Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameSodium Tetradecyl Sulfate
Accession NumberDB00464  (APRD00575)
Typesmall molecule
Groupsapproved
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
STSNot AvailableNot Available
Tetradecyl sodium sulfateNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
Fibro-VeinNot Available
SotradecolNot Available
Brand mixturesNot Available
Categories
CAS number1191-50-0
WeightAverage: 294.451
Monoisotopic: 294.186480138
Chemical FormulaC14H30O4S
InChI KeyInChIKey=URLJMZWTXZTZRR-UHFFFAOYSA-N
InChI
InChI=1S/C14H30O4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-19(15,16)17/h2-14H2,1H3,(H,15,16,17)
IUPAC Name
(tetradecyloxy)sulfonic acid
SMILES
CCCCCCCCCCCCCCOS(O)(=O)=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassOrganic Sulfuric Acids and Derivatives
SubclassSulfuric Acid Monoesters
Direct parentSulfuric Acid Monoesters
Alternative parentsPolyamines
Substituentspolyamine
Classification descriptionThis compound belongs to the sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group.
Pharmacology
IndicationFor the treatment of small uncomplicated varicose veins of the lower extremities that show simple dilation with competent valves.
PharmacodynamicsSodium tetradecyl sulfate is an anionic surfactant which occurs as a white, waxy solid. It is used as a sclerosing agent in sclerotherapy. Sclerotherapy is an injection of a sclerosing agent directly through the skin into a lesion and is used primarily for slow-flow vascular anomalies, particularly for venous malformation and lymphatic malformation. Intravenous injection causes intima inflammation and thrombus formation. This usually occludes the injected vein. Subsequent formation of fibrous tissue results in partial or complete vein obliteration that may or may not be permanent.
Mechanism of actionSodium tetradecyl sulfate is a potent toxin for endothelial cells in that brief exposure to even low concentrations are effective in stripping endothelium over a considerable distance and exposing highly thrombogenic endothelium in the process. Diluted sodium tetradecyl sulfate is also able to induce a hypercoagulable state, possibly by selective inhibition of protein C, and can also promote platelet aggregation.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=1250 mg/kg (Orally in rat); LD50=3 ml/kg (Skin in rat)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9406
Blood Brain Barrier + 0.9525
Caco-2 permeable - 0.6012
P-glycoprotein substrate Non-substrate 0.7254
P-glycoprotein inhibitor I Non-inhibitor 0.7654
P-glycoprotein inhibitor II Non-inhibitor 0.9757
Renal organic cation transporter Non-inhibitor 0.9101
CYP450 2C9 substrate Non-substrate 0.8409
CYP450 2D6 substrate Non-substrate 0.8488
CYP450 3A4 substrate Non-substrate 0.5649
CYP450 1A2 substrate Non-inhibitor 0.8415
CYP450 2C9 substrate Non-inhibitor 0.8494
CYP450 2D6 substrate Non-inhibitor 0.9019
CYP450 2C19 substrate Non-inhibitor 0.8269
CYP450 3A4 substrate Non-inhibitor 0.9805
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.926
Ames test Non AMES toxic 0.9133
Carcinogenicity Carcinogens 0.6724
Biodegradation Ready biodegradable 0.7562
Rat acute toxicity 2.2812 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6277
hERG inhibition (predictor II) Non-inhibitor 0.6966
Pharmacoeconomics
Manufacturers
  • Bioniche pharma usa llc
  • Elkins sinn div ah robins co inc
Packagers
Dosage forms
FormRouteStrength
SolutionIntravenous
Prices
Unit descriptionCostUnit
Sotradecol 3% vial33.0USDml
Sotradecol 1% vial19.68USDml
Tromboject 3 %3.77USDml
Tromboject 1 %3.46USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility2.62e-03 g/lALOGPS
logP2.59ALOGPS
logP5.31ChemAxon
logS-5ALOGPS
pKa (strongest acidic)-1.5ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area63.6ChemAxon
rotatable bond count14ChemAxon
refractivity78.14ChemAxon
polarizability35.74ChemAxon
number of rings0ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound5248
PubChem Substance46505919
ChemSpider5058
Therapeutic Targets DatabaseDAP001276
PharmGKBPA164746759
Drug Product Database363332
RxListhttp://www.rxlist.com/cgi/generic2/sotradecol.htm
Drugs.comhttp://www.drugs.com/cdi/sodium-tetradecyl-sulfate.html
ATC CodesC05BB04
AHFS Codes
  • 24:16.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(52.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Vitamin K-dependent protein C

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Vitamin K-dependent protein C P04070 Details

References:

  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  2. Jacobson BF, Franz RC, Hurly EM, Norman GL, Becker P, Myburgh JA, Mendelow BV: Mechanism of thrombosis caused by sclerotherapy of esophageal varices using sodium tetradecyl sulphate. Surg Endosc. 1992 Jan-Feb;6(1):4-9. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  4. Parsi K, Exner T, Low J, Ma DD, Joseph JE: In vitro effects of detergent sclerosants on antithrombotic mechanisms. Eur J Vasc Endovasc Surg. 2009 Aug;38(2):220-8. Epub 2009 May 12. Pubmed

2. Vitamin K-dependent protein S

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Vitamin K-dependent protein S P07225 Details

References:

  1. Parsi K, Exner T, Low J, Ma DD, Joseph JE: In vitro effects of detergent sclerosants on antithrombotic mechanisms. Eur J Vasc Endovasc Surg. 2009 Aug;38(2):220-8. Epub 2009 May 12. Pubmed
  2. Jacobson BF, Franz RC, Hurly EM, Norman GL, Becker P, Myburgh JA, Mendelow BV: Mechanism of thrombosis caused by sclerotherapy of esophageal varices using sodium tetradecyl sulphate. Surg Endosc. 1992 Jan-Feb;6(1):4-9. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10