Sotradecol

Sodium tetradecyl sulfate

cas 139-88-8, Na FORM

free form  300-52-7

• Molecular FormulaC₁₄H₂₉NaO₄S
• Average mass316.432 Da

139-88-8 [RN], cas 1191-50-0,

• CAS No.68043-79-8

4-Undecanol, 7-ethyl-2-methyl-, hydrogen sulfate, sodium salt (1:1)
7-Ethyl-2-methyl-4-undecyl sulfate sodium salt
UNII:Q1SUG5KBD6
натрия тетрадецилсульфат [Russian] [INN]
تتراديسيل سولفات صوديوم [Arabic] [INN]
十四烷硫酸钠 [Chinese] [INN]
CAS Registry Number: 139-88-8 
CAS Name: 7-Ethyl-2-methyl-4-undecanol hydrogen sulfate sodium salt 
Additional Names: 7-ethyl-2-methyl-4-hendecanol sulfate sodium salt; sodium 2-methyl-7-ethyl-4-undecyl sulfate; sodium 7-ethyl-2-methylundecyl-4-sulfate 
Trademarks: Sotradecol (Elkins-Sinn); Tergitol 4; Trombavar; Trombovar 
Molecular Formula: C14H29NaSO4, Molecular Weight: 316.43 
Percent Composition: C 53.14%, H 9.24%, Na 7.27%, S 10.13%, O 20.22% 
Properties: White, waxy solid. Sol in water, alcohol, ether. The pH of a 5% soln is from 6.5 to 9.0. Surface tension (dynes/cm) of aq soln at 25°: 56.5 dynes/cm (0.05% w/w); 52 (0.10%); 47 (0.20%); 40 (0.50%); 35 (1.0%). LD50 orally in rats: 4.95 g/kg, H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol.30, 63 (1948). 
Toxicity data: LD50 orally in rats: 4.95 g/kg, H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol.30, 63 (1948) 
Use: Wetting agent. 
Therap-Cat: Sclerosing agent., Keywords: Sclerosing Agent.

Synonyms of Sodium Tetradecyl Sulfate [INN]

• 4-Ethyl-1-isobutyloktylsiran sodny
• EINECS 205-380-3
• Natrii tetracylis sulfas
• Natrii tetradecylis sulfas
• Natrii tetradecylis sulfas [Latin]
• Natrii tetradecylsulfas
• NSC 755887
• Obliterol
• Sodium sotradecol
• Sodium tetradecyl sulfate
• Sotradecol
• Tergitol
• Tergitol 4
• Tergitol anionic 4
• Tergitol penetrant 4
• Tetradecilsulfato sodico
• Tetradecilsulfato sodico [Spanish]
• Tetradecyl sulfate de sodium
• Trombovar
• UNII-Q1SUG5KBD6
• Varicol

An anionic surface-active agent used for its wetting properties in industry and used in medicine as an irritant and sclerosing agent for hemorrhoids and varicose veins.

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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

Compound name:	Sodium Tetradecyl Sulfate
Spectrum type:	1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)

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

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
showIUPAC 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
showSMILES
showInChI
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///////Sodium tetradecyl sulfate, sotradecol, Sclerosing Agent, varicose veins

CCCCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]