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
Enantioselective separation of epoxides by capillary electrophoresis employing sulfated beta-cyclodextrin as chiral selector.	2001 Apr	11340974
Comparative studies of various run buffers for chiral capillary electrophoresis using chiral crown ether as a chiral selector.	2001 Dec	11824603
Bis(triethanolamine)cadmium(II) and -mercury(II) saccharinates: seven-coordinate complexes containing both tri- and tetradentate triethanolamine ligands.	2001 Dec	11740089
Extraction and separation of cationic surfactants from river sediments: application to a spectrophotometric determination of cationic surfactant in an aquatic environment using membrane filters.	2001 Nov	11759511
[Determination of sulfite residues in foods by using the modified rankine apparatus and HPLC].	2001 Oct	11775359
Effect of vehicles and penetration enhancers on the in vitro percutaneous absorption of tenoxicam through hairless mouse skin.	2002 Apr 2	11891070
Quantitation of nicotine in tobacco products by capillary electrophoresis.	2002 Jan-Feb	11878587
Amines compounds as inhibitors of PCDD/Fs de novo formation on sintering process fly ash.	2002 Jun 15	12099476
Sustaining pattern of phenformin hydrochloride using various polymers and waxes.	2002 Sep-Oct	12481378
Aspartic proteinase napsin is a useful marker for diagnosis of primary lung adenocarcinoma.	2003 Apr 22	12698189
The use of complexation with alkanolamines to facilitate skin permeation of mefenamic acid.	2003 Aug 27	12927383
A comparative study between catalase gene therapy and the cardioprotector monohydroxyethylrutoside (MonoHER) in protecting against doxorubicin-induced cardiotoxicity in vitro.	2003 Dec 1	14647150
Dynamic localization of SPE-9 in sperm: a protein required for sperm-oocyte interactions in Caenorhabditis elegans.	2003 Dec 3	14653860
Expression and function of bradykinin receptors in microglia.	2003 Feb 21	12551746
A novel two-pore domain K+ channel, TRESK, is localized in the spinal cord.	2003 Jul 25	12754259
Preliminary assessment of alginic acid as a factor buffering triethanolamine interacting with artificial skin sebum.	2003 Mar	12637103
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
Modification and validation of the pyromellitic acid electrolyte for the capillary electrophoretic determination of anions.	2003 May 2	12800938
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.	2003 May-Jun	12793457
The effect of pH and triethanolamine on sulfisoxazole complexation with hydroxypropyl-beta-cyclodextrin.	2003 Nov	14592694
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	14620065
Determination of alkanolamines in cattails (Typha latifolia) utilizing electrospray ionization with selected reaction monitoring and ion-exchange chromatography.	2004	15282789
Phase III randomized trial of Calendula officinalis compared with trolamine for the prevention of acute dermatitis during irradiation for breast cancer.	2004 Apr 15	15084618
[The problem and improvement of colorimetric method for determination of sulfite in foods containing sulfur compounds].	2004 Dec	15794092
Mixture additives inhibit the dermal permeation of the fatty acid, ricinoleic acid.	2004 Feb 28	14700524
Physicochemical and crystallographic characterization of mefenamic acid complexes with alkanolamines.	2004 Jan	14648644
Rheological characterization of topical carbomer gels neutralized to different pH.	2004 Jul	15290859
Lactic acid production with lactate dehydrogenase using the visible light sensitization of zinc porphyrin.	2004 Jul	15239004
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].	2004 May	15218738
Titanatranes derailed: static and dynamic triethanolamine slippage induced by polyphenoxide chelation.	2004 Nov 1	15500337
A high-nuclearity "Celtic-ring" isopolyoxotungstate, [H12W36O120]12-, that captures trace potassium ions.	2004 Nov 3	15506722
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	15338092

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