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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
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sotradecolinjection, solution10 mg/mLintravenousAngiodynamics2004-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sotradecolinjection, solution30 mg/mLintravenousAngiodynamics2004-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sotradecolinjection, solution10 mg/mLintravenousMylan Institutional LLC2013-04-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sotradecolinjection, solution30 mg/mLintravenousMylan Institutional LLC2013-04-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
Fibro-VeinNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number1191-50-0
WeightAverage: 294.451
Monoisotopic: 294.186480138
Chemical FormulaC14H30O4S
InChI KeyURLJMZWTXZTZRR-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfuric acid monoesters. These are organic compounds containing the sulfuric acid monoester functional group, with the generic structure ROS(O)(=O)=O, (R=organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassSulfuric acid esters
Direct ParentSulfuric acid monoesters
Alternative Parents
Substituents
  • Sulfuric acid monoester
  • Alkyl sulfate
  • Sulfate-ester
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9406
Blood Brain Barrier+0.9525
Caco-2 permeable-0.6012
P-glycoprotein substrateNon-substrate0.7254
P-glycoprotein inhibitor INon-inhibitor0.7654
P-glycoprotein inhibitor IINon-inhibitor0.9757
Renal organic cation transporterNon-inhibitor0.9101
CYP450 2C9 substrateNon-substrate0.8409
CYP450 2D6 substrateNon-substrate0.8488
CYP450 3A4 substrateNon-substrate0.5649
CYP450 1A2 substrateNon-inhibitor0.8415
CYP450 2C9 substrateNon-inhibitor0.8494
CYP450 2D6 substrateNon-inhibitor0.9019
CYP450 2C19 substrateNon-inhibitor0.8269
CYP450 3A4 substrateNon-inhibitor0.9805
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.926
Ames testNon AMES toxic0.9133
CarcinogenicityCarcinogens 0.6724
BiodegradationReady biodegradable0.7562
Rat acute toxicity2.2812 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6277
hERG inhibition (predictor II)Non-inhibitor0.6966
Pharmacoeconomics
Manufacturers
  • Bioniche pharma usa llc
  • Elkins sinn div ah robins co inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous10 mg/mL
Injection, solutionintravenous30 mg/mL
Prices
Unit descriptionCostUnit
Sotradecol 3% vial33.0USD ml
Sotradecol 1% vial19.68USD ml
Tromboject 3 %3.77USD ml
Tromboject 1 %3.46USD ml
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 Solubility0.00262 mg/mLALOGPS
logP2.59ALOGPS
logP5.31ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity78.14 m3·mol-1ChemAxon
Polarizability35.74 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesC05BB04
AHFS Codes
  • 24:16.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

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