General
Preferred name
Tetradecyl hydrogen sulfate (ester)
Synonyms
SODIUM TETRADECYL SULFATE ()
Tergitol 4 ()
Tetradecilsulfato de sodio ()
Sodium tetradecyl sulphate ()
Sotradecol ()
NSC-755887 ()
Tetradecyl sulfate de sodium ()
S.T.D. ()
Fibro-Vein ()
Fibrovein ()
Tetradecyl sulfate ()
TETRADECYL SULFURIC ACID ()
P&D ID
PD014792
CAS
139-88-8
300-52-7
Tags
available
drug
Approved by
FDA
First approval
1946
Drug Status
investigational
approved
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
TOXICITY
The intravenous LD50 of sodium tetradecyl sulfate in mice is 90 ± 5 mg/kg [L2030].; ; In the rat, the acute intravenous LD50 of sodium tetradecyl sulfate is estimated at 72 mg/kg and 108 mg/kg [L2030].; ; ; 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 [L2046].; ; **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 [L2037].; ; **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 [L2030].; ; **Allergic reactions** ; ; Hives, asthma, hay fever and anaphylactic shock have been reported with use of this drug [L2030]. ; ; **Mild systemic reactions **; ; Headache, nausea and vomiting [L2030].; ; **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 [L2030].; ; One death has been reported in a patient who received Sotradecol while receiving an anti-ovulatory agent [L2030]; ; 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 [L2030];
MOA
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 [L2037]. ; ; 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 [L2037].; ; The mechanical compression effect of submucosal edema, created by the injection of sclerosing agents, may also be responsible for acute hemostasis [L2037].
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 [L2030].; ; Sodium tetradecyl sulfate has been designated as an orphan drug by the FDA for the treatment of gastrointestinal bleeding due to esophageal varices [L2041].; ; ;
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 [L2040].; ; 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 [L2030].;
ROE
After an intravenously administered radiolabelled dose, 70% of the drug was recovered in the urine of rats within 24 hours post-dosing [L2042].; ; 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 [L2042].
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
11
ChEMBL Approved Drugs
ChEMBL Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMatrix
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
NPC Screening Collection
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
38
Molecular Weight
294.19
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
11
Ring Count
0
Aromatic Ring Count
0
cLogP
4.22
TPSA
63.6
Fraction CSP3
1.0
Chiral centers
2.0
Largest ring
0.0
QED
0.58
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Apoptosis
Source data
