Salicylic acid

US Approved OTC

First marketed in 1860

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H6O3
Molecular Weight	138.1207
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=C(O)C=CC=C1

InChI

InChIKey=YGSDEFSMJLZEOE-UHFFFAOYSA-N

InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)

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

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-1 125 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8228
Cyclooxygenase-2 192 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 8228
High mobility group protein B1 13 Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955	Inhibitor 8228	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 8360	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 8360	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 8360	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 8360	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 83 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Approved 8360	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 8360	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 8360	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 1709	substrate 1010	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 688 CYP2C19 985 CYP2E1 648 CYP2A6 523 CYP2B6 660 UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 290 UGT2B4 249 UGT2B7 389 UGT2B15 203 UGT2B17 213	CYP2E1 126

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 964	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/	yes

Drug as victim

Target	Modality	Activity
CYP2A6 523	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2B6 660	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2E1 648	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	major
UGT1A4 347	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B15 203	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B17 213	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
CYP2C19 985	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C8 688	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C9 1010	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP3A4 1709	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
UGT1A1 418	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A10 290	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A3 422	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A6 307	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A7 236	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A8 283	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A9 380	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B4 249	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B7 389	substrate 3326 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
In vitro release studies of methyl salicylate from the ointment bases and the commercial dermatological products.	1990	2371308
[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
Hydroxyl radical adduct of 5-aminosalicylic acid: a potential marker of ozone-induced oxidative stress.	2001	11235916
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
Arabidopsis genome sequence as a tool for functional genomics in tomato.	2001	11178283
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
Nucleotide sequence analysis of 5'-flanking region of salicylate hydroxylase gene, and identification and purification of a LysR-type regulator, SalR.	2001 Apr	11298739
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
Hereditary palmoplantar keratoderma (four cases in three generations).	2001 Feb	11328395
Non-ionic micellar affinity capillary electrophoresis for analysis of interactions between micelles and drugs.	2001 Feb	11272320
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
Ethylene-dependent salicylic acid regulates an expanded cell death response to a plant pathogen.	2001 Feb	11208023
Breakage and fusion of the TEL (ETV6) gene in immature B lymphocytes induced by apoptogenic signals.	2001 Feb 1	11157492
Molecular cloning of the nahG gene encoding salicylate hydroxylase from Pseudomonas fluorescens.	2001 Feb 28	11266111
Effect of jasmonic, salicylic, and abscisic acids on [(14)C]leucine incorporation into proteins of pea leaves.	2001 Jan	11240395
Increases in the mutation frequency at which fusidic acid-resistant Staphylococcus aureus arise with salicylate.	2001 Jan	11192496
Guidelines for the management of cutaneous warts.	2001 Jan	11167676
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
The possibility of achieving an interactive mixture with high dose homogeneity containing an extremely low proportion of a micronised drug.	2001 Jan	11113648
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
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
Pathogen-induced expression of plant ATP: citrate lyase.	2001 Jan 19	11271173
Characterization of a rice (Oryza sativa L.) Bowman-Birk proteinase inhibitor: tightly light regulated induction in response to cut, jasmonic acid, ethylene and protein phosphatase 2A inhibitors.	2001 Jan 24	11223257
Synthesis and metal binding properties of salicylate-, catecholate-, and hydroxypyridinonate-functionalized dendrimers.	2001 Jan 5	11205020
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
Signaling mediated by the closely related mammalian Rho family GTPases TC10 and Cdc42 suggests distinct functional pathways.	2001 Mar	11306516
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
Interference by bilirubin in salicylate measurement.	2001 Mar	11269759
Quantitative analysis of analgoantipyretics in dosage form using planar chromatography.	2001 Mar	11248516
Potentiometric determination of acetylsalicylic acid by sequential injection analysis (SIA) using a tubular salicylate-selective electrode.	2001 Mar	11248498
Selective inhibition of interleukin-4 gene expression in human T cells by aspirin.	2001 Mar 15	11238116
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
Measurement of free radical production by in vivo microdialysis during ischemia/reperfusion injury to skeletal muscle.	2001 May 1	11316577
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 `Wed Jul 05 22:44:14 UTC 2023` Edited by `admin` on `Wed Jul 05 22:44:14 UTC 2023`
Record UNII	O414PZ4LPZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Salicylic acid

Official Name

English

LAMIVUDINE IMPURITY C [EP IMPURITY]

Common Name

English

SALICYLIC ACID [USP-RS]

Common Name

English

2-HYDROXYBENZENECARBOXYLIC ACID

Systematic Name

English

COMPOUND W

Brand Name

English

SALICYLIC ACID [EP IMPURITY]

Common Name

English

SALICYLIC ACID [USP]

Common Name

English

SALICYLIC ACID [JAN]

Common Name

English

SALICYLIC ACID [VANDF]

Common Name

English

SALICYLIC ACID [INCI]

Common Name

English

DR. SCHOLL'S CALLUS REMOVERS

Brand Name

English

SALICYLICUM ACIDUM

Common Name

English

FEMA NO. 3985

Code

English

SALICYLIC ACID [USP MONOGRAPH]

Common Name

English

SALICYLIC ACID [MART.]

Common Name

English

SULFASALAZINE IMPURITY H [EP IMPURITY]

Common Name

English

SALICYLICUM ACIDUM [HPUS]

Common Name

English

SALICYLIC ACID [GREEN BOOK]

Common Name

English

SALICYLIC ACID [MI]

Common Name

English

ACETYLSALICYLIC ACID IMPURITY C [EP IMPURITY]

Common Name

English

SALICYLIC ACID [HSDB]

Common Name

English

NSC-180

Code

English

2-HYDROXYBENZOIC ACID [FHFI]

Common Name

English

CARBASALATE CALCIUM IMPURITY C [EP IMPURITY]

Common Name

English

Salicylic acid [WHO-DD]

Common Name

English

DL-LYSINE ACETYLSALICYLATE IMPURITY A [EP IMPURITY]

Common Name

English

2-HYDROXYBENZOIC ACID

Systematic Name

English

ACIDUM SALICYLICUM [WHO-IP LATIN]

Common Name

English

SALICYLIC ACID [EP MONOGRAPH]

Common Name

English

SALICYLIC ACID [WHO-IP]

Common Name

English

K-557

Code

English

MESALAZINE IMPURITY H [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 358.710