THIOSALICYLIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H6O2S
Molecular Weight	154.186
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=CC=C1S

InChI

InChIKey=NBOMNTLFRHMDEZ-UHFFFAOYSA-N

InChI=1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9)

HIDE SMILES / InChI

Molecular Formula	C7H6O2S
Molecular Weight	154.186
Charge	0
Count

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

Description
Sources: ISBN: 978-0-7637-6547-7, 'Nurse's Drug 2009' (2009), p. 949, Retrieved from https://books.google.com/books?id=pobp8JRNW1MC&pg | https://www.ncbi.nlm.nih.gov/pubmed/13563950

Thiosalicylic acid is an analgesic and anti-inflammatory agent. It is used (in form of sodium salt) to relieve symptoms of acute gout, painful musculoskeletal conditions, osteoarthritis and rheumatic fever. The drug exerts its action by inhibiting prostaglandin synthesis. Thiosalicylic acid usage is associated with the risk of contact dermatitis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
prostaglandin biosynthetic process 23 Target ID: GO:0001516 Sources: ISBN: 978-0-7637-6547-7, 'Nurse's Drug 2009' (2009), p. 949, Retrieved from https://books.google.com/books?id=pobp8JRNW1MC&pg	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Acute gout 3 Sources: (2009) 'Nurse's Drug 2009', p. 949, retrieved from: https://books.google.com/books?id=pobp8JRNW1MC&pg	Palliative	Not Provided 511	REXOLATE Approved Use To relieve symptoms of acute gout, to relieve pain from musculoskeletal conditions, to relieve symptoms of osteoarthritis, to treat rheumatic fever.
Musculoskeletal conditions 6 Sources: (2009) 'Nurse's Drug 2009', p. 949, retrieved from: https://books.google.com/books?id=pobp8JRNW1MC&pg	Palliative	Not Provided 511	REXOLATE Approved Use To relieve symptoms of acute gout, to relieve pain from musculoskeletal conditions, to relieve symptoms of osteoarthritis, to treat rheumatic fever.
Osteoarthritis 157 Sources: (2009) 'Nurse's Drug 2009', p. 949, retrieved from: https://books.google.com/books?id=pobp8JRNW1MC&pg	Palliative	Not Provided 511	REXOLATE Approved Use To relieve symptoms of acute gout, to relieve pain from musculoskeletal conditions, to relieve symptoms of osteoarthritis, to treat rheumatic fever.
Rheumatic fever 6 Sources: (2009) 'Nurse's Drug 2009', p. 949, retrieved from: https://books.google.com/books?id=pobp8JRNW1MC&pg	Primary	Not Provided 511	REXOLATE Approved Use To relieve symptoms of acute gout, to relieve pain from musculoskeletal conditions, to relieve symptoms of osteoarthritis, to treat rheumatic fever.

PubMed

Title	Date	PubMed
Luteolin and thiosalicylate inhibit HgCl(2) and thimerosal-induced VEGF release from human mast cells.	2011-01-20	21244751
14-(1,3-Benzodioxol-5-yl)-7,14-dihydro-dibenzo[a,j]acridine.	2010-11-06	21589382
Ultraviolet treatment and biodegradation of dibenzothiophene: Identification and toxicity of products.	2010-11	20862751
Low molecular weight thiols reduce thimerosal neurotoxicity in vitro: modulation by proteins.	2010-10-29	20696200
Field-assisted synthesis of SERS-active silver nanoparticles using conducting polymers.	2010-08	20820731
Intercalation of anionic organic ultraviolet ray absorbers into layered zinc hydroxide nitrate.	2010-07-01	20378120
Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives.	2010-07	20417223
2-[(2-Carboxy-phen-yl)disulfan-yl]benzoic acid-4,4'-bipyridyl N,N'-dioxide (1/2).	2010-05-26	21579515
Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling.	2010-03-17	20457211
Poly[(dimethyl-formamide)(μ(4)-2,2'-sulfanediyldibenzoato)nickel(II)].	2010-03-06	21580481
Electrochemical scanning tunneling spectroscopy of redox-active molecules bound by Au-C bonds.	2010-03-03	19954234
Phase 1 first-in-human clinical study of S-trans,trans-farnesylthiosalicylic acid (salirasib) in patients with solid tumors.	2010-01	19484470
Mercury exposure, nutritional deficiencies and metabolic disruptions may affect learning in children.	2009-10-27	19860886
Synthesis and characterization of thiosalicylic acid stabilized gold nanoparticles.	2009-09-15	19577955
2-[(2-Carboxy-phen-yl)sulfan-yl]acetic acid.	2009-09-05	21577786
The Ras inhibitor farnesylthiosalicyclic acid (FTS) prevents nodule formation and development of preneoplastic foci of altered hepatocytes in rats.	2009-07	19427195
Expression of metallothionein mRNAs on mouse cerebellum microglia cells by thimerosal and its metabolites.	2009-06-30	19386279
Ultrasonic-assisted precolumn derivatization-HPLC determination of acrylamide formed in Radix Asparagi during heating process.	2009-05-01	19269121
Zinc ions cause the thimerosal-induced signal of fluorescent calcium probes in lymphocytes.	2009-02	18977527
[1,2-Bis(diphenyl-phosphino)ethane-κP,P'](2-carboxyl-atothio-phenolato-κO,S)nickel(II) methanol solvate.	2009-01-08	21581768
Thimerosal and the relevance of patch-test reactions in children.	2008-10-11	18845117
Determination of acrylamide during roasting of coffee.	2008-08-13	18624446
Development of a stable isotope dilution assay for the quantitation of glycidamide and its application to foods and model systems.	2008-08-13	18624425
Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries.	2008-08	18663392
In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols.	2008-04-30	18321603
Removal of malodorous organic sulfides with molecular oxygen and visible light over metal phthalocyanine.	2008-03-21	17707582
Synthesis and biological evaluation of sulfur-containing cinnamate and salicylate derivatives.	2008-03	18310951
Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis.	2008-01-10	17888894
Competing ligand exchange-solid phase extraction method for the determination of the complexation of dissolved inorganic mercury (II) in natural waters.	2007-08-29	17719908
Field amplified sample injection-capillary electrophoresis-tandem mass spectrometry for the analysis of acrylamide in foodstuffs.	2007-08-03	17383666
Heterocycles [h]fused onto 4-oxoquinoline-3-carboxylic acid, part IV. Convenient synthesis of substituted hexahydro [1,4]thiazepino[2,3-h]quinoline-9-carboxylic acid and its tetrahydroquino[7,8-b]benzothiazepine homolog.	2007-07-27	17960073
Relationship between redox activity and chemical speciation of size-fractionated particulate matter.	2007-06-07	17555562
Effect of subinhibitory concentration of some established and experimental antifungal compounds on the germ tube formation in Candida albicans.	2007	17571794
Effect of ring substitution position on the structural conformation of mercaptobenzoic acid self-assembled monolayers on Au(111).	2006-12-19	17154594
Analysis of acrylamide in food products by in-line preconcentration capillary zone electrophoresis.	2006-09-29	16843477
Thimerosal induces apoptosis and G2/M phase arrest in human leukemia cells.	2006-09	16649253
Analysis of acrylamide in food samples by capillary zone electrophoresis.	2006-07-07	16310205
Uncoupling of ATP-mediated calcium signaling and dysregulated interleukin-6 secretion in dendritic cells by nanomolar thimerosal.	2006-07	16835063
Self-assembly of dialkyltin moieties and mercaptobenzoic acid into macrocyclic complexes with hydrophobic "pseudo-cage" or double-cavity structures: supramolecular infrastructures involving intermolecular C-H...S weak hydrogen bonds and pi-pi interactions.	2005-12-23	16187379
Determination of mercury complexation in coastal and estuarine waters using competitive ligand exchange method.	2005-09-01	16190218
Quantitative description of the deactivation channels of the first excited singlet state of 2- and 4-thiosalicylic acids.	2005-07-28	16833990
Chelating sorbents based on silica gel and their application in atomic spectrometry.	2005-03	15703917
One-pot synthesis of benzo[e]1,4-oxathiepin-5-ones under solvent-free condition via self-promoted thiolysis of 1,2-epoxides.	2004-12-10	15575757
Determination of thiocyl in biological samples by liquid chromatography with ThioGlo 3 derivatization.	2004-10-05	15315779
A new positron emission tomography imaging agent for the serotonin transporter: synthesis, pharmacological characterization, and kinetic analysis of [11C]2-[2-(dimethylaminomethyl)phenylthio]-5-fluoromethylphenylamine ([11C]AFM).	2004-07	15219271
Using model complexes to augment and advance metalloproteinase inhibitor design.	2004-05-17	15132609
Lactic acid triggers, in vitro, thiomersal to degrade protein in the presence of PLGA microspheres.	2004-04-01	15010124
Development of a direct-binding chloramphenicol sensor based on thiol or sulfide mediated self-assembled antibody monolayers.	2004-02-15	14709384
Preconcentration of lead with Amberlite XAD-2 and Amberlite XAD-7 based chelating resins for its determination by flame atomic absorption spectrometry.	2002-03-11	18968550
Cytotoxicity of Triorganophosphinegold(I) n-Mercaptobenzoates, n = 2, 3 and 4.	2002	18476010

Patents

Sample Use Guides

In Vivo Use Guide

Acute gout: initial dose is 100 mg every 3 to 4 hours for 2 days, then 100 mg daily. Painful musculoskeletal conditions: 50 to 100 mg daily or every other day. Osteoarthritis: 10 mg 3 times/week for several weeks then once a week, usually up to a total dosage of 2.5 g. Rheumatic fever: initial dose is 100 to 150 mg every 4 to 8 hours for 3 days, then 100 mg two times daily.

Route of Administration: Other

In Vitro Use Guide

Human platelets were incubated with thiosalicylic acid at 0.5 mM for 3 min in the presence of 1,2 and 1,3-glyceryl dinitrate. A concentration-dependent inhibition of platelet aggregation was observed.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:52:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:56 GMT 2025`
Record UNII	CIP6LXN5XW
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

THIOSALICYLIC ACID

Official Name

English

NSC-2184

Preferred Name

English

Thiosalicylic acid [WHO-DD]

Common Name

English

O-SULFHYDRYLBENZOIC ACID

Systematic Name

English

THIOSALICYLATE

Systematic Name

English

2-MERCAPTOBENZOIC ACID

Systematic Name

English

THIOSALICYLIC ACID [USP IMPURITY]

Common Name

English

THIOSALICYLIC ACID [MI]

Common Name

English

NSC-660640

Code

English

2-THIOSALICYLIC ACID [HSDB]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

78903