action is the softening of the stool. This is achieved by increasing the amount of water the stool absorbs in the gut . This effect decreases the strain and discomfort associated with constipation .
Safety and Hazards
Biochemical Analysis
Biochemical Properties
Docusate Sodium acts as a surfactant laxative, promoting the incorporation of water and fats into the stool through a reduction in surface tension, resulting in a softer fecal mass . This biochemical property allows this compound to interact with the biomolecules within the gastrointestinal tract, particularly the water and lipid components of the stool .
Cellular Effects
This compound exerts its effects on the cells lining the gastrointestinal tract. It increases the secretion of water, sodium, chloride, and potassium, while decreasing the absorption of glucose and bicarbonate . This results in a softer stool that is easier to pass, thereby alleviating constipation .
Molecular Mechanism
The molecular mechanism of this compound involves its surfactant effect in the intestines, which allows fat and water into the feces to soften the stool . This is achieved by reducing the surface tension at the oil-water interface within the stool, thereby facilitating the incorporation of water and lipids into the stool mass .
Temporal Effects in Laboratory Settings
The onset of action of this compound is between 6-72 hours when administered orally, and between 2-15 minutes when administered rectally . The effectiveness of this compound in treating constipation remains unclear, as several studies report it to be no more effective than a placebo for increasing the frequency of stool or stool softening .
Dosage Effects in Animal Models
While this compound is generally considered safe for use in animals, there are potential side effects that pet owners should be aware of. These can include diarrhea, vomiting, abdominal pain, and dehydration . When administered at 3–5 times the recommended dosage, this compound has been reported to produce severe diarrhea, rapid dehydration, and death in horses .
Metabolic Pathways
This compound is metabolized in the liver, where it undergoes significant first-pass metabolism, forming both active and inactive metabolites . Although this compound undergoes hepatic metabolism and has high plasma protein binding, there have been no reports of clinically apparent hepatotoxicity .
Subcellular Localization
Given its function as a stool softener and its mechanism of action, it is likely that this compound primarily localizes within the gastrointestinal tract where it exerts its effects .
Preparation Methods
Synthetic Routes and Reaction Conditions: Docusate sodium is synthesized through the esterification of sulfosuccinic acid with 2-ethylhexanol, followed by neutralization with sodium hydroxide. The reaction typically involves heating the reactants under reflux conditions to facilitate the esterification process. The resulting product is then purified through distillation or recrystallization to obtain this compound in its pure form .
Industrial Production Methods: In industrial settings, this compound is produced on a larger scale using similar synthetic routes. The process involves the continuous esterification of sulfosuccinic acid with 2-ethylhexanol in the presence of a catalyst, followed by neutralization with sodium hydroxide. The product is then subjected to various purification steps, including filtration, distillation, and drying, to achieve the desired purity and quality .
Chemical Reactions Analysis
Types of Reactions: Docusate sodium primarily undergoes hydrolysis and oxidation reactions. In the presence of strong acids or bases, it can hydrolyze to form sulfosuccinic acid and 2-ethylhexanol. Additionally, it can undergo oxidation reactions, especially when exposed to strong oxidizing agents .
Common Reagents and Conditions:
Hydrolysis: Strong acids (e.g., hydrochloric acid) or bases (e.g., sodium hydroxide) under reflux conditions.
Oxidation: Strong oxidizing agents (e.g., potassium permanganate) under controlled temperature and pH conditions.
Major Products Formed:
Hydrolysis: Sulfosuccinic acid and 2-ethylhexanol.
Oxidation: Various oxidized derivatives of this compound, depending on the specific conditions and reagents used.
Comparison with Similar Compounds
Polyethylene glycol 3350: Another commonly used laxative that works by retaining water in the stool, resulting in softer stools and easier bowel movements.
Lactulose: A synthetic sugar used to treat constipation by drawing water into the bowel, softening the stool.
Magnesium hydroxide: An osmotic laxative that increases water in the intestines, promoting bowel movements.
Uniqueness of Docusate Sodium: this compound is unique in its dual role as a stool softener and an anionic surfactant. Unlike other laxatives that primarily work by osmosis or increasing bowel motility, this compound specifically reduces the surface tension of stools, facilitating the incorporation of water and fats. This unique mechanism makes it particularly effective for patients who need to avoid straining during bowel movements .
Properties
IUPAC Name |
sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
APSBXTVYXVQYAB-UHFFFAOYSA-M |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(=O)(=O)[O-].[Na+] |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C20H37NaO7S |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
10041-19-7 (Parent) |
Source
|
| Record name | Docusate sodium [USAN:USP:INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000577117 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID8022959 |
Source
|
| Record name | Docusate sodium | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID8022959 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
444.6 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Commercially available in rolls of very thin wax-like solid; as solution (50-75%) in various solvents; [Merck Index] White waxy solid; [MSDSonline] |
Source
|
| Record name | Docusate sodium | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
| URL | https://haz-map.com/Agents/3967 | |
| Description | Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents. | |
| Explanation | Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission. | |
Solubility |
SOL IN WATER (G/L): 15 (25 °C), 23 (40 °C), 30 (50 °C), 55 (70 °C); SOL IN CARBON TETRACHLORIDE, PETROLEUM ETHER, NAPHTHA, XYLENE, DIBUTYL PHTHALATE, LIQUID PETROLATUM, ACETONE, ALCOHOL, VEGETABLE OILS; VERY SOL IN WATER-MISCIBLE ORGANIC SOLVENTS, FREELY SOL IN GLYCERIN, Water Solubility = 71000 mg/L @ 25 °C |
Source
|
| Record name | BIS(2-ETHYLHEXYL) SODIUM SULFOSUCCINATE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3065 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Mechanism of Action |
In vitro studies suggest that these salts of dioctylsulfosuccinic acid lower the surface tension of the stool to permit water and lipids to enter more readily and thus soften the feces. ... More recent evidence indicates that they may stimulate the secretion of water and electrolytes on contact with the mucosa., Reduce surface film tension of interfacing liquid contents of the bowel, promoting permeation of additional liquid into the stool to form a softer mass. /Laxatives/ |
Source
|
| Record name | BIS(2-ETHYLHEXYL) SODIUM SULFOSUCCINATE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3065 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
WHITE, WAX-LIKE SOLID | |
CAS No. |
577-11-7 |
Source
|
| Record name | Docusate sodium [USAN:USP:INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000577117 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Docusate sodium | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID8022959 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Docusate sodium | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.008.553 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | DOCUSATE SODIUM | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/F05Q2T2JA0 | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| Record name | BIS(2-ETHYLHEXYL) SODIUM SULFOSUCCINATE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3065 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
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