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

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

-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
Fluorescent derivatization of nitrite ions with 2,3-diaminonaphthalene utilizing a pH gradient in a Y-shaped microchannel.
2001 Apr
In vitro percutaneous absorption of tenoxicam from pressure-sensitive adhesive matrices across the hairless mouse skin.
2001 Dec
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
Chiral analysis of methylphenidate and dextromoramide by capillary electrophoresis.
2001 Sep 15
Physicochemical determinants of linear alkylbenzene sulfonate (LAS) disposition in skin exposed to aqueous cutting fluid mixtures.
2002 Jun
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
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.
2003 Apr 22
A comparative study between catalase gene therapy and the cardioprotector monohydroxyethylrutoside (MonoHER) in protecting against doxorubicin-induced cardiotoxicity in vitro.
2003 Dec 1
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
Synthesis of uniform anatase TiO2 nanoparticles by gel-sol method. 3. Formation process and size control.
2003 Mar 1
Modification and validation of the pyromellitic acid electrolyte for the capillary electrophoretic determination of anions.
2003 May 2
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.
2003 May-Jun
The effect of pH and triethanolamine on sulfisoxazole complexation with hydroxypropyl-beta-cyclodextrin.
2003 Nov
Identification of selenium species in urine by ion-pairing HPLC-ICP-MS using laboratory-synthesized standards.
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
Direct and fast capillary zone electrophoretic method for the determination of Gleevec and its main metabolite in human urine.
2003 Sep 5
Carbopols as factors buffering triethanolamine interacting with artificial skin sebum.
2004
Determination of alkanolamines in cattails (Typha latifolia) utilizing electrospray ionization with selected reaction monitoring and ion-exchange chromatography.
2004
Analysis of Tamm-Horsfall protein by high-performance liquid chromatography with native fluorescence.
2004 Feb 20
On-line collection/concentration and detection of sulfur dioxide in air by flow-injection spectrophotometry coupled with a chromatomembrane cell.
2004 Jan
Lactic acid production with lactate dehydrogenase using the visible light sensitization of zinc porphyrin.
2004 Jul
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
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.
2004 May 4
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
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
Generation of human antibody fragments against Streptococcus mutans using a phage display chain shuffling approach.
2005 Jan 25
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.
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
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
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 Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
EPA PESTICIDE CODE 4208
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
Code System Code Type Description
DRUG CENTRAL
2768
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
ChEMBL
CHEMBL446061
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
MERCK INDEX
M11100
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY Merck Index
WIKIPEDIA
TRIETHANOLAMINE
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
ECHA (EC/EINECS)
203-049-8
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
INN
561
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
CHEBI
28621
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
CONCEPT Industrial Aid
EVMPD
SUB12376MIG
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
FDA UNII
9O3K93S3TK
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
EPA CompTox
DTXSID9021392
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
RS_ITEM_NUM
1696958
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
RXCUI
38623
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY RxNorm
DRUG BANK
DB13747
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
NSC
36718
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
DAILYMED
9O3K93S3TK
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
MESH
C009546
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
PUBCHEM
7618
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
NCI_THESAURUS
C80948
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
CAS
102-71-6
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY
HSDB
893
Created by admin on Fri Dec 16 19:05:29 UTC 2022 , Edited by admin on Fri Dec 16 19:05:29 UTC 2022
PRIMARY