Sotradecol, Sodium tetradecyl sulfate

Sodium tetradecyl sulfate is an anionic surfactant which occurs as a white, waxy solid. The structural formula is as follows:

C₁₄H₂₈NaS0₄       7-Ethyl -2-methyl -4-hendecanol sulfate sodium salt       MW 316.44Sotradecol® (sodium tetradecyl sulfate injection) is a sterile nonpyrogenic solution for intravenous use as a sclerosing agent.

1% (10 mg/mL): Each mL contains sodium tetradecyl sulfate 10 mg, benzyl alcohol 0.02 mL and dibasic sodium phosphate, anhydrous 4.0 mg in Water for Injection. pH 7.9; monobasic sodium phosphate and/or sodium hydroxide added, if needed, for pH adjustment.

3% (30 mg/mL): Each mL contains sodium tetradecyl sulfate 30 mg, benzyl alcohol 0.02 mL and dibasic sodium phosphate, anhydrous 9.0 mg in Water for Injection. pH 7.9; monobasic sodium phosphate and/or sodium hydroxide added, if needed, for pH adjustment.

Sodium tetradecyl sulfate (STS) is a commonly used synonym for 7-ethyl-2-methyl-4-undecanyl sulfate sodium salt^[1] which is anionicsurfactant 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]

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.

SYN

RSC Advances, 10(22), 12788-12799; 2020

https://pubs.rsc.org/en/content/articlelanding/2020/RA/D0RA00386G

PAT

CN 106278961

CN 106278958

 U.S.S.R., 1051067,

NMR

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

Sodium tetradecyl sulfate

Clinical data
Other names	7-Ethyl-2-methyl-4-hendecanol sulfate sodium salt
AHFS/Drugs.com	Consumer Drug Information
Routes of administration	Intravenous injection
ATC code	C05BB04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
show IUPAC name
CAS Number	139-88-8
PubChemCID	14492
ChemSpider	8440
UNII	Q1SUG5KBD6
ChEMBL	ChEMBL1200354
CompTox Dashboard (EPA)	DTXSID3041530
ECHA InfoCard	100.004.892
Chemical and physical data
Formula	C14H29NaO4S
Molar mass	316.43 g·mol−1
3D model (JSmol)	Interactive image
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