SALICYLIC ACID

US Approved OTC

First marketed in 1860

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H6O3
Molecular Weight	138.121
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc(c(c1)C(=O)O)O

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	138.121
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	Condition	Potency
Cyclooxygenase-1 123 Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 7701	Psoriasis Keratosis palmaris Ichthyosis vulgaris
Cyclooxygenase-2 188 Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00936	Inhibitor 7701	Psoriasis Keratosis palmaris Ichthyosis vulgaris
High mobility group protein B1 13 Target ID: CHEMBL2311236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26101955	Inhibitor 7701	Psoriasis Keratosis palmaris Ichthyosis vulgaris	1.47999999999999998 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Strains and sprains 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative		Approved 7997	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 1203465600000
Simple backache 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative		Approved 7997	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 1203465600000
Arthritis 85 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative		Approved 7997	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 1203465600000
Bruises 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022029s003lbl.pdf	Palliative		Approved 7997	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 1203465600000
Psoriasis 79 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Cyclooxygenase-1 Cyclooxygenase-2 High mobility group protein B1	Approved 7997	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 1355011200000
Keratosis palmaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Cyclooxygenase-1 Cyclooxygenase-2 High mobility group protein B1	Approved 7997	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 1355011200000
Ichthyosis vulgaris 12 Sources: https://www.drugs.com/pro/salicylic-acid.html	Primary	Cyclooxygenase-1 Cyclooxygenase-2 High mobility group protein B1	Approved 7997	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 1355011200000

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 1470	substrate 865	substrate 1038

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 586 CYP2C19 830 CYP2E1 567 CYP2A6 452 CYP2B6 575 UGT1A1 358 UGT1A3 358 UGT1A4 295 UGT1A6 258 UGT1A7 197 UGT1A8 242 UGT1A9 327 UGT1A10 247 UGT2B4 213 UGT2B7 329 UGT2B15 165 UGT2B17 184	CYP2E1 116

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2E1 841	inducer 1333 Sources: https://pubmed.ncbi.nlm.nih.gov/9207195/	yes

Drug as victim

Target	Modality	Activity
CYP2A6 452	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2B6 575	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	likely
CYP2E1 567	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	major
UGT1A4 295	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B15 165	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
UGT2B17 184	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	no
CYP2C19 830	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C8 586	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2C9 865	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP2D6 1038	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
CYP3A4 1470	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/25840124/	yes
UGT1A1 358	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A10 247	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A3 358	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A6 258	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A7 197	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A8 242	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT1A9 327	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B4 213	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/16258079/	yes
UGT2B7 329	substrate 2752 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
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
False-high blood salicylate levels in neonates with hyperbilirubinemia.	2000 Dec	11128247
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
Unraveling regulatory networks in plant defense using microarrays.	2001	11178281
Comparison of the radical trapping ability of PBN, S-PPBN and NXY-059.	2001 Apr	11328677
[Principal constituents from flowering aerial parts of wild pansy].	2001 Apr	11320336
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
Nuclear factor-kappaB activation is not involved in a MPTP model of Parkinson's disease.	2001 Apr 17	11303744
Induction of wound response gene expression in tomato leaves by ionophores.	2001 Feb	11289608
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
A novel pH-sensitive membrane from chitosan--TEOS IPN; preparation and its drug permeation characteristics.	2001 Feb	11205435
Molecular responses to aphid feeding in Arabidopsis in relation to plant defense pathways.	2001 Feb	11161062
The arabidopsis ISR1 locus controlling rhizobacteria-mediated induced systemic resistance is involved in ethylene signaling.	2001 Feb	11161023
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
Effect of jasmonic, salicylic, and abscisic acids on [(14)C]leucine incorporation into proteins of pea leaves.	2001 Jan	11240395
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
Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP.	2001 Jan	11161607
A nuclear casein kinase 2 activity is involved in early events of transcriptional activation induced by salicylic acid in tobacco.	2001 Jan	11154347
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	11154344
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
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
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
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
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
Quantitative analysis of hydroxyl radicals in the anterior optic nerve of the cat following transient ischemia.	2001 Jan-Feb	11195744
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
Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs.	2001 Mar	11256485
Identification of free radicals produced during phacoemulsification.	2001 Mar	11255062
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
In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis.	2001 Mar 1	11182525
Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption.	2001 Mar 14	11250091
Action of 2,3-butanedione monoxime on capacitance and electromotility of guinea-pig cochlear outer hair cells.	2001 Mar 15	11251049
Flow-through UV spectrophotometric sensor for determination of (acetyl)salicylic acid in pharmaceutical preparations.	2001 Mar 23	11274811
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
Acanthoamoeba attachment to contact lenses.	2001 May	11320007
Measurement of free radical production by in vivo microdialysis during ischemia/reperfusion injury to skeletal muscle.	2001 May 1	11316577

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 Jun 25 21:14:17 UTC 2021` Edited by `admin` on `Fri Jun 25 21:14:17 UTC 2021`
Record UNII	O414PZ4LPZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SALICYLIC ACID

Official Name

English

MESALAZINE IMPURITY H [EP]

Common Name

English

SALICYLIC ACID [USP-RS]

Common Name

English

LAMIVUDINE RELATED COMPOUND SALICYLIC ACID [USP]

Common Name

English

2-HYDROXYBENZENECARBOXYLIC ACID

Systematic Name

English

COMPOUND W

Brand Name

English

SALICYLIC ACID [WHO-DD]

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 [MART.]

Common Name

English

SALICYLICUM ACIDUM [HPUS]

Common Name

English

SALICYLIC ACID [GREEN BOOK]

Common Name

English

SALICYLIC ACID [MI]

Common Name

English

SALICYLIC ACID [HSDB]

Common Name

English

SALICYLATE

Systematic Name

English

NSC-180

Code

English

2-HYDROXYBENZOIC ACID [FHFI]

Common Name

English

LAMIVUDINE IMPURITY C [EP]

Common Name

English

2-HYDROXYBENZOIC ACID

Systematic Name

English

ACIDUM SALICYLICUM [WHO-IP LATIN]

Common Name

English

SALICYLIC ACID RS [USP]

Common Name

English

SULFASALAZINE IMPURITY H [EP]

Common Name

English

SALICYLIC ACID [EP MONOGRAPH]

Common Name

English

LAMIVUDINE IMPURITY, SALICYLIC ACID- [USP]

Common Name

English

SALICYLIC ACID [WHO-IP]

Common Name

English

SALICYLIC ACID [USP]

Common Name

English

K-557

Code

English

SALICYLIC ACID [EP]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 358.710