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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 of TROLAMINE SALICYLATE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.48 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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
Palliative
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
Palliative
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
Palliative
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
Primary
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
Primary
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
Primary
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
238 min
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

Doses

DosePopulationAdverse 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:
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:
Other AEs: Redness, Scales...
Other AEs:
Redness
Scales
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
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:
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:
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
major
no
no
no
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
[Identification and quantification of exogenous metabolites in biological liquids with new development in NMR spectroscopy in one and two dimensions].
1999
[Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid].
1999 Feb
Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE).
1999 May
False-high blood salicylate levels in neonates with hyperbilirubinemia.
2000 Dec
The central catechol-O-methyltransferase inhibitor tolcapone increases striatal hydroxyl radical production in L-DOPA/carbidopa treated rats.
2001
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.
2001
The solvent shells of cluster ions produced by direct electric field extraction from glycerol/water mixtures.
2001
Comparison of the radical trapping ability of PBN, S-PPBN and NXY-059.
2001 Apr
A novel jasmonic acid-inducible rice myb gene associates with fungal infection and host cell death.
2001 Apr
Nucleotide sequence analysis of 5'-flanking region of salicylate hydroxylase gene, and identification and purification of a LysR-type regulator, SalR.
2001 Apr
Hereditary palmoplantar keratoderma (four cases in three generations).
2001 Feb
Induction of wound response gene expression in tomato leaves by ionophores.
2001 Feb
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
Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.
2001 Feb
Acetylsalicylic acid and other salicylates in relation to Stevens-Johnson syndrome and toxic epidermal necrolysis.
2001 Feb
Ethylene-dependent salicylic acid regulates an expanded cell death response to a plant pathogen.
2001 Feb
Molecular responses to aphid feeding in Arabidopsis in relation to plant defense pathways.
2001 Feb
The arabidopsis ISR1 locus controlling rhizobacteria-mediated induced systemic resistance is involved in ethylene signaling.
2001 Feb
The spinning disc reactor--studies on a novel TiO2 photocatalytic reactor.
2001 Feb
3-Hydroxybenzoic acid as an internal standard for the high-pressure liquid chromatography quantitation of salicylic acid in plants.
2001 Feb 1
Breakage and fusion of the TEL (ETV6) gene in immature B lymphocytes induced by apoptogenic signals.
2001 Feb 1
A hot pepper cDNA encoding a pathogenesis-related protein 4 is induced during the resistance response to tobacco mosaic virus.
2001 Feb 28
Characterization of PBZ1, a probenazole-inducible gene, in suspension-cultured rice cells.
2001 Jan
Increases in the mutation frequency at which fusidic acid-resistant Staphylococcus aureus arise with salicylate.
2001 Jan
Microfabrication of individual 200 microm diameter transdermal microconduits using high voltage pulsing in salicylic acid and benzoic acid.
2001 Jan
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.
2001 Jan
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
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
Cause of high variability in drug dissolution testing and its impact on setting tolerances.
2001 Jan
Reversed-phase high-performance liquid chromatography versus spectrophotometric assay for thimerosal in Cuban recombinant hepatitis B vaccine.
2001 Jan 12
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.
2001 Jan 15
Quantitative analysis of crystalline pharmaceuticals in powders and tablets by a pattern-fitting procedure using X-ray powder diffraction data.
2001 Jan 16
Increased sensitivity to sodium salicylate-induced apoptosis in drug-resistant leukemia L1210 cells.
2001 Jan-Feb
Combined cryotherapy/70% salicylic acid treatment for plantar verrucae.
2001 Jan-Feb
Interaction of the Arabidopsis receptor protein kinase Wak1 with a glycine-rich protein, AtGRP-3.
2001 Jul 13
Potentiometric determination of acetylsalicylic acid by sequential injection analysis (SIA) using a tubular salicylate-selective electrode.
2001 Mar
In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis.
2001 Mar 1
Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption.
2001 Mar 14
Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.
2001 Mar 5
Use of methyl salicylate as a simulant to predict the percutaneous absorption of sulfur mustard.
2001 Mar-Apr
Anti-inflammatory and antipyretic effects of Trigonella foenum-graecum leaves extract in the rat.
2001 May
Laryngeal oedema caused by accidental ingestion of Oil of Wintergreen.
2001 May 11
Patents

Sample Use Guides

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 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)
Record Version
  • Download
Name Type Language
TROLAMINE SALICYLATE
MART.   USP   VANDF   WHO-DD  
Common Name English
TEA-SALICYLATE
INCI  
INCI  
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
MI   VANDF  
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
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
NCI_THESAURUS C257
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
CFR 21 CFR 352.10
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C84231
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
EPA CompTox
2174-16-5
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
MESH
C032758
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
FDA UNII
H8O4040BHD
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
DRUG CENTRAL
4442
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
WIKIPEDIA
TROLAMINE SALICYLATE
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
MERCK INDEX
M11100
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY Merck Index
EVMPD
SUB04990MIG
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
PUBCHEM
25213
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
CAS
2174-16-5
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
DRUG BANK
DB11079
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107288
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
RXCUI
38866
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
218-531-3
Created by admin on Fri Jun 25 20:58:24 UTC 2021 , Edited by admin on Fri Jun 25 20:58:24 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY