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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

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
[Enantiomeric separation of drugs with capillary electrophoresis with cyclodextrins].
2001
Allergic contact dermatitis from triethanolamine in a sunscreen.
2001 Jan
Effects of vaccination with several mycobacterial proteins and lipoproteins on Mycobacterium leprae infection of the mouse.
2001 Mar
Luminol chemiluminescence in unbuffered solutions with a cobalt(II)-ethanolamine complex immobilized on resin as catalyst and its application to analysis.
2001 Nov 1
Use of ferric chloride to identify salicylate-containing poisons.
2002
Effect of vehicles and penetration enhancers on the in vitro percutaneous absorption of tenoxicam through hairless mouse skin.
2002 Apr 2
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
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.
2003 Apr 22
Dynamic localization of SPE-9 in sperm: a protein required for sperm-oocyte interactions in Caenorhabditis elegans.
2003 Dec 3
A novel two-pore domain K+ channel, TRESK, is localized in the spinal cord.
2003 Jul 25
Synthesis of uniform anatase TiO2 nanoparticles by gel-sol method. 4. Shape 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
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
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
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
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
Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice.
2004 Jun
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
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
Ion chromatographic analysis of amines, alkanolamines, and associated anions in concrete.
2005 Mar
Photoreduction behavior of cytochrome c by zinc porphyrin in lipid media.
2005 May 13
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
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