TROLAMINE

US Previously Marketed

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 Search

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
Sources: https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=TROLAMINE&audience=professional;
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

Condition	Modality	Targets	Highest Phase	Product
Sunburns 22 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a8276be2-93f1-4782-b206-93ea31036216	Inactive ingredient		Approved 8429	Volu-Firm Approved Use Unknown
Impacted cerumen 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/11340s16lbl.pdf	Palliative		Withdrawn	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf	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: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf	Disc. AE: Application site erythema... AEs leading to discontinuation/dose reduction: Application site erythema (6.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf	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: https://pubmed.ncbi.nlm.nih.gov/19681344 https://cdn.mdedge.com/files/s3fs-public/Document/September-2017/083060326.pdf

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B4-0536	http://www.3bsc.com/index/pro_info.php?id=18384
3B Scientific (Wuhan) Corp	3B4-0537	http://www.3bsc.com/index/pro_info.php?id=18385
3B Scientific (Wuhan) Corp	3B4-0538	http://www.3bsc.com/index/pro_info.php?id=18386
3B Scientific (Wuhan) Corp	3B4-2977	http://www.3bsc.com/index/pro_info.php?id=77610
AA Blocks	AA003UYI	http://www.aablocks.com/goods/Goods/detail?id=AA003UYI
Acadechem	ACDS-032071	http://www.acadechemical.com/product/106770
Achemica	ACMC-20ajek	http://www.achemica.com/prodinfo/?id=138096
Achemtek	0102-022738	http://www.achemtek.com/102-71-6
Acros Organics	AC139560025	https://www.fishersci.com/shop/products/triethanolamine-97-acros-organics/AC139560025
Acros Organics	AC421630025	https://www.fishersci.com/shop/products/triethanolamine-99-acros-organics-1/AC421630025
Acros Organics	AC421630250	https://www.fishersci.com/shop/products/triethanolamine-99-acros-organics/AC421630250
Alfa Aesar	L04486	https://www.alfa.com/en/catalog/L04486/
Alichem	490012088	http://www.alichem.com/en/products/102-71-6.html
Angene	AGN-PC-0DAJHK	http://www.angenechemical.com/productshow/AGN-PC-0DAJHK.html
Aurora Fine Chemicals LLC	A00.157.464	http://online.aurorafinechemicals.com/info?ID=A00.157.464
Aurora Fine Chemicals LLC	K02.098.739	http://online.aurorafinechemicals.com/info?ID=K02.098.739
Avantor Inc	101224-568	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101224-568
Avantor Inc	BT128875-100G	https://us.vwr.com/store/product/16637307/triethanolamine-trolamine-98
Avantor Inc	BT128875-2.5KG	https://us.vwr.com/store/product/16637307/triethanolamine-trolamine-98
Avantor Inc	BT128875-500G	https://us.vwr.com/store/product/16637307/triethanolamine-trolamine-98
Avantor Inc	JT9468-1	https://us.vwr.com/store/product/4563060/triethanolamine-trolamine-99-0-by-gc-baker-analyzed-j-t-baker
BOC Sciences	73205-32-0	https://www.bocsci.com/triethanolamine-d15-cas-73205-32-0-item-307498.html
BioSynth	J-525067	https://www.biosynth.com/en/products/all-products/products/J-525067.html
BroadPharm	BP-21029	https://www.broadpharm.com/web/product.php?catalog=BP-21029
Chem Scene	CS-5859	http://www.chemscene.com/102-71-6.html
Chemenu	CM116573	http://www.chemenu.com/products/CM116573
Chemspace	CSSS00000210588	https://chem-space.com/CSSS00000210588
Clearsynth	CS-EB-02183	https://www.clearsynth.com/en/CSEB02183.html
Clearsynth	CS-ER-02175	https://www.clearsynth.com/en/CSER02175.html
Fisher Chemical	T4071	https://www.fishersci.com/shop/products/triethanolamine-certified-fisher-chemical-3/p-203471
Fisher Chemical	T4074	https://www.fishersci.com/shop/products/triethanolamine-certified-fisher-chemical-3/p-203471
Fisher Chemical	T407500	https://www.fishersci.com/shop/products/triethanolamine-certified-fisher-chemical-3/p-203471
Fisher Chemical	T3504	https://www.fishersci.com/shop/products/triethanolamine-nf-fisher-chemical-2/p-203483
Fisher Chemical	T350500	https://www.fishersci.com/shop/products/triethanolamine-nf-fisher-chemical-2/p-203483
Glentham Life Sciences	GE0563	http://www.glentham.com/products/product/GE0563/
Hairui	HR123823	http://www.hairuichem.com/en/product/102-71-6.html
LGC Standards	DRE-C17831900	https://www.lgcstandards.com/US/en/p/DRE-C17831900
LGC Standards	MM1204.00	https://www.lgcstandards.com/US/en/p/MM1204.00
Matrix Scientific	99578	https://www.matrixscientific.com/099578.html
MedChem Express	HY-B1809	https://www.medchemexpress.com/Triethanolamine.html
MuseChem	I000173	https://www.musechem.com/product/I000173.html
Oakwood	242387	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=123386&ExtHyperLink=1
Otava	2828994	https://search.otavachemicals.com/#!/search?query=2828994&type=code&base=dbb
Parchem	25862	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-015862.aspx
Parchem	37993	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-85--027993.aspx
Parchem	37994	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-99--027994.aspx
Parchem	17809	http://www.parchem.com/chemical-supplier-distributor/Triethanolamine-99-Reagent-Grade-007809.aspx
Renno Tech	RP21273	http://www.rennotech.com/product_show.asp?id=26993
Sigma-Aldrich	30-4160_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/304160?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30-4170_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/304170?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	16303_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/16303?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	33729_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/33729?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1696958_USP	https://www.sigmaaldrich.com/catalog/product/usp/1696958?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S016414	http://www.sinfoobiotech.com/product/1019812
Smolecule	S772719	https://www.smolecule.com/products/s772719
Synthetic Heterocycles	ADAL1017515	http://www.synhet.com/products/ADAL1017515
THE BioTek	bt-253452	https://www.thebiotek.com/product/inhibitors/bt-253452
Vitas-M Laboratory	STL264185	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL264185&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL144787	https://www.vladachem.com/product.php?products=102-71-6
VladaChem	VL160744	https://www.vladachem.com/product.php?products=102-71-6
VladaChem	VL165654	https://www.vladachem.com/product.php?products=102-71-6
Yuhao Chemical	LQ0371	http://www.chemyuhao.com/102-71-6.html
abcr GmbH	AB174244	http://www.abcr.com/shop/en/AB174244
abcr GmbH	AB354583	http://www.abcr.com/shop/en/AB354583
abcr GmbH	AB354582	http://www.abcr.de/shop/en/AB354582
abcr GmbH	AB354584	http://www.abcr.de/shop/en/AB354584
abcr GmbH	AB354585	http://www.abcr.de/shop/en/AB354585
iChemical	EBD2205814	http://www.ichemical.com/products/102-71-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-1846755153	https://mcule.com/MCULE-1846755153/

PubMed

Title	Date	PubMed
Preliminary assessment of selected methacrylic acid--acrylic acid copolymers as factors buffering triethanolamine interacting with artificial skin sebum.	2001	11935937
[Enantiomeric separation of drugs with capillary electrophoresis with cyclodextrins].	2001	11928221
Fluorescent derivatization of nitrite ions with 2,3-diaminonaphthalene utilizing a pH gradient in a Y-shaped microchannel.	2001 Apr	11990573
In vitro percutaneous absorption of tenoxicam from pressure-sensitive adhesive matrices across the hairless mouse skin.	2001 Dec	11794539
Vanadium, molybdenum, and sodium triethanolamine complexes derived from an assembly system containing tetrathiometalate and triethanolamine.	2001 Jul 16	11442370
Luminol chemiluminescence in unbuffered solutions with a cobalt(II)-ethanolamine complex immobilized on resin as catalyst and its application to analysis.	2001 Nov 1	11721898
Effect of vehicles and penetration enhancers on the in vitro percutaneous absorption of tenoxicam through hairless mouse skin.	2002 Apr 2	11891070
Analysis of illicit amphetamine seizures by capillary zone electrophoresis.	2002 Dec 6	12498266
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	12906909
Dynamic localization of SPE-9 in sperm: a protein required for sperm-oocyte interactions in Caenorhabditis elegans.	2003 Dec 3	14653860
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	12558387
Capillary electrophoresis determinations of trace concentrations of inorganic ions in large excess of chloride: soft modelling using artificial neural networks for optimisation of electrolyte composition.	2003 Jun	12858398
Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum.	2003 Mar	12637103
Synthesis of uniform anatase TiO2 nanoparticles by gel-sol method. 4. Shape control.	2003 Mar 1	12651133
Substantial increase of the ordering temperature for [MnII/MoIII(CN)7]-based magnets as a function of the 3d ion site geometry: example of two supramolecular materials with Tc = 75 and 106 K.	2003 Mar 10	12611531
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.	2003 May-Jun	12793457
Reactivity with Tris(hydroxymethyl)aminomethane confounds immunodetection of acrolein-adducted proteins.	2003 Oct	14565760
Carbopols as factors buffering triethanolamine interacting with artificial skin sebum.	2004	15850295
Effect of some anionic polymers on pH of triethanolamine aqueous solutions.	2004	15497608
Evaluation of method of preparation of passive diffusion tubes for measurement of ambient nitrogen dioxide.	2004 Jan	14737464
Mechanical and water barrier properties of glutenin films influenced by storage time.	2004 Jan 14	14709016
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	15239850
Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice.	2004 Jun	15056812
Alternative approach to enhancing cation selectivity in ion chromatography.	2004 Jun 11	15250413
Titanatranes derailed: static and dynamic triethanolamine slippage induced by polyphenoxide chelation.	2004 Nov 1	15500337
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	15469265
Patch test results with the metalworking fluid series of the German Contact Dermatitis Research Group (DKG).	2004 Sep	15479200
Co phytoavailability for tomato in amended calcareous soils.	2005 Apr	15588767
Frequent loss of RUNX3 gene expression in remnant stomach cancer and adjacent mucosa with special reference to topography.	2005 Feb 14	15685235
Polycationic dendrimers interact with RNA molecules: polyamine dendrimers inhibit the catalytic activity of Candida ribozymes.	2005 Jan 21	15645021
Generation of human antibody fragments against Streptococcus mutans using a phage display chain shuffling approach.	2005 Jan 25	15667665
New structural motifs in manganese single-molecule magnetism from the use of triethanolamine ligands.	2005 Jan 28	15624221
Ion chromatographic analysis of amines, alkanolamines, and associated anions in concrete.	2005 Mar	15835735
A factor analysis for complex systems containing nimesulide.	2005 Mar	15666295
Photoreduction behavior of cytochrome c by zinc porphyrin in lipid media.	2005 May 13	15878113
Effect of cationic micellar aggregates on the kinetics of oxidation of aminoalcohols by N-bromosuccinimide in alkaline medium.	2005 May 15	15837498

Patents

Sample Use Guides

In Vivo Use Guide

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)

In Vitro Use Guide

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

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Name

Type

Language

TROLAMINE

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

Official Name

English

trolamine [INN]

Common Name

English

2,2',2''-NITRILOTRIETHANOL

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

D03AX12