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HomeProduct name listTYLOXAPOL

TYLOXAPOL

Synonym(s):4-(1,1,3,3-Tetramethylbutyl)phenol polymer with formaldehyde and oxirane

TYLOXAPOL Structural

What is TYLOXAPOL?

Toxicity

Acute oral LD50 in 1000 mg/kg in mouse and 5000 mg/kg in rat.

Description

Tyloxapol is a non-ionic liquid polymer of the alkylaryl polyether alcohol type. It has a wide range of uses as a surfactant (primarily for bronchopulmonary studies and drug delivery systems), an animal model inducer (used for induction of hyperlipidaemia in animals), and a reagent for biological studies (including studies of its mechanism of protection of macrophages against endotoxins and potential cytotoxicity).

Chemical properties

clear to hazy yellow to amber viscous liquid

Originator

Solacen

The Uses of TYLOXAPOL

Tyloxapol, is a nonionic liquid polymer of the alkyl aryl polyether alcohol type. It is used as a surfactant to aid liquefaction and removal of mucopurulent (containing mucus and pus) bronchopulmonary secretions. Tyloxapol also blocks plasma lipolytic activity.

The Uses of TYLOXAPOL

anthelmintic, hepatotoxic

What are the applications of Application

Tyloxapol is a nonionic liquid polymer of the alkyl aryl polyether alcohol type

Background

Tyloxapol is a non-ionic detergent often used as a surfactant.

Indications

Tyloxapol is an inhaled surfactant that assists in removing and liquefying and removing bronchopulmonary secretions with mucus and pus. Tyloxapol is administered either through nebulized solution or a stream of oxygen. Also investigated for use/treatment in cystic fibrosis and pediatric indications.

Definition

ChEBI: Tyloxapol is a polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions. It has a role as an inhibitor, an excipient, a surfactant and an apoptosis inducer.

Manufacturing Process

Srep 1: Into a 3-necked flask equipped with thermometer, mechanical agitator, and reflux condenser was charged the following: 412 g of α,α,γ,γ- tetramethylbutylphenol, 162 g of a 37% aqueous solution of formaldehyde, and 27.6 g of water. The mixture was agitated and heated to a temperature of 90°C. At this point, 246 g of oxalic acid and 0.92 g of Twitchell's reagent dissolved in 10 g of water were added. While being agitated, the reaction mixture was refluxed for 6 hours. 200 g of water and 384 g of toluene were added, and refluxing was continued for an hour.
Agitation was stopped and the contents of the flask were removed to a separatory funnel. The aqueous and resinous layers were separated and the solvent was removed from the resinous layer by vacuum distillation. After the removal of the solvent, heating at a reduced pressure of 1.5 to 2.5 mm and at a temperature of 245° to 250°C was continued for 4 1/2 hours. The condensate then had a viscosity of 4.0 poises when measured as a 60% solution in toluene and, on cooling, solidified to a brittle mass.
Step 2: A mixture of 118 parts of the product of Step 1, having hydroxyl number of 260, 2 parts of solid NaH, and 100 parts of toluene was heated to 125° to 150°C in an autoclave. Ethylene oxide was added slowly over a period of 2 1/2 hours until 261 parts of ethylene oxide were absorbed. This corresponds to 11 mols of ethylene oxide per mol of phenol in the product of Step 1. The toluene was then removed by steam distillation and the water by vacuum distillation at 10°C. The product was obtained as a viscous paste having a corrected hydroxyl number of 97. It was readily soluble in water and had marked detergent properties.

brand name

Superinone (Sterling Winthrop).

Therapeutic Function

Bronchodilator

General Description

Tyloxapol is a biocompatible surfactant

Mechanism of action

Tyloxapol, when injected IP, blocks plasma lipolytic activity, and thus the breakdown of triglyceride-rich lipoproteins. It has also been shown to be inhibitor of lipoprotein lipase, thus preventing triglyceride uptake.

Pharmacokinetics

It is used as a surfactant to aid liquefaction and removal of mucopurulent (containing mucus and pus) bronchopulmonary secretions. Tyloxapol also blocks plasma lipolytic activity, and thus the breakdown of triglyceride-rich lipoproteins.

Metabolism

Not Available

Properties of TYLOXAPOL

Density  1.1
Flash point: 113 °C
storage temp.  under inert gas (nitrogen or Argon) at 2–8 °C
solubility  Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form  Viscous Liquid
color  Clear to hazy yellow to amber
Merck  13,9901
InChI InChI=1S/C14H22O.C2H4O.CH2O/c1-13(2,3)10-14(4,5)11-6-8-12(15)9-7-11;1-2-3-1;1-2/h6-9,15H,10H2,1-5H3;1-2H2;1H2
CAS DataBase Reference 25301-02-4(CAS DataBase Reference)

Safety information for TYLOXAPOL

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for TYLOXAPOL

InChIKey MDYZKJNTKZIUSK-UHFFFAOYSA-N
SMILES C=O.C1OC1.C(C1C=CC(O)=CC=1)(C)(C)CC(C)(C)C

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