U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C3H7O3S3.Na.H2O
Molecular Weight 228.286
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM 2,3-DIMERCAPTO-1-PROPANESULFONATE MONOHYDRATE

SMILES

O.[Na+].[O-]S(=O)(=O)CC(S)CS

InChI

InChIKey=XMUHNMQFDVIWGU-UHFFFAOYSA-M
InChI=1S/C3H8O3S3.Na.H2O/c4-9(5,6)2-3(8)1-7;;/h3,7-8H,1-2H2,(H,4,5,6);;1H2/q;+1;/p-1

HIDE SMILES / InChI

Molecular Formula C3H8O3S3
Molecular Weight 188.289
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Unithiol was developed in the Soviet Union in the late 1950s. It only became more widely used in America and Western Europe since the mid-1970s, and particularly since the late 1970s when the Heyl Company in Germany began production. It remained the mainstay of chelation treatment of arsenic and mercury intoxication for more than half a century. Unithiol has been used in the management of acute and chronic poisoning with a number of different metals and metalloids, and is particularly useful for arsenic, bismuth and mercury. Unithiol can be given parenterally or orally depending on the clinical situation and severity of poisoning. Its action mechanism is close that of complexones. Active sulfhydryl groups enter into reactions with thiol poisons present in blood and tissues, form not toxic complex with them eliminated with urine. The poisons fixation results in the body enzyme systems changed under the poisons effect functions restoration. It is efficient as an antidote in case of intoxications by arsenic and heavy metals salts.

CNS Activity

Curator's Comment: DMPS can cross the blood–brain barrier of mice, but not that of humans, limiting its use to extracting heavy metals from parts of the body other than the central nervous system.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIMAVAL

Approved Use

Dimaval is used for cases of acute mercury poisoning (metallic, vapour, inorganic or organic compounds), if application by mouth or treatment by means of a gastric aspiration tube are not possible.
PubMed

PubMed

TitleDatePubMed
Inhibition of NF-kappa B activation by arsenite through reaction with a critical cysteine in the activation loop of Ikappa B kinase.
2000 Nov 17
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
2001 Nov
The renal Na(+)-dependent dicarboxylate transporter, NaDC-3, translocates dimethyl- and disulfhydryl-compounds and contributes to renal heavy metal detoxification.
2002 Nov
Purine nucleoside phosphorylase as a cytosolic arsenate reductase.
2002 Nov
Lead-induced oxidative stress and hematological alterations and their response to combined administration of calcium disodium EDTA with a thiol chelator in rats.
2004
2,3-Dimercaptopropanol, 2,3-dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid acute administration diferentially change biochemical parameters in mice.
2005 Apr
Efficacy of 2,3-dimercapto-1-propanesulfonic acid (DMPS) and diphenyl diselenide on cadmium induced testicular damage in mice.
2005 Dec
Arsenic induced blood and brain oxidative stress and its response to some thiol chelators in rats.
2005 Sep 16
Effects of BSO, GSH, Vit-C and DMPS on the nephrotoxicity of mercury.
2007 Aug
Effects of 2,3-dimercapto-1-propanesulfonic acid (DMPS) on methylmercury-induced locomotor deficits and cerebellar toxicity in mice.
2007 Oct 8
Multidrug resistance proteins and the renal elimination of inorganic mercury mediated by 2,3-dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid.
2008 Jan
MRP2 and the DMPS- and DMSA-mediated elimination of mercury in TR(-) and control rats exposed to thiol S-conjugates of inorganic mercury.
2008 Sep
[Oxidative stress of acute paraquat poisoned rats and sodium dimercaptopropane sulfonate intervention].
2009 Aug
[Expression of thrombomodulin, endothelial protein C receptor in lung tissue of acute paraquat poisoned rats and intervention of sodium dimercaptopropane sulfonate].
2009 Aug
Mechanism of thiol-supported arsenate reduction mediated by phosphorolytic-arsenolytic enzymes: I. The role of arsenolysis.
2009 Aug
MRP2 involvement in renal proximal tubular elimination of methylmercury mediated by DMPS or DMSA.
2009 Feb 15
[Expression of angiotensin converting enzyme and angiotensin converting enzyme 2 gene in lung of paraquat poisoning rats and protection of sodium dimercaptopropane sulfonate].
2010 Apr
Effects of selenite and chelating agents on mammalian thioredoxin reductase inhibited by mercury: implications for treatment of mercury poisoning.
2011 Jan
Effects of co-administration of dietary sodium arsenate and 2,3-dimercaptopropane-1-sulfonic acid (DMPS) on the rat bladder epithelium.
2012 Sep 28
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: can also be used orally https://www.ncbi.nlm.nih.gov/pubmed/12711426
For managing acute and chronic intoxications by arsenic and mercury compounds utnithiol is injected intramuscular or subcutaneous (5 – 10 ml of 5% solution). The treatment should be started as early as possible. In case of intoxications by arsenic compounds injections are every 6 – 8 hours the first day, 2 – 3 injections every 8 – 12 hours the second day, 1 – 2 injections the subsequent days. Children are made intramuscular injections in the doses 1 ml of 5% solution for each 10 kg of the body mass every 6 hours the first day; then 1 – 3 injections a day. In case of intoxications by mercury salts the preparation is injected for not less than 6 days. In case of intoxications by cardiac glicosides it is injected intramuscular or subcutaneous in the dose 5 or 10 ml of the unithiol 5% solution during the first 2 days. Injections are made 3 – 4 times a day. Then it is injected 1 – 2 times a day until the cardiotoxic action stops. In case of hepatocerebral degeneration 5 – 10 ml of the unithiol solution is prescribed for daily or in a day intramuscular injections, the course being 25 – 30 injections with an interval between the courses – 3 – 4 months. In case of diabetic polyneuropathy 5 ml of 5% solution is injected for 10 days. In case of chronic alcoholism the preparation is introduced intramuscular in dose 3 – 5 ml of 5% solution 2 – 3 times a week. For arresting the alcoholic delirium attacks 4 – 5ml of 5% solution is injected intramuscular. 1 ml of the preparation contains 50 mg of unithiol.
Route of Administration: Other
When HepG2 cells were co-treated with As3+ (25 uM) and DMPS (Unithiol) (0.02, 0.2, 1.0, or 2.0 mM), cellular arsenic was decreased with the increasing of DMPS concentration from 0.02 mM to 2.0 mM. DMPS at high concentration (>1.0 mM) dramatically decreased the accumulation of arsenic in HepG2 cells. The cellular arsenic was decreased from 5.72% to 0.13% when the cells were treated with 2.0 mM DMPS.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:25:38 GMT 2023
Edited
by admin
on Sat Dec 16 08:25:38 GMT 2023
Record UNII
DH52SRB8Z2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM 2,3-DIMERCAPTO-1-PROPANESULFONATE MONOHYDRATE
Systematic Name English
1-PROPANESULFONIC ACID, 2,3-DIMERCAPTO-, SODIUM SALT, HYDRATE (1:1:1)
Systematic Name English
SODIUM 2,3-DIMERCAPTOPROPANESULFONATE HYDRATE
Systematic Name English
UNITHIOL MONOHYDRATE
Common Name English
SODIUM 2,3-DIMERCAPTOPROPANE SULFONATE MONOHYDRATE
Systematic Name English
1-PROPANESULFONIC ACID, 2,3-DIMERCAPTO-, MONOSODIUM SALT, MONOHYDRATE
Systematic Name English
Code System Code Type Description
FDA UNII
DH52SRB8Z2
Created by admin on Sat Dec 16 08:25:38 GMT 2023 , Edited by admin on Sat Dec 16 08:25:38 GMT 2023
PRIMARY
PUBCHEM
23676755
Created by admin on Sat Dec 16 08:25:38 GMT 2023 , Edited by admin on Sat Dec 16 08:25:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID9046607
Created by admin on Sat Dec 16 08:25:38 GMT 2023 , Edited by admin on Sat Dec 16 08:25:38 GMT 2023
PRIMARY
CAS
207233-91-8
Created by admin on Sat Dec 16 08:25:38 GMT 2023 , Edited by admin on Sat Dec 16 08:25:38 GMT 2023
PRIMARY
SMS_ID
100000164807
Created by admin on Sat Dec 16 08:25:38 GMT 2023 , Edited by admin on Sat Dec 16 08:25:38 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY