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

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
Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE).	1999 May	10366903
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
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
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
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
Isolation and preliminary characterization of the medium-chain fatty acid:CoA ligase responsible for activation of short- and medium-chain fatty acids in colonic mucosa from swine.	2001 Feb	11281196
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
A novel pH-sensitive membrane from chitosan--TEOS IPN; preparation and its drug permeation characteristics.	2001 Feb	11205435
3-Hydroxybenzoic acid as an internal standard for the high-pressure liquid chromatography quantitation of salicylic acid in plants.	2001 Feb 1	11161302
A hot pepper cDNA encoding a pathogenesis-related protein 4 is induced during the resistance response to tobacco mosaic virus.	2001 Feb 28	11266114
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
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
Effect of 4-trifluoromethyl derivatives of salicylate on nuclear factor kappaB-dependent transcription in human astrocytoma cells.	2001 Jan	11159705
The possibility of achieving an interactive mixture with high dose homogeneity containing an extremely low proportion of a micronised drug.	2001 Jan	11113648
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
Pathogen-induced expression of plant ATP: citrate lyase.	2001 Jan 19	11271173
Synthesis and metal binding properties of salicylate-, catecholate-, and hydroxypyridinonate-functionalized dendrimers.	2001 Jan 5	11205020
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
Signaling mediated by the closely related mammalian Rho family GTPases TC10 and Cdc42 suggests distinct functional pathways.	2001 Mar	11306516
Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs.	2001 Mar	11256485
In vivo evidence for accelerated generation of hydroxyl radicals in liver of Long-Evans Cinnamon (LEC) rats with acute hepatitis.	2001 Mar 1	11182525
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
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
Binding of cosalane--a novel highly lipophilic anti-HIV agent--to albumin and glycoprotein.	2001 May	11288110
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

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

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CFR

21 CFR 333.310

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NCI_THESAURUS

C257

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NCI_THESAURUS

C52588

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CFR

21 CFR 358.510

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WHO-VATC

QD01AE12

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CFR

21 CFR 862.3830

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EPA PESTICIDE CODE

76602

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CFR

21 CFR 358.720

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WHO-VATC

QS01BC08

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WHO-ATC

S01BC08

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CFR

21 CFR 358.110

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FDA ORPHAN DRUG

359211

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WHO-VATC

QM02AC99

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JECFA EVALUATION

2-HYDROXYBENZOIC ACID

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WHO-ATC

D01AE12

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WHO-ESSENTIAL MEDICINES LIST

13.4

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Code System Code Type Description

RXCUI

9525

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JECFA MONOGRAPH

891

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HSDB

672

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FDA UNII

O414PZ4LPZ

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PUBCHEM

338

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RXCUI

9522

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ALTERNATIVE

RS_ITEM_NUM

1609002

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LACTMED

Salicylic Acid

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EVMPD

SUB15180MIG

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WIKIPEDIA

SALICYLIC ACID

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CAS

69-72-7

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WIKIPEDIA

Medical uses of salicylic acid

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ECHA (EC/EINECS)

200-712-3

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MESH

D020156

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CHEBI

30762

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IUPHAR

4306

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NSC

180

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SMS_ID

100000090038

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DRUG CENTRAL

2416

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CHEBI

16914

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DAILYMED

O414PZ4LPZ

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MERCK INDEX

m9739

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Merck Index

NCI_THESAURUS

C61934

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WHO INTERNATIONAL PHARMACOPEIA

SALICYLIC ACID

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PRIMARY

Description: Colourless crystals, usually needle-like, or a white, crystalline powder; odourless. Solubility: Slightly soluble in water; soluble in 4 parts of ethanol (~750 g/l) TS and in 3 parts of ether R. Category: Keratolytic. Storage: Salicylic acid should be kept in a well-closed container. Definition: Salicylic acid contains not less than 99.0% and not more than 101.0% of C7H6O3, calculated with reference to the dried substance.

ChEMBL

CHEMBL424

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DRUG BANK

DB00936

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EPA CompTox

DTXSID7026368

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