Docusate

Docusate
Docusate sodium
Clinical data
Trade namesColace, Ex-Lax Stool Softener, others
Other namesDioctyl sulfosuccinate
AHFS/Drugs.comMonograph
MedlinePlusa601113
License data
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, rectal
Drug classStool softener
ATC code
Legal status
Legal status
Pharmacokinetic data
Onset of action12 hrs to 5 days[1]
Duration of action3 days[1]
Identifiers
IUPAC name
  • 1,4-bis(2-ethylhexyloxy)-1,4-dioxobutane-2-sulfonic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E numberE480 (thickeners, ...)
CompTox Dashboard (EPA)
ECHA InfoCard100.008.553
Chemical and physical data
FormulaC20H37O7S
Molar mass421.57 g·mol−1
3D model (JSmol)
Density1.1 g/cm3
Melting point153 to 157 °C (307 to 315 °F) 173-179 °C
Solubility in water1 in 70 parts mg/mL (20 °C)
SMILES
  • CCCCC(CC)COC(=O)CC(C(=O)OCC(CC)CCCC)S(O)(=O)=O

  • as salt: [Na+].[O-]S(=O)(=O)C(C(=O)OCC(CC)CCCC)CC(=O)OCC(CC)CCCC
InChI
  • InChI=1S/C20H38O7S/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)
  • Key:HNSDLXPSAYFUHK-UHFFFAOYSA-N

  • as salt: 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
  • Key:APSBXTVYXVQYAB-UHFFFAOYSA-M

Docusate is the common chemical and pharmaceutical name of the anion bis(2-ethylhexyl) sulfosuccinate, also commonly called dioctyl sulfosuccinate (DOSS).[2][3][4]

Salts of this anion, especially docusate sodium, are widely used in medicine as an emollient laxative and as stool softeners, by mouth or rectally.[1] Some studies claim that docusate is not more effective than a placebo for improving constipation.[5][6][7][8] Other docusate salts with medical use include those of calcium and potassium.[9][1][2] Docusate salts are also used as food additives, emulsifiers, dispersants, and wetting agents, among other uses.[10]

It is on the World Health Organization's List of Essential Medicines.[11] In 2022, it was the 148th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[12][13] In 2022, the combination with senna was the 261st most commonly prescribed medication in the United States, with more than 1 million prescriptions.[12][14]

  1. ^ a b c d "Docusate Salts". The American Society of Health-System Pharmacists. Archived from the original on 23 September 2015. Retrieved 11 August 2015.
  2. ^ a b American Society of Health-System Pharmacists (15 August 2011). "Stool Softeners". Archived from the original on 5 September 2015.
  3. ^ Cite error: The named reference cary1937 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference wils1955 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Fakheri2019 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference CADTH2014 was invoked but never defined (see the help page).
  7. ^ Candy B, Jones L, Larkin PJ, Vickerstaff V, Tookman A, Stone P (May 2015). "Laxatives for the management of constipation in people receiving palliative care" (PDF). The Cochrane Database of Systematic Reviews. 13 (5): CD003448. doi:10.1002/14651858.CD003448.pub4. PMC 6956627. PMID 25967924.
  8. ^ Ramkumar D, Rao SS (April 2005). "Efficacy and safety of traditional medical therapies for chronic constipation: systematic review". The American Journal of Gastroenterology. 100 (4): 936–71. doi:10.1111/j.1572-0241.2005.40925.x. PMID 15784043. S2CID 13869933.
  9. ^ Cite error: The named reference Nurse2013 was invoked but never defined (see the help page).
  10. ^ Ash M, Ash I (2004). Handbook of preservatives. Endicott, N.Y.: Synapse information resources. p. 375. ISBN 9781890595661.
  11. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  12. ^ a b "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  13. ^ "Docusate Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  14. ^ "Senna; Docusate Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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