Docusate sodiumProduct ingredient for Docusate

Name
Docusate sodium
Drug Entry
Docusate

Docusate, or dioctyl sulfosuccinate, is a stool softener indicated for the treatment of constipation1. Docusate acts by increasing the amount of water the stool absorbs in the gut, making the stool softer and easier to pass 6. Docusate can be orally or rectally administered. Docusate is on the World Health Organization's List of Essential Medicines9. 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 2,5. Recently there has been pressure to stop prescribing docusate as it has been identified as an ineffective medicine3,5,8. 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.

Accession Number
DBSALT001500
Structure
Thumb
Synonyms
Dioctyl sodium sulfosuccinate / Sodium docusate
UNII
F05Q2T2JA0
CAS Number
577-11-7
Weight
Average: 444.56
Monoisotopic: 444.21576899
Chemical Formula
C20H37NaO7S
InChI Key
APSBXTVYXVQYAB-UHFFFAOYSA-M
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
IUPAC Name
sodium 1,4-bis[(2-ethylhexyl)oxy]-1,4-dioxobutane-2-sulfonate
SMILES
[Na+].CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S([O-])(=O)=O
External Links
KEGG Drug
D00305
ChemSpider
10861
ChEBI
4674
ChEMBL
CHEMBL1905872
Wikipedia
Docusate
Predicted Properties
PropertyValueSource
Water Solubility0.00306 mg/mLALOGPS
logP4.36ALOGPS
logP5.24ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)-0.75ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area109.8 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity106.23 m3·mol-1ChemAxon
Polarizability46.82 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon