ETHYL SALICYLATE

US Approved OTC

First marketed in 1860

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10O3
Molecular Weight	166.1739
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C1=CC=CC=C1O

InChI

InChIKey=GYCKQBWUSACYIF-UHFFFAOYSA-N

InChI=1S/C9H10O3/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6,10H,2H2,1H3

HIDE SMILES / InChI

Molecular Formula	C9H10O3
Molecular Weight	166.1739
Charge	0
Count

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

Description
Sources: http://www.drugbank.ca/drugs/DB00936https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/salicylic-acid.html

Methyl salicylate (or methyl 2-hydroxybenzoate), also known as wintergreen oil, is a natural product and is present in white wine, tea, porcini mushroom Boletus edulis, Bourbon vanilla, clary sage, red sage and fruits including cherry, apple, raspberry, papaya and plum. Methyl salicylate is topically used in combination with methanol and under brand name SALONPAS to temporarily relieves mild to moderate aches and pains of muscles and joints associated with: strains, sprains, simple backache, arthritis, bruises. The precise mechanism of action of methyl salicylate is not known, but there is suggested, that it cause dilation of the capillaries thereby increasing blood flow to the area.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8297
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8297
High mobility group protein B1 13 Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955	Inhibitor 8297	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 8429	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 8429	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 89 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8429	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 8429	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 84 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8429	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 8429	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 8429	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 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 693 CYP2C19 991 CYP2E1 667 CYP2A6 543 CYP2B6 664 UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 291 UGT2B4 249 UGT2B7 389 UGT2B15 203 UGT2B17 213	CYP2E1 128

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 970	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/	yes

Drug as victim

Target	Modality	Activity
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	major
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B17 213	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A8 283	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B7 389	substrate 3367 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
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.	2001	11296921
Hydroxyl radical adduct of 5-aminosalicylic acid: a potential marker of ozone-induced oxidative stress.	2001	11235916
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
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
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
Ascorbic acid prevents 3,4-methylenedioxymethamphetamine (MDMA)-induced hydroxyl radical formation and the behavioral and neurochemical consequences of the depletion of brain 5-HT.	2001 Apr	11170222
Uptake mechanism of valproic acid in human placental choriocarcinoma cell line (BeWo).	2001 Apr 13	11334847
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
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
Increased leukotriene production by food additives in patients with atopic dermatitis and proven food intolerance.	2001 Feb	11251628
Ethylene-dependent salicylic acid regulates an expanded cell death response to a plant pathogen.	2001 Feb	11208023
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
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
Non-uniform mapping of stress-induced, motility-related charge movement in the outer hair cell plasma membrane.	2001 Jan	11212214
Increases in the mutation frequency at which fusidic acid-resistant Staphylococcus aureus arise with salicylate.	2001 Jan	11192496
Probenazole induces systemic acquired resistance in Arabidopsis with a novel type of action.	2001 Jan	11169191
Manipulation of salicylate content in Arabidopsis thaliana by the expression of an engineered bacterial salicylate synthase.	2001 Jan	11169183
Microfabrication of individual 200 microm diameter transdermal microconduits using high voltage pulsing in salicylic acid and benzoic acid.	2001 Jan	11168796
Effect of 4-trifluoromethyl derivatives of salicylate on nuclear factor kappaB-dependent transcription in human astrocytoma cells.	2001 Jan	11159705
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
Salicylate and cocaine: interactive toxicity during chicken mid-embryogenesis.	2001 Jan 15	11163537
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism.	2001 Jan 15	11145657
Quantitative analysis of crystalline pharmaceuticals in powders and tablets by a pattern-fitting procedure using X-ray powder diffraction data.	2001 Jan 16	11165078
Synthesis and metal binding properties of salicylate-, catecholate-, and hydroxypyridinonate-functionalized dendrimers.	2001 Jan 5	11205020
Release of salicylic acid, diclofenac acid and diclofenac acid salts from isotropic and anisotropic nonionic surfactant systems across rat skin.	2001 Jan 5	11165822
Broad-spectrum mildew resistance in Arabidopsis thaliana mediated by RPW8.	2001 Jan 5	11141561
Combined cryotherapy/70% salicylic acid treatment for plantar verrucae.	2001 Jan-Feb	11202766
Quantitative analysis of hydroxyl radicals in the anterior optic nerve of the cat following transient ischemia.	2001 Jan-Feb	11195744
Interaction of the Arabidopsis receptor protein kinase Wak1 with a glycine-rich protein, AtGRP-3.	2001 Jul 13	11335717
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
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
Quantitative analysis of analgoantipyretics in dosage form using planar chromatography.	2001 Mar	11248516
In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis.	2001 Mar 1	11182525
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
Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.	2001 Mar 5	11254191
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
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

Patents

Sample Use Guides

In Vivo Use Guide

The preferable method of use is to apply Salicylic Acid 6% thoroughly to the affected area and to cover the treated area at night after washing and before retiring. Preferably, the skin should be hydrated for a least five minutes prior to application.

Route of Administration: Topical

In Vitro Use Guide

Salicylic acid inhibited hippuric acid formation in the homogenates obtained from the specimens of human liver with IC50 value 0.19 mM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:08:47 UTC 2023` Edited by `admin` on `Fri Dec 15 15:08:47 UTC 2023`
Record UNII	555U6TZ2MV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYL SALICYLATE

Systematic Name

English

ETHYL SALICYLATE [FCC]

Common Name

English

ETHYL 2-HYDROXYBENZOATE

Systematic Name

English

SAL ETHYL

Common Name

English

NSC-8209

Code

English

FEMA NO. 2458

Code

English

2-HYDROXYBENZOIC ACID ETHYL ESTER

Systematic Name

English

MESOTOL

Common Name

English

ETHYL SALICYLATE [FHFI]

Common Name

English

BENZOIC ACID, 2-HYDROXY-, ETHYL ESTER

Common Name

English

SALICYLIC ACID, ETHYL ESTER

Common Name

English

Ethyl salicylate [WHO-DD]

Common Name

English

ETHYL SALICYLATE [MART.]

Common Name

English

ETHYL SALICYLATE [MI]

Common Name

English

ETHYL O-HYDROXYBENZOATE

Common Name

English

METHYL SALICYLATE IMPURITY F [EP IMPURITY]

Common Name

English

2-ETHOXYCARBONYLPHENOL

Systematic Name

English

Classification Tree Code System Code

JECFA EVALUATION

ETHYL SALICYLATE