Sodium tetradecyl sulfate

Identification

Summary

Sodium tetradecyl sulfate is an anionic surfactant used to treat varicose veins of the lower extremities.

Brand Names
Tromboject
Generic Name
Sodium tetradecyl sulfate
DrugBank Accession Number
DB00464
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 316.43
Monoisotopic: 316.16842487
Chemical Formula
C14H29NaO4S
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 sulfate
  • Sodium tetradecyl sulphate
  • Sodium tetradecylsulfate
  • STS
  • Tetradecilsulfato sodico
  • Tetradecyl sodium sulfate
  • Tetradecyl sulfate de sodium

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Humans
AVitamin K-dependent protein S
inhibitor
Humans
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

Adverse Effects
Medicalerrors
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Toxicity

LD50=1250 mg/kg (Orally in rat); LD50=3 ml/kg (Skin in rat)

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

Products
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International/Other Brands
Fibro-Vein
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SotradecolSolution1 %IntravenousMylan PharmaceuticalsNot applicableNot applicableCanada flag
SotradecolSolution3 %IntravenousMylan PharmaceuticalsNot applicableNot applicableCanada flag
Tromboject 1% Inj 10mg/mlSolution10 mg / mLIntravenousOmega Laboratories Ltd1987-12-31Not applicableCanada flag
Tromboject 3% Inj 30mg/mlSolution30 mg / mLIntravenousOmega Laboratories Ltd1987-12-31Not applicableCanada flag
Trombovar Inj 1%Solution1 %IntravenousTherapex Division De E Z Em Canada Inc1976-12-312007-09-04Canada flag
Trombovar Inj 3%Solution3 %IntravenousTherapex Division De E Z Em Canada Inc1976-12-312007-09-04Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Sodium Tetradecyl SulfateInjection, solution30 mg/1mLIntravenousLeucadia Pharmaceuticals2019-12-09Not applicableUS flag

Categories

ATC Codes
C05BB04 — Sodium tetradecyl sulfate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Alkyl sulfate / Hydrocarbon derivative / Organic alkali metal salt / Organic oxide / Organic oxygen compound / Organic salt / Organic sodium salt / Organooxygen compound / Sulfate-ester
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic sodium salt (CHEBI:75273)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Q1SUG5KBD6
CAS number
139-88-8
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

References

General References
Not Available
KEGG Drug
D06882
PubChem Compound
23665772
PubChem Substance
46505919
ChemSpider
8440
RxNav
9913
ChEBI
75273
ChEMBL
CHEMBL1200354
Therapeutic Targets Database
DAP001276
PharmGKB
PA164746759
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sodium_tetradecyl_sulfate
AHFS Codes
  • 24:16.00 — Sclerosing Agents
MSDS
Download (52.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentVaricosities of the great saphenous vein1
4WithdrawnTreatmentSuperficial Venous Insufficiency, Varicose Veins1
2RecruitingTreatmentVenous Insufficiency1
1, 2CompletedTreatmentEpistaxis / Hereditary Haemorrhagic Telangiectasia (HHT)1
0RecruitingTreatmentCosmesis / Cost Effectiveness / Leg edema / Pain1
Not AvailableTerminatedHealth Services ResearchVaricosities of the great saphenous vein1
Not AvailableTerminatedTreatmentVenous Disease1

Pharmacoeconomics

Manufacturers
  • Bioniche pharma usa llc
  • Elkins sinn div ah robins co inc
Packagers
  • Angiodynamics
  • Bioniche Pharma
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous
Injection, solutionIntravenous30 mg/1mL
SolutionIntravenous10 mg / mL
SolutionIntravenous30 mg / mL
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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 14, 2021 11:41