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=C(S)C=CC=C1

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 8297

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 504	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 504	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 504	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 504	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
Thimerosal in the detection of clinically relevant allergic contact reactions.	2001 Jul	11423830
Simultaneous determination of reduced and oxidized glutathione in peripheral blood mononuclear cells by liquid chromatography-electrospray mass spectrometry.	2001 Jun 5	11419750
Superoxide dismutase activity and electrochemical study of the binuclear [Cu(TSA)2py]2 complex.	2002	12437156
Preconcentration of lead with Amberlite XAD-2 and Amberlite XAD-7 based chelating resins for its determination by flame atomic absorption spectrometry.	2002 Mar 11	18968550
Antimycobacterial and antifungal isosters of salicylamides.	2003 Aug	12953220
The thiol reagent, thimerosal, irreversibly inhibits meiosis reinitiation in mouse oocyte when applied during a very early and narrow temporal window: a pharmacological analysis.	2003 Aug	12840819
Increase in peripheral benzodiazepine receptors and loss of glutamate NMDA receptors in a mouse model of closed head injury: a quantitative autoradiographic study.	2003 Dec	14683703
A new LC/MS-method for the quantitation of acrylamide based on a stable isotope dilution assay and derivatization with 2-mercaptobenzoic acid. Comparison with two GC/MS methods.	2003 Dec 31	14690366
An alternative synthesis of 2-(N-arylhydrazono)-1-benzothiophen-3-ones.	2003 Mar 7	12929366
Zn(II)-catalyzed thiolysis of oxiranes in water under neutral conditions.	2003 Oct 17	14535811
Effect of taxol and okadaic acid on microtubule dynamics in thimerosal-arrested primary mouse oocytes: a confocal study.	2003 Sep	14519558
Lactic acid triggers, in vitro, thiomersal to degrade protein in the presence of PLGA microspheres.	2004 Apr 1	15010124
Development of a direct-binding chloramphenicol sensor based on thiol or sulfide mediated self-assembled antibody monolayers.	2004 Feb 15	14709384
Using model complexes to augment and advance metalloproteinase inhibitor design.	2004 May 17	15132609
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 Dec 23	16187379
Determination of mercury complexation in coastal and estuarine waters using competitive ligand exchange method.	2005 Sep 1	16190218
Uncoupling of ATP-mediated calcium signaling and dysregulated interleukin-6 secretion in dendritic cells by nanomolar thimerosal.	2006 Jul	16835063
Effect of subinhibitory concentration of some established and experimental antifungal compounds on the germ tube formation in Candida albicans.	2007	17571794
Competing ligand exchange-solid phase extraction method for the determination of the complexation of dissolved inorganic mercury (II) in natural waters.	2007 Aug 29	17719908
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 Jul 27	17960073
Relationship between redox activity and chemical speciation of size-fractionated particulate matter.	2007 Jun 7	17555562
Determination of acrylamide during roasting of coffee.	2008 Aug 13	18624446
Development of a stable isotope dilution assay for the quantitation of glycidamide and its application to foods and model systems.	2008 Aug 13	18624425
Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis.	2008 Jan 10	17888894
Thimerosal and the relevance of patch-test reactions in children.	2008 Sep-Oct	18845117
[1,2-Bis(diphenyl-phosphino)ethane-κP,P'](2-carboxyl-atothio-phenolato-κO,S)nickel(II) methanol solvate.	2009 Jan 8	21581768
Mercury exposure, nutritional deficiencies and metabolic disruptions may affect learning in children.	2009 Oct 27	19860886
Field-assisted synthesis of SERS-active silver nanoparticles using conducting polymers.	2010 Aug	20820731
Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives.	2010 Jul	20417223
Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling.	2010 Jul-Aug	20457211
Poly[(dimethyl-formamide)(μ(4)-2,2'-sulfanediyldibenzoato)nickel(II)].	2010 Mar 6	21580481
2-[(2-Carboxy-phen-yl)disulfan-yl]benzoic acid-4,4'-bipyridyl N,N'-dioxide (1/2).	2010 May 26	21579515
14-(1,3-Benzodioxol-5-yl)-7,14-dihydro-dibenzo[a,j]acridine.	2010 Nov 6	21589382

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 `Fri Dec 15 15:17:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:17:19 GMT 2023`
Record UNII	CIP6LXN5XW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOSALICYLIC ACID

Official 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

THIOSALICYLIC ACID [INCI]

Common Name

English

NSC-2184

Code

English

2-THIOSALICYLIC ACID [HSDB]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

78903

Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023

NCI_THESAURUS

C257

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

Code System Code Type Description

NSC

660640

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

PRIMARY

WIKIPEDIA

THIOSALICYLIC ACID

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

PRIMARY

MESH

C441201

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

PRIMARY

NSC

2184

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

PRIMARY

PUBCHEM

5443

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

PRIMARY

RXCUI

322165

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

PRIMARY

EPA CompTox

DTXSID4049032

Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023

PRIMARY

CHEBI

59124

Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023

PRIMARY

RXCUI

91099

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

ALTERNATIVE

FDA UNII

CIP6LXN5XW

Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023

PRIMARY

CHEBI

59127

Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023

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MERCK INDEX

m10783

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

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Merck Index

CAS

147-93-3

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PRIMARY

HSDB

2739

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

PRIMARY

DRUG BANK

DB14026

Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023

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NCI_THESAURUS

C87327

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

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SMS_ID

100000183747

Created by admin on Fri Dec 15 15:17:20 GMT 2023 , Edited by admin on Fri Dec 15 15:17:20 GMT 2023

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ECHA (EC/EINECS)

205-704-3

Created by admin on Fri Dec 15 15:17:19 GMT 2023 , Edited by admin on Fri Dec 15 15:17:19 GMT 2023

PRIMARY

Related Record Type Details


					C2D9ITW04B

SODIUM THIOSALICYLATE

SALT/SOLVATE -> PARENT

Related Record Type Details


					2225PI3MOV

THIMEROSAL

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

Related Record Type Details


					CIP6LXN5XW

THIOSALICYLIC ACID

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: 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

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

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