U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H26O4S.C6H15NO3
Molecular Weight 415.5874
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIETHANOLAMINE LAURYL SULFATE

SMILES

CCCCCCCCCCCCOS(=O)(=O)O.C(CO)N(CCO)CCO

InChI

InChIKey=JZKFHQMONDVVNF-UHFFFAOYSA-N
InChI=1S/C12H26O4S.C6H15NO3/c1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15;8-4-1-7(2-5-9)3-6-10/h2-12H2,1H3,(H,13,14,15);8-10H,1-6H2

HIDE SMILES / InChI

Molecular Formula C6H15NO3
Molecular Weight 149.1884
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C12H26O4S
Molecular Weight 266.399
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created using several sources including: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/11340s16lbl.pdf; https://www.ons.org/intervention/trolamine-biafine®; https://www.ncbi.nlm.nih.gov/pubmed/?term=15084618; https://clinicaltrials.gov/ct2/show/NCT02729324; http://www.ncbi.nlm.nih.gov/pubmed/18441842

Trolamine, an organic compound, is the salt formed between triethanolamine and salicylic acid. It is widely used as a topical analgesic. 10% trolamine salicylate medical products sold over-the-counter such as are creams for temporarily relief of minor aches and pains of muscles and joints associated with arthritis, simple backache, lumbago, neuralgia, strains, bruises, and sprains. The FDA approved in 1958 otic solution drops containing triethanolamine polypeptide used in the ear to break down and loosen earwax was discontinued. Trolamine can enhance skin healing by recruiting macrophages and modifying the concentrations of various immunomodulators. Trolamine (Biafine; Genmedix Ltd, France) is commonly prescribed at the beginning of radiotherapy for preventing acute radiation-induced skin toxicity in China. Biafine has been studied in radiodermatitis and Phase 2 clinical trial has been initiated in 2016 by Sun Yat-sen University to establish the efficacy of trolamine (Biafine) for the management of radiation dermatitis in patients with nasopharyngeal carcinoma receiving IMRT.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
Volu-Firm

Approved Use

Unknown
Palliative
CERUMENEX

Approved Use

For removal of impacted cerumen prior to ear examination, otologic therapy and/or audiometry. CERUMENEX Eardrops should be used only with caution in external otitis.

Launch Date

-3.63571184E11
Doses

Doses

DosePopulationAdverse events​
5.38 mg 2 times / day multiple, topical
Studied dose
Dose: 5.38 mg, 2 times / day
Route: topical
Route: multiple
Dose: 5.38 mg, 2 times / day
Sources:
unhealthy, 21.6–84.9
n = 15
Health Status: unhealthy
Condition: Wound
Age Group: 21.6–84.9
Sex: M+F
Population Size: 15
Sources:
Disc. AE: Application site erythema...
AEs leading to
discontinuation/dose reduction:
Application site erythema (6.7%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Application site erythema 6.7%
Disc. AE
5.38 mg 2 times / day multiple, topical
Studied dose
Dose: 5.38 mg, 2 times / day
Route: topical
Route: multiple
Dose: 5.38 mg, 2 times / day
Sources:
unhealthy, 21.6–84.9
n = 15
Health Status: unhealthy
Condition: Wound
Age Group: 21.6–84.9
Sex: M+F
Population Size: 15
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Use of ferric chloride to identify salicylate-containing poisons.
2002
Molecular changes in the expression of human colonic nutrient transporters during the transition from normality to malignancy.
2002 Apr 22
Analysis of illicit amphetamine seizures by capillary zone electrophoresis.
2002 Dec 6
Synthesis and characterization of mesoporous indium tin oxide possessing an electronically conductive framework.
2002 Jul 24
Physicochemical determinants of linear alkylbenzene sulfonate (LAS) disposition in skin exposed to aqueous cutting fluid mixtures.
2002 Jun
Amines compounds as inhibitors of PCDD/Fs de novo formation on sintering process fly ash.
2002 Jun 15
Photobleaching of a solid photochromic medium by a Gaussian laser beam.
2002 May 20
The enhancing effect of a triethanolamine-ethanol-isopropyl myristate mixed system on the skin permeation of acidic drugs.
2002 Oct
Assessing changes in Cd phytoavailability to tomato in amended calcareous soils.
2002 Oct
Physiological function of the maltose operon regulator, MalR, in Lactococcus lactis.
2002 Sep 25
Sustaining pattern of phenformin hydrochloride using various polymers and waxes.
2002 Sep-Oct
Carcinostatic, protective, and adaptive activities of tris-(2-hydroxyethyl)ammonium salts of arylheteroacetic acids.
2002 Sep-Oct
Coordination and fluorescence of the intracellular Zn2+ probe [2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxy]acetic acid (Zinquin A) in ternary Zn2+ complexes.
2003 Apr 2
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.
2003 Apr 22
The use of complexation with alkanolamines to facilitate skin permeation of mefenamic acid.
2003 Aug 27
A comparative study between catalase gene therapy and the cardioprotector monohydroxyethylrutoside (MonoHER) in protecting against doxorubicin-induced cardiotoxicity in vitro.
2003 Dec 1
Dynamic localization of SPE-9 in sperm: a protein required for sperm-oocyte interactions in Caenorhabditis elegans.
2003 Dec 3
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
2003 Feb
Correlation between pK(a) and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope.
2003 Feb 7
Photovoltaic properties of self-assembled monolayers of porphyrins and porphyrin-fullerene dyads on ITO and gold surfaces.
2003 Jul 30
Capillary electrophoresis determinations of trace concentrations of inorganic ions in large excess of chloride: soft modelling using artificial neural networks for optimisation of electrolyte composition.
2003 Jun
Synthesis of uniform anatase TiO2 nanoparticles by gel-sol method. 4. Shape control.
2003 Mar 1
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.
2003 May-Jun
Extracting material parameters from x-ray attenuation: a CT feasibility study using kilovoltage synchrotron x-rays incident upon low atomic number absorbers.
2003 Oct 21
Molecular energy and electron transfer assemblies made of self-organized lipid-porphyrin bilayer vesicles.
2003 Oct 6
Carbopols as factors buffering triethanolamine interacting with artificial skin sebum.
2004
[The problem and improvement of colorimetric method for determination of sulfite in foods containing sulfur compounds].
2004 Dec
Mixture additives inhibit the dermal permeation of the fatty acid, ricinoleic acid.
2004 Feb 28
Evaluation of method of preparation of passive diffusion tubes for measurement of ambient nitrogen dioxide.
2004 Jan
Physicochemical and crystallographic characterization of mefenamic acid complexes with alkanolamines.
2004 Jan
Mechanical and water barrier properties of glutenin films influenced by storage time.
2004 Jan 14
Lactic acid production with lactate dehydrogenase using the visible light sensitization of zinc porphyrin.
2004 Jul
Triethanolamine zinc phosphite, (C6H13NO3)Zn2(HPO3): a templated network or a network of clusters?
2004 Jul 26
Integrative analysis of the mitochondrial proteome in yeast.
2004 Jun
Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice.
2004 Jun
Cubic phase prepared in an anionic/amphoteric surfactant/oleic acid/decane/water system and the relationship with the neighboring phase.
2004 Mar 30
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
NTP toxicology and carcinogenesis studies of triethanolamine (Cas No. 102-71-6) in B6C3F1 mice (dermal studies).
2004 May
A high-nuclearity "Celtic-ring" isopolyoxotungstate, [H12W36O120]12-, that captures trace potassium ions.
2004 Nov 3
Efficient photocurrent generation by self-assembled monolayers composed of 3 10-helical peptides carrying linearly spaced naphthyl groups at the side chains.
2004 Oct 13
Functionalized metal oxide clusters: synthesis, characterization, crystal structures, and magnetic properties of a novel series of fully reduced heteropolyoxovanadium cationic clusters decorated with organic ligands--[MVIV6O6[(OCH2CH2)2N(CH2CH2OH)]6]X (M = Li, X = Cl x LiCl; M = Na, X = Cl x H2O; M = Mg, X = 2Br x H2O; M = Mn, Fe, X = 2Cl; M = Co, Ni, X = 2Cl x H2O).
2004 Sep 20
Photosensitized hydrogen evolution from water using conjugated polymers wrapped in dendrimeric electrolytes.
2004 Sep 29
Frequent loss of RUNX3 gene expression in remnant stomach cancer and adjacent mucosa with special reference to topography.
2005 Feb 14
Polycationic dendrimers interact with RNA molecules: polyamine dendrimers inhibit the catalytic activity of Candida ribozymes.
2005 Jan 21
Generation of human antibody fragments against Streptococcus mutans using a phage display chain shuffling approach.
2005 Jan 25
New structural motifs in manganese single-molecule magnetism from the use of triethanolamine ligands.
2005 Jan 28
Ion chromatographic analysis of amines, alkanolamines, and associated anions in concrete.
2005 Mar
A factor analysis for complex systems containing nimesulide.
2005 Mar
Photoreduction behavior of cytochrome c by zinc porphyrin in lipid media.
2005 May 13
Effect of cationic micellar aggregates on the kinetics of oxidation of aminoalcohols by N-bromosuccinimide in alkaline medium.
2005 May 15
Patents

Sample Use Guides

Fill ear canal with ear drops of 10% triethanolamine Polypeptide Oleate-Condensate with the patient’s head tilted at a 45° angle. Insert cotton plug and allow to remain 15-30 minutes. Then gently flush with lukewarm water, using a soft rubber syringe (avoid excessive pressure). Exposure of skin outside the ear to the drug should be avoided. The procedure may be repeated if the first application fails to clear the impaction.
Route of Administration: Otic (auricular)
Penetration of triethanolamine into artificial skin sebum and its uplift were measured using 0.1 M aqueous triethanolamine solution.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:57:27 UTC 2021
Edited
by admin
on Sat Jun 26 09:57:27 UTC 2021
Record UNII
E8458C1KAA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIETHANOLAMINE LAURYL SULFATE
HSDB  
Systematic Name English
TEA-LAURYL SULFATE [VANDF]
Common Name English
TROLAMINE LAURYLSULFATE [WHO-DD]
Common Name English
TROLAMINE LAURYL SULFATE
II  
Common Name English
TRIETHANOLAMINE LAURYL SULPHATE
Systematic Name English
TEA LAURYL SULPHATE
Common Name English
DODECYL SULFATE TRIETHANOLAMINE
Systematic Name English
SULFURIC ACID, MONODODECYL ESTER, COMPD. WITH 2,2',2''-NITRILOTRIETHANOL (1:1)
Common Name English
TEA-LAURYL SULFATE [INCI]
Common Name English
TEA-LAURYL SULFATE
INCI   VANDF  
INCI  
Official Name English
TEA LAURYL SULFATE
Common Name English
TRIETHANOLAMINE LAURYL SULFATE [HSDB]
Common Name English
TROLAMINE LAURYL SULPHATE
Common Name English
TROLAMINE LAURYLSULFATE
WHO-DD  
Common Name English
TROLAMINE LAURYL SULFATE [II]
Common Name English
TEA-LAURYL SULPHATE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 79046
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
Code System Code Type Description
MESH
C044721
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
CONCEPT Industrial Aid
ECHA (EC/EINECS)
205-388-7
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
HSDB
2899
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
PUBCHEM
8777
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
NCI_THESAURUS
C84230
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
EPA CompTox
139-96-8
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
EVMPD
SUB04989MIG
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
FDA UNII
E8458C1KAA
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
RXCUI
1363986
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY RxNorm
CAS
139-96-8
Created by admin on Sat Jun 26 09:57:27 UTC 2021 , Edited by admin on Sat Jun 26 09:57:27 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY