Sodium Tetradecyl Sulfate

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
Synonyms
  • 7-Ethyl-2-methyl-4-undecanol sulfate sodium salt
  • 7-ethyl-2-methyl-4-undecanolsulfate, sodium salt
  • Natrii tetradecylis sulfa
  • Sodium 2-methyl-7-ethylundecanol-4-sulfate
  • Sodium 7-ethyl-2-methyl-4-undecanol sulfate
  • Sodium tetradecyl sulphate
  • Sodium tetradecylsulfate
  • STS
  • Tetradecilsulfato sodico
  • Tetradecyl sodium sulfate
  • Tetradecyl sulfate de sodium
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SotradecolSolution3 %IntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
SotradecolSolution1 %IntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Tromboject 1% Inj 10mg/mlSolution10 mgIntravenousOmega Laboratories Ltd1987-12-31Not applicableCanada
Tromboject 3% Inj 30mg/mlSolution30 mgIntravenousOmega Laboratories Ltd1987-12-31Not applicableCanada
Trombovar Inj 1%Solution1 %IntravenousTherapex Division De E Z Em Canada Inc1976-12-312007-09-04Canada
Trombovar Inj 3%Solution3 %IntravenousTherapex Division De E Z Em Canada Inc1976-12-312007-09-04Canada
International/Other Brands
Fibro-Vein
Categories
UNII
Q1SUG5KBD6
CAS number
139-88-8
Weight
Average: 316.43
Monoisotopic: 316.16842487
Chemical Formula
C14H29NaO4S
InChI Key
FVEFRICMTUKAML-UHFFFAOYSA-M
InChI
InChI=1S/C14H30O4S.Na/c1-5-7-8-13(6-2)9-10-14(11-12(3)4)18-19(15,16)17;/h12-14H,5-11H2,1-4H3,(H,15,16,17);/q;+1/p-1
IUPAC Name
sodium 7-ethyl-2-methylundecan-4-yl sulfate
SMILES
[Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O

Pharmacology

Indication

For the treatment of small uncomplicated varicose veins of the lower extremities that show simple dilation with competent valves.

Structured Indications
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.

TargetActionsOrganism
AVitamin K-dependent protein C
inhibitor
Human
AVitamin K-dependent protein S
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D06882
PubChem Compound
23665772
PubChem Substance
46505919
ChemSpider
8440
ChEBI
75273
ChEMBL
CHEMBL1200354
Therapeutic Targets Database
DAP001276
PharmGKB
PA164746759
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
ATC Codes
C05BB04 — Sodium tetradecyl sulfate
AHFS Codes
  • 24:16.00 — Sclerosing Agents
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2WithdrawnTreatmentBrain and Central Nervous System Tumors / Cancer, Breast / Cognitive/Functional Effects / Drug/Agent Toxicity by Tissue/Organ / Psychosocial Effects of Cancer and Its Treatment1
2CompletedTreatmentNicotine Dependence1
2RecruitingTreatmentIncompetent accessory saphenous veins1
2TerminatedTreatmentBrain and Central Nervous System Tumors / Drug/Agent Toxicity by Tissue/Organ / Malignant Lymphomas / Thrombocytopenias1
4RecruitingTreatmentVaricosities of the great saphenous vein1
4WithdrawnTreatmentSuperficial Venous Insufficiency, Varicose Veins1
Not AvailableCompletedTreatmentHereditary Haemorrhagic Telangiectasia (HHT) / Nasal Bleeding1
Not AvailableTerminatedPreventionCancers1
Not AvailableTerminatedTreatmentVenous Disease1

Pharmacoeconomics

Manufacturers
  • Bioniche pharma usa llc
  • Elkins sinn div ah robins co inc
Packagers
Dosage forms
FormRouteStrength
SolutionIntravenous10 mg
SolutionIntravenous30 mg
SolutionIntravenous1 %
SolutionIntravenous3 %
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00798 mg/mLALOGPS
logP3.97ALOGPS
logP5.04ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity76.65 m3·mol-1ChemAxon
Polarizability33.26 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8494
CYP450 2D6 inhibitorNon-inhibitor0.9019
CYP450 2C19 inhibitorNon-inhibitor0.8269
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This 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).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic sulfuric acids and derivatives
Sub Class
Sulfuric acid esters
Direct Parent
Sulfuric acid monoesters
Alternative Parents
Alkyl sulfates / Organooxygen compounds / Organic sodium salts / Organic oxides / Hydrocarbon derivatives
Substituents
Alkyl sulfate / Sulfate-ester / Sulfuric acid monoester / Organic alkali metal salt / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organic sodium salt / Organic salt / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic sodium salt (CHEBI:75273)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type endopeptidase activity
Specific Function
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 (PubMed:25618265). Exerts ...
Gene Name
PROC
Uniprot ID
P04070
Uniprot Name
Vitamin K-dependent protein C
Molecular Weight
52070.82 Da
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:17016423]
  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:1344580]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  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. doi: 10.1016/j.ejvs.2009.03.026. Epub 2009 May 12. [PubMed:19442540]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Endopeptidase inhibitor activity
Specific Function
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.
Gene Name
PROS1
Uniprot ID
P07225
Uniprot Name
Vitamin K-dependent protein S
Molecular Weight
75121.905 Da
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. doi: 10.1016/j.ejvs.2009.03.026. Epub 2009 May 12. [PubMed:19442540]
  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:1344580]

Drug created on June 13, 2005 07:24 / Updated on January 15, 2018 08:43