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Details

Stereochemistry ACHIRAL
Molecular Formula C2H3N3S2
Molecular Weight 133.1976
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5-AMINO-1,3,4-THIADIAZOLE-2-THIOL

SMILES

c1(=N)[nH]nc(S)s1

InChI

InChIKey=GDGIVSREGUOIJZ-UHFFFAOYSA-N
InChI=1S/C2H3N3S2/c3-1-4-5-2(6)7-1/h(H2,3,4)(H,5,6)

HIDE SMILES / InChI

Molecular Formula C2H3N3S2
Molecular Weight 133.1976
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25448967 | https://www.ncbi.nlm.nih.gov/pubmed/24494064 | https://www.ncbi.nlm.nih.gov/pubmed/18693019 | https://www.ncbi.nlm.nih.gov/pubmed/23093480

5-Amino-1,3,4-thiadiazole-2-thiol is a thiadiazole derivative with antibacterial activity used in the preparation of herbicides as well as carbonic anhydrase inhibitors.

Originator

Sources: Justus Liebigs Annalen der Chemie (1922), 426, 313-45.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.1 µM [Ki]
9.2 µM [Ki]
9.3 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity.
2001 Mar 15
Protease inhibitors: synthesis of matrix metalloproteinase and bacterial collagenase inhibitors incorporating 5-amino-2-mercapto-1,3,4-thiadiazole zinc binding functions.
2002 Oct 7
Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II, and IX with a series of 1,3,4-thiadiazole- and 1,2,4-triazole-thiols.
2005 May 2
QSAR analysis of some 5-amino-2-mercapto-1,3,4-thiadiazole based inhibitors of matrix metalloproteinases and bacterial collagenase.
2006 Jul 15
Polarized vibrational studies of bisguanidinium hydrogenphosphate monohydrate.
2006 May 1
Some features associated with organosilane groups grafted by the sol-gel process onto synthetic talc-like phyllosilicate.
2006 May 1
Synthesis, spectral and thermal studies of some organotin(IV) derivatives of 5-amino-3H-1,3,4-thiadiazole-2-thione.
2006 May 1
Neutral carriers based polymeric membrane electrodes for selective determination of mercury (II).
2007 May 2
Synthesis of mercaptothiadiazole-functionalized gold nanoparticles and their self-assembly on Au substrates.
2008 Feb 27
2-Amino-5-sulfanyl-1,3,4-thiadiazoles: a new series of selective cyclooxygenase-2 inhibitors.
2008 Sep
Syntheses and anti-depressant activity of 5-amino-1, 3, 4-thiadiazole-2-thiol imines and thiobenzyl derivatives.
2008 Sep 1
Selective electrochemical sensor for folic acid at physiological pH using ultrathin electropolymerized film of functionalized thiadiazole modified glassy carbon electrode.
2009 Aug 15
Simultaneous determination of epinephrine, uric acid and xanthine in the presence of ascorbic acid using an ultrathin polymer film of 5-amino-1,3,4-thiadiazole-2-thiol modified electrode.
2009 Aug 4
A one-dimensional cadmium(II) complex supported by a sulfur-nitro-gen mixed-donor ligand.
2009 Jun 27
Alkali-hydroxide-doped matrices for structural characterization of neutral underivatized oligosaccharides by MALDI time-of-flight mass spectrometry.
2009 Mar
Electropolymerized film of functionalized thiadiazole on glassy carbon electrode for the simultaneous determination of ascorbic acid, dopamine and uric acid.
2009 Nov
Immobilization of 5-amino-1,3,4-thiadiazole-thiol onto kanemite for thorium(IV) removal: thermodynamics and equilibrium study.
2009 Oct 1
Solvent-assisted slow conversion of a dithiazole derivative produces a competitive inhibitor of peptide deformylase.
2010 Apr
2,2'-Bi-1,3,4-thia-diazole-5,5'-diamine tetra-hydrate.
2010 Aug 4
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Applied Photophysics stopped-flow instrument has been used for measuring the initial velocities for the CO2 hydration reaction catalyzed by different CA isozymes, by following the change in absorbance of a pH indicator.Phenol red (at a concentration of 0.2 mM) has been used as indicator, working at the absorbance maximum of 557 nm, with 10 mM Hepes (pH 7.5) as buffer, 0.1 M Na2SO4 (for maintaining constant the ionic strength), following the CA-catalyzed CO2 hydration reaction for a period of 10–100 s.Saturated CO2 solutions in water at 20 C were used as the substrate. The CO2 concentrations ranged from 1.7 to 17 mM for the determination of the inhibition constants. For each inhibitor at least six traces of the initial 5–10% of the reaction have been used for determining the initial velocity. The uncatalyzed rates were determined in the same manner and subtracted from the total observed rates. The kinetic constants kcat and kcat/Km were obtained by non-linear least-squares methods using PRISM 3.Stock solutions of inhibitors (5-Amino-1,3,4-thiadiazole-2-thiol, compound 2) were prepared at a concentration of 1–3 mM (in DMSO–water 1:1, v/v) and dilutions up to 0.01 nM done with the assay buffer.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:55:31 UTC 2021
Edited
by admin
on Sat Jun 26 12:55:31 UTC 2021
Record UNII
B1HEG7V21S
Record Status Validated (UNII)
Record Version
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Name Type Language
5-AMINO-1,3,4-THIADIAZOLE-2-THIOL
Systematic Name English
1,3,4-THIADIAZOLE-2(3H)-THIONE, 5-AMINO-
Systematic Name English
WR-180
Code English
2-MERCAPTO-5-AMINO-1,3,4-THIADIAZOLE
Systematic Name English
2-AMINO-1,3,4-THIADIAZOL-5-THIOL
Systematic Name English
5-THIOL-2-AMINO-1,3,4-THIADIAZOLE
Common Name English
2-AMINO-.DELTA.2-1,3,4-THIADIAZOLINE-5-THIONE
Common Name English
2-AMINO-1,3,4-THIADIAZOLE-5-THIOL
Systematic Name English
2-AMINO-5-MERCAPTO-1,3,4-THIADIAZOLE
Systematic Name English
2-AMINO-5-MERCAPTOTHIADIAZOLE
Systematic Name English
.DELTA.2-1,3,4-THIADIAZOLINE-2-THIOL, 5-IMINO-
Common Name English
2-AMINO-5-MERCAPTO-1,3,5-THIADIAZOLE
Systematic Name English
5-AMINO-3H-1,3,4-THIADIZOLINE-2-THIONE
Common Name English
NSC-21402
Code English
NSC-209061
Code English
ATT
Common Name English
2-AMINO-1,3,4-THIADIAZOLE-5-MERCAPTAN
Common Name English
2-THIOL-5-AMINO-1,3,4-THIADIAZOLE
Common Name English
ACETAZOLAMIDE IMPURITY G [EP]
Common Name English
Code System Code Type Description
PUBCHEM
2723847
Created by admin on Sat Jun 26 12:55:31 UTC 2021 , Edited by admin on Sat Jun 26 12:55:31 UTC 2021
PRIMARY
CAS
2349-67-9
Created by admin on Sat Jun 26 12:55:31 UTC 2021 , Edited by admin on Sat Jun 26 12:55:31 UTC 2021
PRIMARY
EPA CompTox
2349-67-9
Created by admin on Sat Jun 26 12:55:31 UTC 2021 , Edited by admin on Sat Jun 26 12:55:31 UTC 2021
PRIMARY
FDA UNII
B1HEG7V21S
Created by admin on Sat Jun 26 12:55:31 UTC 2021 , Edited by admin on Sat Jun 26 12:55:31 UTC 2021
PRIMARY
DRUG BANK
DB12348
Created by admin on Sat Jun 26 12:55:31 UTC 2021 , Edited by admin on Sat Jun 26 12:55:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
219-078-4
Created by admin on Sat Jun 26 12:55:31 UTC 2021 , Edited by admin on Sat Jun 26 12:55:31 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP