Sodium tetradecyl sulfate

Sodium tetradecyl sulfate
Names
Other names7-Ethyl-2-methyl-4-hendecanol sulfate sodium salt
IUPAC name
  • Sodium 7-ethyl-2-methyl-4-undecanyl sulfate
Clinical data
Main usesVaricose veins, esophageal varices, spider veins[1][2]
Side effectsPain, redness, swelling, increased pigmentation, skin breakdown[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		Intravenous injection
External links
AHFS/Drugs.comMonograph
Legal
Legal status
  • In general: ℞ (Prescription only)
Chemical and physical data
FormulaC14H29NaO4S
Molar mass316.43 g·mol−1
3D model (JSmol)
SMILES
  • CCCCC(CC)CCC(CC(C)C)OS(=O)(=O)[O-].[Na+]
InChI
  • 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

Sodium tetradecyl sulfate (STS), sold under the brand name Sotradecol, is a medication used to treat varicose veins, esophageal varices, and spider veins.[1][2] It is used during a procedure known as sclerotherapy by injection into a vein.[2]

Common side effects include pain, redness, swelling, increased pigmentation, and skin breakdown.[1] Serious side effects may include pulmonary embolism, stroke, and anaphylaxis.[1] It is an anionic surfactant and detergent which results in inflammation, blood clot formation, and scarring of the vein into which it is injected.[2]

Sodium tetradecyl sulfate was approved for medical use in the United States in 1946.[2] It is relatively low in cost.[1] In the United States 5 doses costs about 330 USD as of 2021.[3] In the United Kingdom this amount costs the NHS about £34.[4]

Medical uses

It is occasionally used for the treatment of stabilisation of joints that regularly dislocate, particularly in patients with Ehlers-Danlos syndrome.[5]

Dosage

Up to 2 mL may be given at easy site of injection.[2] A small initial dose is recommended before further doses to rule out a significant reaction.[2]

In the UK, Ireland, Italy, Australia, New Zealand and South Africa, it is sold in concentrations of 0.2%, 0.5%, 1.0%, and 3%.[6]

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. 1 2 3 4 5 6 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.
  2. 1 2 3 4 5 6 7 "Sodium Tetradecyl Sulfate Monograph for Professionals". Drugs.com. Retrieved 14 October 2021.
  3. ↑ "Sodium tetradecyl sulfate Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 19 January 2021. Retrieved 14 October 2021.
  4. ↑ BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 248. ISBN 978-0-85711-369-6.
  5. ↑ 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.
  6. ↑ "Fibro-Vein history and details". Archived from the original on 20 May 2013. Retrieved 22 November 2021.
Identifiers:
This article is issued from Offline. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.