Identification
- Summary
Tetradecyl hydrogen sulfate (ester) is an anionic surfactant used to treat small uncomplicated varicose veins.
- Brand Names
- Sotradecol
- Generic Name
- Tetradecyl hydrogen sulfate (ester)
- DrugBank Accession Number
- DB11328
- Background
Sodium tetradecyl sulfate is an anionic surface-active agent which is used for its wetting properties in the industry and is also used in medicine as a blood vessel irritant and sclerosing agent for hemorrhoids and varicose veins 2.
Sodium tetradecyl sulfate has been widely used since the 1950s, and in 1978 the first successful report of injecting a 1% solution into spider angiomas in 144 patients was made. Also noted was an unspecified number of episodes of epidermal necrosis without significant long-term effects and a 30% incidence of post-sclerosis pigmentation that resolved within a few months 3.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Tetradecyl hydrogen sulfate (ester) (DB11328)
- Weight
- Average: 294.45
Monoisotopic: 294.18648062 - Chemical Formula
- C14H30O4S
- Synonyms
- 7-Ethyl-2-methyl-4-undecanol sulfate
- Tetradecyl hydrogen sulfate
Pharmacology
- Indication
Sotradecol (sodium tetradecyl sulfate injection) is indicated in the treatment of small, uncomplicated varicose veins of the legs showing simple dilation, with competent valves 1.
Sodium tetradecyl sulfate has been designated as an orphan drug by the FDA for the treatment of gastrointestinal bleeding due to esophageal varices 8.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Gastrointestinal bleeding •••••••••••• Treatment of Uncomplicated competent valves, simple dilation varicose veins of legs •••••••••••• - Contraindications & Blackbox Warnings
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Telangiectasias or varicose veins occur in about 33% of adult women and about 15% of adult men. Sclerotherapy with sotradecol is widely used in the treatment of varicose veins 7.
Sotradecol (sodium tetradecyl sulfate injection) is a sclerosing agent. Intravenous (IV) injection of this agent causes blood vessel intima inflammation and thrombus formation. This normally occludes the injected vein, leading to a series of events. Subsequent formation of fibrous tissue results in partial or complete vein obliteration that may be temporary or permanent 1.
- Mechanism of action
When injected directly into a vein, sodium tetradecyl sulfate causes intimal inflammation and venous thrombus formation, which then results in occlusion of the vein. Following this sequence of events, fibrous tissue forms and causes partial to complete obliteration of the vein, which may be temporary or permanent. An important role of this drug, as well as other sclerosing agents, is to control active hemorrhage and encourage hemostasis. This may be due to the esophageal and vascular smooth muscle spasm induced by the sclerosing agent 5.
During acute and active bleeding, the sodium tetradecyl sulfate injected directly into the esophageal varices may dissipate rapidly, as the varices have a much higher blood volume/flow rate and no functioning valves 5.
The mechanical compression effect of submucosal edema, created by the injection of sclerosing agents, may also be responsible for acute hemostasis 5.
Target Actions Organism AEndothelial protein C receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
In humans, a large proportion (75%) of an injected dose of radiolabelled 3% sodium tetradecyl sulfate rapidly disappeared from the empty varicose vein injection site into communicating blood vessels with rapid entry into the deep veins of the calf 9.
In rats, at 72 hours after intravenous dosing of radiolabelled sodium tetradecyl sulfate, tissue levels of radiolabelled matter found in sample tissues (liver, kidney, lipid and skeletal muscle) were measured as very low. Although there was some evidence of radiolabel associated with the injection site, the levels were negligible 9.
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
After an intravenously administered radiolabelled dose, 70% of the drug was recovered in the urine of rats within 24 hours post-dosing 9.
At the end of the 72 hour post-dose period, 73.5% of the radiolabel had been recovered from the urine and 18.2% recovered from the faeces 9.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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The intravenous LD50 of sodium tetradecyl sulfate in mice is 90 ± 5 mg/kg 1.
In the rat, the acute intravenous LD50 of sodium tetradecyl sulfate is estimated at 72 mg/kg and 108 mg/kg 1.
Adverse events are below:
Deep venous thrombosis
Because of the risk of deep vein thrombosis, patients must be evaluated for valvular competency and deep venous patency before treatment is initiated and slow injections of a small volume (< 2 mL) should be injected. It is recommended that patients be monitored post-treatment for both deep vein thrombosis and pulmonary embolism 12.
Air embolism
Stroke, transient ischemic attack, myocardial infarction, and impaired cardiac function have been associated with tetradecyl sulfate administration. Such sequelae may be caused by air embolism 5.
Local reaction
Local reactions including pain, itching or ulceration at the site of injection with permanent discoloration may remain along the path of the treated/sclerosed vein segment. Sloughing and/or necrosis of surrounding tissue may occur following extravasation from the injection site 1.
Allergic reactions
Hives, asthma, hay fever and anaphylactic shock have been reported with use of this drug 1.
*Mild systemic reactions *
Headache, nausea and vomiting 1.
Death A minimum of 6 deaths have reported with the use of Sotradecol. Four incidences of anaphylactic shock resulting in death have been reported in patients who received this drug 1.
One death has been reported in a patient who received Sotradecol while receiving an anti-ovulatory agent 1
Another death (from lethal pulmonary embolism) has been reported in a 36-year-old female treated with sodium tetradecyl acetate and was not taking oral contraceptive therapy 1
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Fibro-vein (Australasian Medical and Scientific Limited) / Fibro-Vein 3% (STD) / Fibrovein (Craveri) / Veinfibro (STD Pharmaceutical Products)
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image (sotradecol) Sodium Tetradecyl Sulfate Injection, solution 30 mg/1mL Intravenous HF Acquisition Co LLC, DBA HealthFirst 2021-06-25 Not applicable US 
Sodium Tetradecyl Sulfate Injection, solution 10 mg/1mL Intravenous HF Acquisition Co LLC, DBA HealthFirst 2021-07-18 Not applicable US Sotradecol Injection, solution 10 mg/1mL Intravenous Mylan Institutional LLC 2013-04-29 Not applicable US Sotradecol Injection, solution 30 mg/1mL Intravenous A-S Medication Solutions 2013-04-29 Not applicable US Sotradecol Injection, solution 30 mg/1mL Intravenous Angiodynamics 2004-12-01 2015-09-30 US
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 6326W0DRHY
- CAS number
- 300-52-7
- InChI Key
- GROJOWHVXQYQGN-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H30O4S/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)
- IUPAC Name
- [(7-ethyl-2-methylundecan-4-yl)oxy]sulfonic acid
- SMILES
- CCCCC(CC)CCC(CC(C)C)OS(O)(=O)=O
References
- General References
- SOTRADECOL- tetradecyl hydrogen sulfate (ester) injection, solution [Link]
- Sotradecol, PubChem [Link]
- Sodium tetradecyl sulfate [Link]
- Sodium Tetradecyl Sulfate [Link]
- PDR Sotradecol [Link]
- Evaluation of sodium tetradecyl sulfate and polidocanol as sclerosants for leg telangiectasia based on histological evaluation with clinical correlation [Link]
- Anaphylactoid Reaction After the Use of Sodium Tetradecyl Sulfate: A Case Report [Link]
- Drug Approval Package [Link]
- NZ Drug Safe Fibrovein [Link]
- Intralesional 3% Sodium Tetradecyl Sulfate for Treatment of Cutaneous Kaposi's Sarcoma [Link]
- Sodium tetradecyl sulfate actions [Link]
- Sotradecol [Link]
- External Links
- ChemSpider
- 8441
- 1370424
- ChEBI
- 75275
- ChEMBL
- CHEMBL1201345
- MSDS
- Download (253 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Venous Malformations 1 4 Completed Treatment Varicosities of the great saphenous vein 1 4 Withdrawn Treatment Superficial Venous Insufficiency, Varicose Veins 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 10 mg/1mL Injection, solution Intravenous 30 mg/1mL Injection, solution Parenteral 0.2 % Injection, solution Parenteral 0.5 % Injection, solution Parenteral 1 % Injection, solution Parenteral 3 % - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
Property Value Source melting point (°C) 199 MSDS - Predicted Properties
Property Value Source Water Solubility 0.0104 mg/mL ALOGPS logP 1.98 ALOGPS logP 5.04 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) -1.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 63.6 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 77.77 m3·mol-1 Chemaxon Polarizability 33.53 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-4930000000-40ee004ed0ce1c09d253 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-1090000000-2147066aeb5646debe1b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-8090000000-4ce90d21cf3823810d67 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001d-9710000000-3ff81197b983f0b17d3d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-9200000000-c0f097338ddb277602c3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-053s-9000000000-56b158c6df785e5701e4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor activity
- Specific Function
- Binds activated protein C. Enhances protein C activation by the thrombin-thrombomodulin complex; plays a role in the protein C pathway controlling blood coagulation.
- Gene Name
- PROCR
- Uniprot ID
- Q9UNN8
- Uniprot Name
- Endothelial protein C receptor
- Molecular Weight
- 26671.245 Da
References
- Sodium tetradecyl sulfate actions [Link]
Drug created at December 03, 2015 16:52 / Updated at February 13, 2021 10:52