Sodium tetradecyl sulfate

Sodium tetradecyl sulfate (STS) is a commonly used synonym for 7-ethyl-2-methyl-4-undecanyl sulfate sodium salt[1] which is anionic surfactant that is the active component of the sclerosant drug Sotradecol. It is commonly used in the treatment of varicose and spider veins of the leg, during the procedure of sclerotherapy.[2] Being a detergent, its action is on the lipid molecules in the cells of the vein wall, causing inflammatory destruction of the internal lining of the vein and thrombus formation eventually leading to sclerosis of the vein. It is used in concentrations ranging from 0.1% to 3% for this purpose. It is occasionally used for the treatment of stabilisation of joints that regularly dislocate, particularly in patients with Ehlers-Danlos syndrome.[3] In the UK, Ireland, Italy, Australia, New Zealand and South Africa, it is sold under the trade-name Fibro-Vein in concentrations of 0.2%, 0.5%, 1.0%, and 3%.[4]

Sodium tetradecyl sulfate
Clinical data
Other names7-Ethyl-2-methyl-4-hendecanol sulfate sodium salt
AHFS/Drugs.comConsumer Drug Information
Routes of
administration		Intravenous injection
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • Sodium 7-ethyl-2-methyl-4-undecanyl sulfate
CAS Number
  • 139-88-8 N
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.892
Chemical and physical data
FormulaC14H29NaO4S
Molar mass316.43 g·mol−1
3D model (JSmol)
  • CCCCC(CC)CCC(CC(C)C)OS(=O)(=O)[O-].[Na+]
  • InChI=1S/C14H30O4S.Na/c1-5-7-8-13(6-2)9-10-14(11-12(3)4)18-19(15,16)17;/h12-14H,5-11H2,1-4H3,(H,15,16,17);/q;+1/p-1 N
  • Key:FVEFRICMTUKAML-UHFFFAOYSA-M N
 NY (what is this?)  (verify)

Synthesis

It may be prepared by the aldol condensation of methyl isobutyl ketone and 2-ethylhexanal (which is itself formed by the aldol self-concensation of butyraldehyde), followed by sulfonation of the resulting alcohol.

References
  1. "SOTRADECOL® (Sodium tetradecyl sulfate)" (PDF). Retrieved 29 August 2014.
  2. Jenkinson HA, Wilmas KM, Silapunt S (November 2017). "Sodium Tetradecyl Sulfate: A Review of Clinical Uses". Dermatologic Surgery. 43 (11): 1313–1320. doi:10.1097/DSS.0000000000001143. PMID 28430735.
  3. Burling F (2019). "Comparison of tetradecyl sulfate versus polidocanol injections for stabilisation of joints that regularly dislocate in an Ehlers-Danlos population". BMJ Open Sport & Exercise Medicine. 5 (1): e000481. doi:10.1136/bmjsem-2018-000481. PMC 6350757. PMID 30792884.
  4. Fibro-Vein history and details
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.