Tetradecyl hydrogen sulfate (ester)

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

Similar Structures

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.

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Associated Conditions

Contraindications & Blackbox Warnings

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Pharmacodynamics

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	antagonist	Humans

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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Toxicity

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
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Abacavir	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.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level.
Aclidinium	Aclidinium may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level.
Acrivastine	Acrivastine may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level.
Acyclovir	Acyclovir may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level.
Adefovir dipivoxil	Adefovir dipivoxil may decrease the excretion rate of Tetradecyl hydrogen sulfate (ester) which could result in a higher serum level.

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Food Interactions

No interactions found.

Products

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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
(sotradecol) Sodium Tetradecyl Sulfate	Injection, solution	30 mg/1mL	Intravenous	HF Acquisition Co LLC, DBA HealthFirst	2021-06-25	Not applicable
Sodium Tetradecyl Sulfate	Injection, solution	10 mg/1mL	Intravenous	HF Acquisition Co LLC, DBA HealthFirst	2021-07-18	Not applicable
Sotradecol	Injection, solution	30 mg/1mL	Intravenous	Angiodynamics	2004-12-01	2015-09-30
Sotradecol	Injection, solution	30 mg/1mL	Intravenous	Mylan Institutional LLC	2013-04-29	Not applicable
Sotradecol	Injection, solution	10 mg/1mL	Intravenous	Angiodynamics	2004-12-01	2015-09-30
Sotradecol	Injection, solution	10 mg/1mL	Intravenous	A-S Medication Solutions	2013-04-29	Not applicable
Sotradecol	Injection, solution	10 mg/1mL	Intravenous	Mylan Institutional LLC	2013-04-29	Not applicable
Sotradecol	Injection, solution	30 mg/1mL	Intravenous	A-S Medication Solutions	2013-04-29	Not applicable

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
RxNav: 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

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: Not Available

Targets

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Details1. Endothelial protein C receptor

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

Tetradecyl hydrogen sulfate (ester)

Identification

Structure for Tetradecyl hydrogen sulfate (ester) (DB11328)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References