BENZYL SALICYLATE

US Approved OTC

First marketed in 1860

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12O3
Molecular Weight	228.2433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(C=CC=C1)C(=O)OCC2=CC=CC=C2

InChI

InChIKey=ZCTQGTTXIYCGGC-UHFFFAOYSA-N

InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2

HIDE SMILES / InChI

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 2008
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 2008
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 2008
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 2008
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 2012
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 2012
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 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 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
Arabidopsis genome sequence as a tool for functional genomics in tomato.	2001	11178283
Unraveling regulatory networks in plant defense using microarrays.	2001	11178281
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
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
Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay.	2001 Feb	11266322
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
Probenazole induces systemic acquired resistance in Arabidopsis with a novel type of action.	2001 Jan	11169191
The possibility of achieving an interactive mixture with high dose homogeneity containing an extremely low proportion of a micronised drug.	2001 Jan	11113648
Induction of cell death in arabidopsis by superoxide in combination with salicylic acid or with protein synthesis inhibitors.	2001 Jan 1	11134900
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
A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus.	2001 Jul 6	11306574
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
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
Identification of free radicals produced during phacoemulsification.	2001 Mar	11255062
Action of 2,3-butanedione monoxime on capacitance and electromotility of guinea-pig cochlear outer hair cells.	2001 Mar 15	11251049
Microdialysis of salicylic acid from viscous emulsion samples prior to high-performance liquid chromatographic determination.	2001 Mar 30	11307985
Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection.	2001 Mar 5	11254191
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

Name

Type

Language

BENZYL SALICYLATE

Official Name

English

BENZYL SALICYLATE [FCC]

Common Name

English

BENZYL SALICYLATE [MI]

Common Name

English

FEMA NO. 2151

Code

English

BENZYL 2-HYDROXYBENZOATE

Systematic Name

English

BENZYL SALICYLATE [FHFI]

Common Name

English

BENZYL SALICYLATE [INCI]

Common Name

English

BENZYL O-HYDROXYBENZOATE

Common Name

English

Benzyl salicylate [WHO-DD]

Common Name

English

2-HYDROXYBENZOIC ACID PHENYLMETHYL ESTER

Systematic Name

English

NSC-6647

Code

English

SALICYLIC ACID BENZYL ESTER

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 172.515