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Details

Stereochemistry ACHIRAL
Molecular Formula C6H15NO3
Molecular Weight 149.1884
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROLAMINE

SMILES

C(CO)N(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

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

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
Physicochemical determinants of linear alkylbenzene sulfonate (LAS) disposition in skin exposed to aqueous cutting fluid mixtures.
2002 Jun
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
Photovoltaic properties of self-assembled monolayers of porphyrins and porphyrin-fullerene dyads on ITO and gold surfaces.
2003 Jul 30
The effect of pH and triethanolamine on sulfisoxazole complexation with hydroxypropyl-beta-cyclodextrin.
2003 Nov
Reactivity with Tris(hydroxymethyl)aminomethane confounds immunodetection of acrolein-adducted proteins.
2003 Oct
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
Effect of some anionic polymers on pH of triethanolamine aqueous solutions.
2004
Determination of alkanolamines in cattails (Typha latifolia) utilizing electrospray ionization with selected reaction monitoring and ion-exchange chromatography.
2004
Phase III randomized trial of Calendula officinalis compared with trolamine for the prevention of acute dermatitis during irradiation for breast cancer.
2004 Apr 15
Synthesis, structure and magnetism of new single molecule magnets composed of MnII2MnIII2 alkoxo-carboxylate bridged clusters capped by triethanolamine ligands.
2004 Apr 7
[The problem and improvement of colorimetric method for determination of sulfite in foods containing sulfur compounds].
2004 Dec
Complete charge pooling is prevented in viologen-based dendrimers by self-protection.
2004 Dec 3
Analysis of Tamm-Horsfall protein by high-performance liquid chromatography with native fluorescence.
2004 Feb 20
Mixture additives inhibit the dermal permeation of the fatty acid, ricinoleic acid.
2004 Feb 28
On-line collection/concentration and detection of sulfur dioxide in air by flow-injection spectrophotometry coupled with a chromatomembrane cell.
2004 Jan
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
Rheological characterization of topical carbomer gels neutralized to different pH.
2004 Jul
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
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
Alternative approach to enhancing cation selectivity in ion chromatography.
2004 Jun 11
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
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.
2004 May 4
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
Patch test results with the metalworking fluid series of the German Contact Dermatitis Research Group (DKG).
2004 Sep
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
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
Photopolymerization of poly(ethylene glycol) diacrylate on eosin-functionalized surfaces.
2004 Sep 28
Photosensitized hydrogen evolution from water using conjugated polymers wrapped in dendrimeric electrolytes.
2004 Sep 29
Co phytoavailability for tomato in amended calcareous soils.
2005 Apr
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 Fri Jun 25 21:12:56 UTC 2021
Edited
by admin
on Fri Jun 25 21:12:56 UTC 2021
Record UNII
9O3K93S3TK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
TRIETHANOLAMINE [INCI]
Common Name English
ETHANOL, 2,2',2''-NITRILOTRIS-
Systematic Name English
NSC-36718
Code English
TRIETHANOLAMINE [IARC]
Common Name English
TROLAMINE [VANDF]
Common Name English
TROLAMINE [WHO-DD]
Common Name English
TROLAMINE [EP]
Common Name English
TRIETHANOLAMINE [MI]
Common Name English
TRIETHANOLAMINE
INCI   MI   VANDF  
INCI  
Official 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 Fri Jun 25 21:12:56 UTC 2021 , Edited by admin on Fri Jun 25 21:12:56 UTC 2021
EPA PESTICIDE CODE 4208
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2768
Created by admin on Fri Jun 25 21:12:56 UTC 2021 , Edited by admin on Fri Jun 25 21:12:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL446061
Created by admin on Fri Jun 25 21:12:56 UTC 2021 , Edited by admin on Fri Jun 25 21:12:56 UTC 2021
PRIMARY
MERCK INDEX
M11100
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
TRIETHANOLAMINE
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
203-049-8
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
INN
561
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
CONCEPT Industrial Aid
USP_CATALOG
1696958
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY USP-RS
EVMPD
SUB12376MIG
Created by admin on Fri Jun 25 21:12:56 UTC 2021 , Edited by admin on Fri Jun 25 21:12:56 UTC 2021
PRIMARY
FDA UNII
9O3K93S3TK
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
EPA CompTox
102-71-6
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
RXCUI
38623
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB13747
Created by admin on Fri Jun 25 21:12:56 UTC 2021 , Edited by admin on Fri Jun 25 21:12:56 UTC 2021
PRIMARY
MESH
C009546
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
PUBCHEM
7618
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
NCI_THESAURUS
C80948
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
CAS
102-71-6
Created by admin on Fri Jun 25 21:12:56 UTC 2021 , Edited by admin on Fri Jun 25 21:12:56 UTC 2021
PRIMARY
HSDB
893
Created by admin on Fri Jun 25 21:12:57 UTC 2021 , Edited by admin on Fri Jun 25 21:12:57 UTC 2021
PRIMARY
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