CHOLINE SALICYLATE

US Approved OTC

First marketed in 1860

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H5O3.C5H14NO
Molecular Weight	241.2836
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(C)CCO.OC1=C(C=CC=C1)C([O-])=O

InChI

InChIKey=UDKCHVLMFQVBAA-UHFFFAOYSA-M

InChI=1S/C7H6O3.C5H14NO/c8-6-4-2-1-3-5(6)7(9)10;1-6(2,3)4-5-7/h1-4,8H,(H,9,10);7H,4-5H2,1-3H3/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C7H6O3
Molecular Weight	138.1207
Charge	0
Count

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

Molecular Formula	C5H13NO
Molecular Weight	103.1628
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
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-1 131 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8504
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8504
High mobility group protein B1 13 Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955	Inhibitor 8504	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 8583	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 2008
Simple backache 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8583	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 2008
Arthritis 87 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8583	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 2008
Bruises 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative	Approved 8583	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 2008
Psoriasis 87 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8583	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 2012
Keratosis palmaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8583	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 2012
Ichthyosis vulgaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8583	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 2012

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 Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F 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 Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F 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 Health Status: unhealthy Age Group: 23.05 ± 5.7 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27904577/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 810 CYP2C19 1119 CYP2E1 729 CYP2A6 626 CYP2B6 776 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 UGT2B17 237	CYP2E1 131

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 1146	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/	yes

Drug as victim

Target	Modality	Activity
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	major
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B7 456	substrate 4014 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
eMolecules	478035	https://www.emolecules.com/cgi-bin/more?vid=478035
MolPort	MolPort-001-769-476	https://www.molport.com/shop/molecule-link/MolPort-001-769-476
ZINC	ZINC000000001554	http://zinc15.docking.org/substances/ZINC000000001554

PubMed

Title	Date	PubMed
Salicylate attenuates gentamicin-induced ototoxicity.	1999 Jul	10418821
Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE).	1999 May	10366903
Effects of salicylates on evoked otoacoustic emissions and remote masking in humans.	1999 May-Jun	10437688
Microdialysis vs. suction blister technique for in vivo sampling of pharmacokinetics in the human dermis.	1999 Sep	10494706
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.	2001	11296921
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Cyanide-resistant alternative respiration is strictly correlated to intracellular peroxide levels in Acremonium chrysogenum.	2001 Apr	11328676
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
Non-ionic micellar affinity capillary electrophoresis for analysis of interactions between micelles and drugs.	2001 Feb	11272320
Increased leukotriene production by food additives in patients with atopic dermatitis and proven food intolerance.	2001 Feb	11251628
Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction.	2001 Feb	11236213
The spinning disc reactor--studies on a novel TiO2 photocatalytic reactor.	2001 Feb	11100791
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
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
Guidelines for the management of cutaneous warts.	2001 Jan	11167676
Induction of cell death in arabidopsis by superoxide in combination with salicylic acid or with protein synthesis inhibitors.	2001 Jan 1	11134900
Reversed-phase high-performance liquid chromatography versus spectrophotometric assay for thimerosal in Cuban recombinant hepatitis B vaccine.	2001 Jan 12	11217023
Pathogen-induced expression of plant ATP: citrate lyase.	2001 Jan 19	11271173
Release of salicylic acid, diclofenac acid and diclofenac acid salts from isotropic and anisotropic nonionic surfactant systems across rat skin.	2001 Jan 5	11165822
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
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
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
Selective inhibition of interleukin-4 gene expression in human T cells by aspirin.	2001 Mar 15	11238116
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
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
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

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 `Mon Mar 31 17:36:33 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:33 GMT 2025`
Record UNII	KD510K1IQW
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BENZOIC ACID, 2-HYDROXY-, ION(1-), 2-HYDROXY-N,N,N-TRIMETHYLETHANAMINIUM

Preferred Name

English

CHOLINE SALICYLATE

Official Name

English

CHOLINE SALICYLATE [VANDF]

Common Name

English

(2-HYDROXYETHYL)TRIMETHYL AMMONIUM SALICYLATE

Systematic Name

English

CHOLINE SALICYLATE [MI]

Common Name

English

CHOLINE SUBSALICYLATE

Common Name

English

SALICYLIC ACID, ION(1-), CHOLINE

Common Name

English

CHOLINE SALICYLATE [USAN]

Common Name

English

CHOLINE SALICYLATE [MART.]

Common Name

English

SALICYLIC ACID CHOLINE SALT

Common Name

English

(2-HYDROXYETHYL)TRIMETHYLAMMONIUM 2-HYDROXYBENZOATE

Systematic Name

English

Choline salicylate [WHO-DD]

Common Name

English

CHOLINE SALICYLIC ACID SALT

Common Name

English

CHOLINE, SALICYLATE (SALT)

Common Name

English

ETHANAMINIUM, 2-HYDROXY-N,N,N-TRIMETHYL-, 2-HYDROXYBENZOATE (1:1)

Systematic Name

English

CHOLINE SALICYLATE [JAN]

Common Name

English

choline salicylate [INN]

Common Name

English

ETHANAMINIUM, 2-HYDROXY-N,N,N-TRIMETHYL-, SALT WITH 2-HYDROXYBENZOIC ACID (1:1)

Common Name

English

Classification Tree Code System Code

WHO-ATC

N02BA03