TROLAMINE SALICYLATE

US Approved OTC

First marketed in 1860

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H6O3.C6H15NO3
Molecular Weight	287.3095
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc(c(c1)C(=O)O)O.C(CO)N(CCO)CCO

InChI

InChIKey=UEVAMYPIMMOEFW-UHFFFAOYSA-N

InChI=1S/C7H6O3.C6H15NO3/c8-6-4-2-1-3-5(6)7(9)10;8-4-1-7(2-5-9)3-6-10/h1-4,8H,(H,9,10);8-10H,1-6H2

HIDE SMILES / InChI

Molecular Formula	C6H15NO3
Molecular Weight	149.1884
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C7H6O3
Molecular Weight	138.121
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdfhttp://www.drugbank.ca/drugs/DB00936
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/salicylic-acid.html

Salicylic acid is obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics. Salicylic acid treats acne by causing skin cells to slough off more readily, preventing pores from clogging up. This effect on skin cells also makes salicylic acid an active ingredient in several shampoos meant to treat dandruff. Use of straight salicylic solution may cause hyperpigmentation on unpretreated skin for those with darker skin types (Fitzpatrick phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock. Subsalicylate in combination with bismuth form the popular stomach relief aid known commonly as Pepto-Bismol. When combined the two key ingredients help control diarrhea, nausea, heartburn, and even gas. It is also very mildly anti-biotic. Salicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-1 124 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 7728
Cyclooxygenase-2 189 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 7728
High mobility group protein B1 13 Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955	Inhibitor 7728	1.48 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Strains and sprains 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8043	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 1.20346562E12
Simple backache 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8043	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 1.20346562E12
Arthritis 86 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8043	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 1.20346562E12
Bruises 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8043	SALONPAS Approved Use Temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises Launch Date 1.20346562E12
Psoriasis 79 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8043	Salicylic Acid Approved Use Salicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date 1.35501119E12
Keratosis palmaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8043	Salicylic Acid Approved Use Salicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date 1.35501119E12
Ichthyosis vulgaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8043	Salicylic Acid Approved Use Salicylic Acid 6% is a topical aid in the removal of excessive keratin in hyperkeratotic skin disorders including verrucae, and the various ichthyoses (vulgaris, sex-linked and lamellar), keratosis palmaris and plantaris keratosis pilaris, pityriasis rubra pilaris, and psoriasis (including body, scalp, palms and soles). Launch Date 1.35501119E12

T_1/2

Value	Dose	Co-administered	Analyte	Population
238 min EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022354915364558	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		SALICYLIC ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	unhealthy, 23.05 ± 5.7 years n = 43 Health Status: unhealthy Condition: Acne vulgaris Age Group: 23.05 ± 5.7 years Sex: M+F Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	Other AEs: Redness, Scales... Other AEs: Redness Scales Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/

AEs

AE	Significance	Dose	Population
Redness		30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	unhealthy, 23.05 ± 5.7 years n = 43 Health Status: unhealthy Condition: Acne vulgaris Age Group: 23.05 ± 5.7 years Sex: M+F Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/
Scales		30 % 1 times / 2 weeks multiple, topical Dose: 30 %, 1 times / 2 weeks Route: topical Route: multiple Dose: 30 %, 1 times / 2 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/	unhealthy, 23.05 ± 5.7 years n = 43 Health Status: unhealthy Condition: Acne vulgaris Age Group: 23.05 ± 5.7 years Sex: M+F Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1601	substrate 936	substrate 1118

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 634 CYP2C19 910 CYP2E1 606 CYP2A6 485 CYP2B6 616 UGT1A1 393 UGT1A3 397 UGT1A4 330 UGT1A6 289 UGT1A7 221 UGT1A8 266 UGT1A9 357 UGT1A10 273 UGT2B4 233 UGT2B7 362 UGT2B15 191 UGT2B17 203	CYP2E1 117

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 871	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/	yes

Drug as victim

Target	Modality	Activity
CYP2A6 485	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2B6 616	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2E1 606	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	major
UGT1A4 330	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B15 191	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B17 203	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
CYP2C19 910	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C8 634	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C9 936	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2D6 1118	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP3A4 1601	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
UGT1A1 393	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A10 273	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A3 397	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A6 289	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A7 221	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A8 266	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A9 357	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B4 233	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B7 362	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16914	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16914
ChemicalBook	CB1680010	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1680010
MolPort	MolPort-001-769-476	https://www.molport.com/shop/molecule-link/MolPort-001-769-476
ZINC	ZINC000000001554	http://zinc15.docking.org/substances/ZINC000000001554
eMolecules	478035	https://www.emolecules.com/cgi-bin/more?vid=478035

PubMed

Title	Date	PubMed
In vitro release studies of methyl salicylate from the ointment bases and the commercial dermatological products.	1990	2371308
The central catechol-O-methyltransferase inhibitor tolcapone increases striatal hydroxyl radical production in L-DOPA/carbidopa treated rats.	2001	11314772
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.	2001	11296921
The solvent shells of cluster ions produced by direct electric field extraction from glycerol/water mixtures.	2001	11268133
Comparison of the radical trapping ability of PBN, S-PPBN and NXY-059.	2001 Apr	11328677
Cyanide-resistant alternative respiration is strictly correlated to intracellular peroxide levels in Acremonium chrysogenum.	2001 Apr	11328676
[Principal constituents from flowering aerial parts of wild pansy].	2001 Apr	11320336
A novel jasmonic acid-inducible rice myb gene associates with fungal infection and host cell death.	2001 Apr	11310740
Abnormal callose response phenotype and hypersusceptibility to Peronospoara parasitica in defence-compromised arabidopsis nim1-1 and salicylate hydroxylase-expressing plants.	2001 Apr	11310731
Evaluation of insulin permeability and effects of absorption enhancers on its permeability by an in vitro pulmonary epithelial system using Xenopus pulmonary membrane.	2001 Apr	11305600
Nucleotide sequence analysis of 5'-flanking region of salicylate hydroxylase gene, and identification and purification of a LysR-type regulator, SalR.	2001 Apr	11298739
Nitric oxide: comparative synthesis and signaling in animal and plant cells.	2001 Apr	11286923
Sodium salicylate increases CYP2E1 levels and enhances arachidonic acid toxicity in HepG2 cells and cultured rat hepatocytes.	2001 Apr	11259624
Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo).	2001 Apr 13	11334847
Nuclear factor-kappaB activation is not involved in a MPTP model of Parkinson's disease.	2001 Apr 17	11303744
Effect of fluvastatin, an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase, on nitric oxide-induced hydroxyl radical generation in the rat heart.	2001 Apr 30	11335104
[Tolerability of a selective cyclooxygenase-2-inhibitor (rofecoxib) in patients with intolerance reactions to nonsteroidal anti-inflammatory agents].	2001 Apr 6	11332239
Hereditary palmoplantar keratoderma (four cases in three generations).	2001 Feb	11328395
Induction of wound response gene expression in tomato leaves by ionophores.	2001 Feb	11289608
Isolation and preliminary characterization of the medium-chain fatty acid:CoA ligase responsible for activation of short- and medium-chain fatty acids in colonic mucosa from swine.	2001 Feb	11281196
Non-ionic micellar affinity capillary electrophoresis for analysis of interactions between micelles and drugs.	2001 Feb	11272320
Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.	2001 Feb	11266322
Acetylsalicylic acid and other salicylates in relation to Stevens-Johnson syndrome and toxic epidermal necrolysis.	2001 Feb	11259991
A hot pepper cDNA encoding a pathogenesis-related protein 4 is induced during the resistance response to tobacco mosaic virus.	2001 Feb 28	11266114
Molecular cloning of the nahG gene encoding salicylate hydroxylase from Pseudomonas fluorescens.	2001 Feb 28	11266111
Characterization of PBZ1, a probenazole-inducible gene, in suspension-cultured rice cells.	2001 Jan	11272832
Pathogen-induced expression of plant ATP: citrate lyase.	2001 Jan 19	11271173
Increased sensitivity to sodium salicylate-induced apoptosis in drug-resistant leukemia L1210 cells.	2001 Jan-Feb	11299731
Interaction of the Arabidopsis receptor protein kinase Wak1 with a glycine-rich protein, AtGRP-3.	2001 Jul 13	11335717
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.	2001 Jul 6	11306574
Selective suppression of CCAAT/enhancer-binding protein beta binding and cyclooxygenase-2 promoter activity by sodium salicylate in quiescent human fibroblasts.	2001 Jun 1	11278846
A recessive mutation in the Arabidopsis SSI2 gene confers SA- and NPR1-independent expression of PR genes and resistance against bacterial and oomycete pathogens.	2001 Mar	11309146
Signaling mediated by the closely related mammalian Rho family GTPases TC10 and Cdc42 suggests distinct functional pathways.	2001 Mar	11306516
The Arabidopsis downy mildew resistance gene, RPP13-Nd, functions independently of NDR1 and EDS1 and does not require the accumulation of salicylic acid.	2001 Mar	11277440
Development of QSARs to investigate the bacterial toxicity and biotransformation potential of aromatic heterocylic compounds.	2001 Mar	11272910
Interference by bilirubin in salicylate measurement.	2001 Mar	11269759
Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs.	2001 Mar	11256485
Flow-through UV spectrophotometric sensor for determination of (acetyl)salicylic acid in pharmaceutical preparations.	2001 Mar 23	11274811
ATR-FTIR spectroscopic investigations on the effect of solvents on the permeation of benzoic acid and salicylic acid through silicone membranes.	2001 Mar 23	11274806
Microdialysis of salicylic acid from viscous emulsion samples prior to high-performance liquid chromatographic determination.	2001 Mar 30	11307985
Use of methyl salicylate as a simulant to predict the percutaneous absorption of sulfur mustard.	2001 Mar-Apr	11288131
Differential vulnerability of basal and apical hair cells is based on intrinsic susceptibility to free radicals.	2001 May	11335071
Asbestos causes apoptosis in alveolar epithelial cells: role of iron-induced free radicals.	2001 May	11329530
Acanthoamoeba attachment to contact lenses.	2001 May	11320007
Anti-inflammatory and antipyretic effects of Trigonella foenum-graecum leaves extract in the rat.	2001 May	11297864
Binding of cosalane--a novel highly lipophilic anti-HIV agent--to albumin and glycoprotein.	2001 May	11288110
Measurement of free radical production by in vivo microdialysis during ischemia/reperfusion injury to skeletal muscle.	2001 May 1	11316577
Laryngeal oedema caused by accidental ingestion of Oil of Wintergreen.	2001 May 11	11335011
6-hydroxydopamine increases hydroxyl free radical production and DNA damage in rat striatum.	2001 May 8	11338183
In vitro dermal absorption of methyl salicylate, ethyl parathion, and malathion: first responder safety.	2007 Jun	17497409

Patents

Sample Use Guides

In Vivo Use Guide

adults 18 years and older: apply one patch to affected area and leave in place for up to 8-12 hours; if pain lasts lasts after using the first patch, a second patch may be applied for up to another 8 to 12 hours; use only one patch at a time; do not use more than 2 patches per day; do not use for more 3 days in a row

Route of Administration: Topical

In Vitro Use Guide

In vitro tests with fresh dermatomed (0.3 to 0.4 mm thick) female breast skin and one leg skin specimen were conducted in Bronaugh flow-through Teflon diffusion cells with three chemicals used to simulate chemical warfare agents: 14C-radiolabeled methyl salicylate (MES), ethyl parathion (PT), and malathion (MT), at three dose levels (2, 20, and 200 mM). Tests were conducted at a skin temperature of 29 degrees C using a brief 30-min exposure to the chemical and a 6.5-h receivor collection period. Rapid absorption of all three chemicals was observed, with MES absorbed about 10-fold faster than PT and MT. For MES, PT, and MT, respectively, there was 32%, 7%, and 12% absorption into the receivor solution at the low dose (2 mM), 17%, 2%, and 3% at the medium dose (20 mM), and 11%, 1%, and 1% at the high dose (200 mM) levels. Including the skin depot for MES, PT, and MT, respectively, there was 40%, 41%, and 21% (low dose), 26%, 16%, and 8% (medium dose), and 13%, 19%, and 10% (high does) absorption.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 20:58:24 UTC 2021` Edited by `admin` on `Fri Jun 25 20:58:24 UTC 2021`
Record UNII	H8O4040BHD
Record Status	`Validated (UNII)`
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Name

Type

Language

TROLAMINE SALICYLATE

Common Name

English

TEA-SALICYLATE

Official Name

English

TROLAMINE SALICYLATE [WHO-DD]

Common Name

English

TROLAMINE SALICYLATE [USP]

Common Name

English

TROLAMINE SALICYLATE [MART.]

Common Name

English

TRIETHANOLAMINE SALICYLATE [MI]

Common Name

English

NEOTAN W

Brand Name

English

TEA-SALICYLATE [INCI]

Common Name

English

TRIETHANOLAMINE SALICYLATE [VANDF]

Common Name

English

TROLAMINE SALICYLATE [USP MONOGRAPH]

Common Name

English

TRIETHANOLAMINE SALICYLATE

Systematic Name

English

BENZOIC ACID, 2-HYDROXY-, COMPD. WITH 2,2',2''-NITRILOTRIS(ETHANOL) (1:1)

Common Name

English

TRIETHANOLAMINE, SALICYLATE

Systematic Name

English

NEO HELIOPAN TS

Brand Name

English

Classification Tree Code System Code

CFR

21 CFR 352.20