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Details

Stereochemistry ACHIRAL
Molecular Formula C6H15NO3.ClH
Molecular Weight 185.649
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROLAMINE HYDROCHLORIDE

SMILES

Cl.OCCN(CCO)CCO

InChI

InChIKey=HHLJUSLZGFYWKW-UHFFFAOYSA-N
InChI=1S/C6H15NO3.ClH/c8-4-1-7(2-5-9)3-6-10;/h8-10H,1-6H2;1H

HIDE SMILES / InChI

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

1958
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
Fluorescent derivatization of nitrite ions with 2,3-diaminonaphthalene utilizing a pH gradient in a Y-shaped microchannel.
2001 Apr
Enantioselective separation of epoxides by capillary electrophoresis employing sulfated beta-cyclodextrin as chiral selector.
2001 Apr
Bis(triethanolamine)cadmium(II) and -mercury(II) saccharinates: seven-coordinate complexes containing both tri- and tetradentate triethanolamine ligands.
2001 Dec
Effects of vaccination with several mycobacterial proteins and lipoproteins on Mycobacterium leprae infection of the mouse.
2001 Mar
Extraction and separation of cationic surfactants from river sediments: application to a spectrophotometric determination of cationic surfactant in an aquatic environment using membrane filters.
2001 Nov
Luminol chemiluminescence in unbuffered solutions with a cobalt(II)-ethanolamine complex immobilized on resin as catalyst and its application to analysis.
2001 Nov 1
Application of membrane filters for spectrophotometric determination of cationic surfactants in river water and sediment.
2001 Nov-Dec
Chiral analysis of methylphenidate and dextromoramide by capillary electrophoresis.
2001 Sep 15
Analysis of illicit amphetamine seizures by capillary zone electrophoresis.
2002 Dec 6
Quantitation of nicotine in tobacco products by capillary electrophoresis.
2002 Jan-Feb
Physicochemical determinants of linear alkylbenzene sulfonate (LAS) disposition in skin exposed to aqueous cutting fluid mixtures.
2002 Jun
Performances and application of a passive sampling method for the simultaneous determination of nitrogen dioxide and sulfur dioxide in ambient air.
2002 Nov
The enhancing effect of a triethanolamine-ethanol-isopropyl myristate mixed system on the skin permeation of acidic drugs.
2002 Oct
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.
2003 Apr 22
Enantiomeric separation of TAPP, H-Tyr-(D)Ala-Phe-Phe-NH(2), by capillary electrophoresis using 18-crown-6-tetracarboxylic acid as a chiral selector.
2003 Aug 15
The use of complexation with alkanolamines to facilitate skin permeation of mefenamic acid.
2003 Aug 27
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
Equilibria of mononuclear oxomolybdenum(VI) complexes of triethanolamine. A multinuclear dynamic magnetic resonance study of structure and exchange mechanisms.
2003 Jul
A novel two-pore domain K+ channel, TRESK, is localized in the spinal cord.
2003 Jul 25
Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum.
2003 Mar
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.
2003 May-Jun
Reactivity with Tris(hydroxymethyl)aminomethane confounds immunodetection of acrolein-adducted proteins.
2003 Oct
Identification of selenium species in urine by ion-pairing HPLC-ICP-MS using laboratory-synthesized standards.
2003 Oct
Direct and fast capillary zone electrophoretic method for the determination of Gleevec and its main metabolite in human urine.
2003 Sep 5
Effect of some anionic polymers on pH of triethanolamine aqueous solutions.
2004
Synthesis, structure and magnetism of new single molecule magnets composed of MnII2MnIII2 alkoxo-carboxylate bridged clusters capped by triethanolamine ligands.
2004 Apr 7
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
Quantitation of biomarkers of exposure to nitrogen mustards in urine from rats dosed with nitrogen mustards and from an unexposed human population.
2004 Jul-Aug
Integrative analysis of the mitochondrial proteome in yeast.
2004 Jun
Alternative approach to enhancing cation selectivity in ion chromatography.
2004 Jun 11
NTP toxicology and carcinogenesis studies of triethanolamine (Cas No. 102-71-6) in B6C3F1 mice (dermal studies).
2004 May
Titanatranes derailed: static and dynamic triethanolamine slippage induced by polyphenoxide chelation.
2004 Nov 1
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
Determination of volatile corrosion inhibitors by capillary electrophoresis.
2004 Oct 8
Determination of diethanolamine or N-methyldiethanolamine in high ammonium concentration matrices by capillary electrophoresis with indirect UV detection: application to the analysis of refinery process waters.
2004 Sep
Co phytoavailability for tomato in amended calcareous soils.
2005 Apr
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
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.
Name Type Language
TROLAMINE HYDROCHLORIDE
Common Name English
TRIS(2-HYDROXYETHYL)AMMONIUM CHLORIDE
Systematic Name English
TRIETHANOLAMINE HYDROCHLORIDE [MI]
Common Name English
2-(BIS(2-HYDROXYETHYL)AMINO)ETHANOL HYDROCHLORIDE
Systematic Name English
TEA-HYDROCHLORIDE [INCI]
Common Name English
ETHANOL, 2,2',2''-NITRILOTRIS-, HYDROCHLORIDE (1:1)
Systematic Name English
TRIETHANOLAMINE HYDROCHLORIDE
MI  
Systematic Name English
TRIETHANOL AMMONIUM CHLORIDE
Systematic Name English
TEA-HYDROCHLORIDE
INCI  
INCI  
Official Name English
Code System Code Type Description
MESH
C009546
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY
FDA UNII
R297UJ9QDY
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY
DAILYMED
R297UJ9QDY
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY
PUBCHEM
101814
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY
MERCK INDEX
m11100
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID1052321
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
211-284-2
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY
CAS
637-39-8
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY
RXCUI
1368178
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY RxNorm
CHEBI
132753
Created by admin on Fri Dec 15 15:13:38 GMT 2023 , Edited by admin on Fri Dec 15 15:13:38 GMT 2023
PRIMARY