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

Molecular Formula C6H15NO3
Molecular Weight 149.1882
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

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
[Enantiomeric separation of drugs with capillary electrophoresis with cyclodextrins].
2001
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
Application of membrane filters for spectrophotometric determination of cationic surfactants in river water and sediment.
2001 Nov-Dec
Molecular changes in the expression of human colonic nutrient transporters during the transition from normality to malignancy.
2002 Apr 22
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
Amines compounds as inhibitors of PCDD/Fs de novo formation on sintering process fly ash.
2002 Jun 15
Photobleaching of a solid photochromic medium by a Gaussian laser beam.
2002 May 20
Performances and application of a passive sampling method for the simultaneous determination of nitrogen dioxide and sulfur dioxide in ambient air.
2002 Nov
Sustaining pattern of phenformin hydrochloride using various polymers and waxes.
2002 Sep-Oct
Coordination and fluorescence of the intracellular Zn2+ probe [2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxy]acetic acid (Zinquin A) in ternary Zn2+ complexes.
2003 Apr 2
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
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
2003 Feb
Expression and function of bradykinin receptors in microglia.
2003 Feb 21
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
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
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
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
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
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
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
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
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
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
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 Dec 15 16:03:16 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:16 GMT 2023
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
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 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
EPA PESTICIDE CODE 4208
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
Code System Code Type Description
DRUG CENTRAL
2768
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL446061
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
MERCK INDEX
m11100
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
TRIETHANOLAMINE
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-049-8
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
INN
561
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
CHEBI
28621
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
CONCEPT Industrial Aid
EVMPD
SUB12376MIG
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
FDA UNII
9O3K93S3TK
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID9021392
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
RS_ITEM_NUM
1696958
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
RXCUI
38623
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB13747
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
SMS_ID
100000079034
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
NSC
36718
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
DAILYMED
9O3K93S3TK
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
MESH
C009546
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
PUBCHEM
7618
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
NCI_THESAURUS
C80948
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
CAS
102-71-6
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
HSDB
893
Created by admin on Fri Dec 15 16:03:16 GMT 2023 , Edited by admin on Fri Dec 15 16:03:16 GMT 2023
PRIMARY
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