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targets (2)
for drugs
Identification
Name Sodium Tetradecyl Sulfate
Accession Number DB00464 (APRD00575)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Monotetradecylsulfate sodium salt
  • S.T.D.
  • Sodium myristyl sulfate
  • STD
  • Tetradecyl hydrogen sulphate
  • Tetradecyl sodium sulfate
  • Tetradecyl sulfate
  • Tetradecyl sulfuric Acid
Brand names
  • Niaproof-4
  • Sotradecol
  • Tergitol-4
  • Texapon K 14
Brand name mixtures Not Available
Categories
  • Surface-Active Agents
  • Sclerosing Agents
CAS number 1191-50-0
Weight Average: 294.451
Monoisotopic: 294.186480138
Chemical Formula C14H30O4S
InChI Key InChIKey=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)
Plain Text
IUPAC Name
(tetradecyloxy)sulfonic acid
SMILES
CCCCCCCCCCCCCCOS(O)(=O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Sulfuric Acids and Derivatives
  • Sulfate Esters
Substructures
  • Hydroxy Compounds
  • Sulfuric Acids and Derivatives
  • Sulfonyls
  • Sulfate Esters
Pharmacology
Indication For the treatment of small uncomplicated varicose veins of the lower extremities that show simple dilation with competent valves.
Pharmacodynamics Sodium 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 action Sodium 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity LD50=1250 mg/kg (Orally in rat); LD50=3 ml/kg (Skin in rat)
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bioniche pharma usa llc
  • Elkins sinn div ah robins co inc
Packagers
Dosage forms
Form Route Strength
Solution Intravenous
Prices
Unit description Cost Unit
Sotradecol 3% vial 33.0 USD ml
Sotradecol 1% vial 19.68 USD ml
Tromboject 3 % 3.77 USD ml
Tromboject 1 % 3.46 USD ml
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 2.62e-03 g/l ALOGPS
logP 2.59 ALOGPS
logP 5.31 ChemAxon Molconvert
logS -5.05 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 63.60 ChemAxon Molconvert
rotatable bond count 14 ChemAxon Molconvert
refractivity 78.14 ChemAxon Molconvert
polarizability 35.74 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 5248 Link_out
PubChem Substance 46505919 Link_out
ChemSpider 5058 Link_out
Therapeutic Targets Database DAP001276 Link_out
PharmGKB PA451439 Link_out
Drug Product Database 363332 Link_out
RxList http://www.rxlist.com/cgi/generic2/sotradecol.htm Link_out
Drugs.com http://www.drugs.com/cdi/sodium-tetradecyl-sulfate.html Link_out
ATC Codes
  • C05BB04
AHFS Codes
  • 24:16.00
PDB Entries Not Available
FDA label Not Available
MSDS show (52.2 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Vitamin K-dependent protein C

Pharmacological action: yes
Actions: inhibitor

Protein C is a vitamin K-dependent serine protease that regulates blood coagulation by inactivating factors Va and VIIIa in the presence of calcium ions and phospholipids

Organism class: human
UniProt ID: P04070 Link_out
Gene: PROC Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inhibitor

Anticoagulant plasma protein; it is a cofactor to activated protein C in the degradation of coagulation factors Va and VIIIa. It helps to prevent coagulation and stimulating fibrinolysis

Organism class: human
UniProt ID: P07225 Link_out
Gene: PROS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 November 12, 2010 09:00

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.