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 57 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 3315
Cyclooxygenase-2 86 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 3315
High mobility group protein B1 8 Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955	Inhibitor 3315	1.48 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Strains and sprains 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 4033	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 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 4033	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 50 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 4033	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 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 4033	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 32 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 4033	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 8 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 4033	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 8 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 4033	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 882	substrate 530	substrate 610

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 354 CYP2C19 500 CYP2E1 332 CYP2A6 266 CYP2B6 338 UGT1A1 198 UGT1A3 195 UGT1A4 171 UGT1A6 148 UGT1A7 114 UGT1A8 137 UGT1A9 180 UGT1A10 136 UGT2B4 120 UGT2B7 182 UGT2B15 96 UGT2B17 97	CYP2E1 63

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 467	inducer 772 Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/	yes

Drug as victim

Target	Modality	Activity
CYP2A6 266	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2B6 338	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2E1 332	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	major
UGT1A4 171	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B15 96	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B17 97	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
CYP2C19 500	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C8 354	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C9 530	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2D6 610	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP3A4 882	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
UGT1A1 198	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A10 136	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A3 195	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A6 148	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A7 114	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A8 137	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A9 180	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B4 120	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B7 182	substrate 1689 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
[Identification and quantification of exogenous metabolites in biological liquids with new development in NMR spectroscopy in one and two dimensions].	1999	10216993
[Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid].	1999 Feb	10221197
Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE).	1999 May	10366903
False-high blood salicylate levels in neonates with hyperbilirubinemia.	2000 Dec	11128247
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
A novel jasmonic acid-inducible rice myb gene associates with fungal infection and host cell death.	2001 Apr	11310740
Nucleotide sequence analysis of 5'-flanking region of salicylate hydroxylase gene, and identification and purification of a LysR-type regulator, SalR.	2001 Apr	11298739
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
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
Ethylene-dependent salicylic acid regulates an expanded cell death response to a plant pathogen.	2001 Feb	11208023
Molecular responses to aphid feeding in Arabidopsis in relation to plant defense pathways.	2001 Feb	11161062
The arabidopsis ISR1 locus controlling rhizobacteria-mediated induced systemic resistance is involved in ethylene signaling.	2001 Feb	11161023
The spinning disc reactor--studies on a novel TiO2 photocatalytic reactor.	2001 Feb	11100791
3-Hydroxybenzoic acid as an internal standard for the high-pressure liquid chromatography quantitation of salicylic acid in plants.	2001 Feb 1	11161302
Breakage and fusion of the TEL (ETV6) gene in immature B lymphocytes induced by apoptogenic signals.	2001 Feb 1	11157492
A hot pepper cDNA encoding a pathogenesis-related protein 4 is induced during the resistance response to tobacco mosaic virus.	2001 Feb 28	11266114
Characterization of PBZ1, a probenazole-inducible gene, in suspension-cultured rice cells.	2001 Jan	11272832
Increases in the mutation frequency at which fusidic acid-resistant Staphylococcus aureus arise with salicylate.	2001 Jan	11192496
Microfabrication of individual 200 microm diameter transdermal microconduits using high voltage pulsing in salicylic acid and benzoic acid.	2001 Jan	11168796
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.	2001 Jan	11161607
Ion channel-forming alamethicin is a potent elicitor of volatile biosynthesis and tendril coiling. Cross talk between jasmonate and salicylate signaling in lima bean.	2001 Jan	11154344
Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors.	2001 Jan	11154339
Cause of high variability in drug dissolution testing and its impact on setting tolerances.	2001 Jan	11113646
Reversed-phase high-performance liquid chromatography versus spectrophotometric assay for thimerosal in Cuban recombinant hepatitis B vaccine.	2001 Jan 12	11217023
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.	2001 Jan 15	11163537
Quantitative analysis of crystalline pharmaceuticals in powders and tablets by a pattern-fitting procedure using X-ray powder diffraction data.	2001 Jan 16	11165078
Increased sensitivity to sodium salicylate-induced apoptosis in drug-resistant leukemia L1210 cells.	2001 Jan-Feb	11299731
Combined cryotherapy/70% salicylic acid treatment for plantar verrucae.	2001 Jan-Feb	11202766
Interaction of the Arabidopsis receptor protein kinase Wak1 with a glycine-rich protein, AtGRP-3.	2001 Jul 13	11335717
Potentiometric determination of acetylsalicylic acid by sequential injection analysis (SIA) using a tubular salicylate-selective electrode.	2001 Mar	11248498
In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis.	2001 Mar 1	11182525
Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption.	2001 Mar 14	11250091
Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.	2001 Mar 5	11254191
Use of methyl salicylate as a simulant to predict the percutaneous absorption of sulfur mustard.	2001 Mar-Apr	11288131
Anti-inflammatory and antipyretic effects of Trigonella foenum-graecum leaves extract in the rat.	2001 May	11297864
Laryngeal oedema caused by accidental ingestion of Oil of Wintergreen.	2001 May 11	11335011

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