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Details

Stereochemistry ACHIRAL
Molecular Formula C6H15NO3
Molecular Weight 149.1882
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Trolamine

SMILES

OCCN(CCO)CCO

InChI

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

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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Preliminary assessment of selected methacrylic acid--acrylic acid copolymers as factors buffering triethanolamine interacting with artificial skin sebum.
2001
[Enantiomeric separation of drugs with capillary electrophoresis with cyclodextrins].
2001
Enantioselective separation of epoxides by capillary electrophoresis employing sulfated beta-cyclodextrin as chiral selector.
2001 Apr
In situ hybridization: use of 35S-labeled probes on paraffin tissue sections.
2001 Apr
Comparative studies of various run buffers for chiral capillary electrophoresis using chiral crown ether as a chiral selector.
2001 Dec
In vitro percutaneous absorption of tenoxicam from pressure-sensitive adhesive matrices across the hairless mouse skin.
2001 Dec
Bis(triethanolamine)cadmium(II) and -mercury(II) saccharinates: seven-coordinate complexes containing both tri- and tetradentate triethanolamine ligands.
2001 Dec
Vanadium, molybdenum, and sodium triethanolamine complexes derived from an assembly system containing tetrathiometalate and triethanolamine.
2001 Jul 16
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
[Determination of sulfite residues in foods by using the modified rankine apparatus and HPLC].
2001 Oct
Effect of vehicles and penetration enhancers on the in vitro percutaneous absorption of tenoxicam through hairless mouse skin.
2002 Apr 2
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
Carcinostatic, protective, and adaptive activities of tris-(2-hydroxyethyl)ammonium salts of arylheteroacetic acids.
2002 Sep-Oct
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
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
2003 Feb
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
Photovoltaic properties of self-assembled monolayers of porphyrins and porphyrin-fullerene dyads on ITO and gold surfaces.
2003 Jul 30
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
Determination of alkanolamines in cattails (Typha latifolia) utilizing electrospray ionization with selected reaction monitoring and ion-exchange chromatography.
2004
[The problem and improvement of colorimetric method for determination of sulfite in foods containing sulfur compounds].
2004 Dec
Analysis of Tamm-Horsfall protein by high-performance liquid chromatography with native fluorescence.
2004 Feb 20
Physicochemical and crystallographic characterization of mefenamic acid complexes with alkanolamines.
2004 Jan
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
Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice.
2004 Jun
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.
2004 May 4
A high-nuclearity "Celtic-ring" isopolyoxotungstate, [H12W36O120]12-, that captures trace potassium ions.
2004 Nov 3
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
Frequent loss of RUNX3 gene expression in remnant stomach cancer and adjacent mucosa with special reference to topography.
2005 Feb 14
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
TRIETHANOLAMINE
INCI   MI   VANDF  
INCI  
Preferred Name English
Trolamine
EP   HSDB   II   INN   MART.   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
TROLAMINE [MART.]
Common Name English
TROLAMINE [EP MONOGRAPH]
Common Name English
TRIETHANOLAMINE [VANDF]
Common Name English
TROLAMINE [II]
Common Name English
TROLAMINE [HSDB]
Common Name English
ETHANOL, 2,2',2''-NITRILOTRIS-
Systematic Name English
TROLAMINE [EP IMPURITY]
Common Name English
NSC-36718
Code English
Trolamine [WHO-DD]
Common Name English
TRIETHANOLAMINE [IARC]
Common Name English
TROLAMINE [VANDF]
Common Name English
TRIETHANOLAMINE [MI]
Common Name English
trolamine [INN]
Common Name English
2,2',2''-NITRILOTRIETHANOL
Systematic Name English
Classification Tree Code System Code
WHO-ATC D03AX12
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
EPA PESTICIDE CODE 4208
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2768
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL446061
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
MERCK INDEX
m11100
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
TRIETHANOLAMINE
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-049-8
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
INN
561
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PRIMARY
CHEBI
28621
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PRIMARY
NCI_THESAURUS
C45678
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CONCEPT Industrial Aid
EVMPD
SUB12376MIG
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PRIMARY
FDA UNII
9O3K93S3TK
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PRIMARY
EPA CompTox
DTXSID9021392
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PRIMARY
RS_ITEM_NUM
1696958
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PRIMARY
RXCUI
38623
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PRIMARY RxNorm
DRUG BANK
DB13747
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PRIMARY
SMS_ID
100000079034
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PRIMARY
NSC
36718
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
DAILYMED
9O3K93S3TK
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
MESH
C009546
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
PUBCHEM
7618
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
NCI_THESAURUS
C80948
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
CAS
102-71-6
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY
HSDB
893
Created by admin on Mon Mar 31 18:17:35 GMT 2025 , Edited by admin on Mon Mar 31 18:17:35 GMT 2025
PRIMARY