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Details

Stereochemistry RACEMIC
Molecular Formula C4H7NO2S
Molecular Weight 133.169
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIMONACIC

SMILES

OC(=O)C1CSCN1

InChI

InChIKey=DZLNHFMRPBPULJ-UHFFFAOYSA-N
InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)

HIDE SMILES / InChI

Description

Timonacic or thioproline (4-Thiazolidinecarboxylic acid) is the product of condensation between cysteine and formaldehyde. Dietary timonacic slows the aging process in mammals and prolongs their life span. It exerts antioxidant and antineoplastic actions however its mechanism of action is elusive. Timonacic (brand names Heparegen or Arbitol) is used for the treatment of liver diseases.

CNS Activity

CNS Active
3913
Curator's Comment: Timonacic (thioproline) is CNS active in animals. No human data available.

Originator

Ratner, S.|Clarke, H.T.
8
Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/timonacic.html

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Heparegen

Approved Use

Heparegen (Timonacic) is used as a hepatoprotective agent
Primary
Approved
8429
Arbitol

Approved Use

Arbitol (Timonacic) is used as a hepatoprotective agent
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
New water-soluble prodrugs of HIV protease inhibitors based on O-->N intramolecular acyl migration.
2002 Dec
The amount of thiolic antioxidant ingestion needed to improve several immune functions is higher in aged than in adult mice.
2002 Feb
A diet supplemented with thiolic anti-oxidants improves leucocyte function in two strains of prematurely ageing mice.
2002 Nov
Formaldehyde scavenging from peritoneal dialysis solutions using reduced aminothiol compounds.
2004 Apr
Synthesis, calpain inhibitory activity, and cytotoxicity of P2-substituted proline and thiaproline peptidyl aldehydes and peptidyl alpha-ketoamides.
2006 Aug 24
Thioproline prevents carcinogenesis in the remnant stomach induced by duodenal reflux.
2006 Jun 18
Ingestion of thioproline suppresses rat esophageal adenocarcinogenesis caused by duodenogastroesophageal reflux.
2007 Dec
An expanded set of amino acid analogs for the ribosomal translation of unnatural peptides.
2007 Oct 3
Determination of thiazolidine-4-carboxylates in urine by chloroformate derivatization and gas chromatography-electron impact mass spectrometry.
2007 Sep
Investigation toward multi-epitope vaccine candidates using native chemical ligation.
2008
Lithium thiazolidine-4-carboxylate: synthesis, spectroscopic characterization and preliminary in vitro cytotoxic studies in human HeLa cells.
2008 Dec 1
Detection of endogenous DNA adducts, O-carboxymethyl-2'-deoxyguanosine and 3-ethanesulfonic acid-2'-deoxycytidine, in the rat stomach after duodenal reflux.
2008 Sep
An atom economic synthesis and antitubercular evaluation of novel spiro-cyclohexanones.
2009 Jul 1
Synthesis, structure and structure-activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents.
2009 Oct
A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation.
2010 Dec
A facile 1,3-dipolar cycloaddition of azomethine ylides to 2-arylidene-1,3-indanediones: synthesis of dispiro-oxindolylpyrrolothiazoles and their antimycobacterial evaluation.
2010 Dec 15
A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents.
2010 Jan 1
Murine models of premature ageing for the study of diet-induced immune changes: improvement of leucocyte functions in two strains of old prematurely ageing mice by dietary supplementation with sulphur-containing antioxidants.
2010 Nov
Patents

Patents

WO1995031194A1
2

Sample Use Guides

In Vitro Use Guide
Unknown
Name Type Language
TIMONACIC
INCI   INN   MART.   MI   WHO-DD  
INCI   INN  
Official Name English
NSC-25855
Code English
timonacic [INN]
Common Name English
NORGAMEN
Common Name English
THIOPROLINE
Systematic Name English
HEPACOM
Brand Name English
TIMONACIC [MART.]
Common Name English
ATC
Common Name English
TIMONACIC [MI]
Common Name English
4-THIAZOLIDINECARBOXYLIC ACID
Systematic Name English
Timonacic [WHO-DD]
Common Name English
TIMONACIC [INCI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2132
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C2354
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
MESH
C003438
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
PUBCHEM
9934
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID9023675
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
FDA UNII
E5913T3IBL
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
INN
3782
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
EVMPD
SUB11070MIG
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
MERCK INDEX
m10872
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY Merck Index
SMS_ID
100000077224
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-146-6
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
NSC
25855
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
CAS
2756-91-4
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
SUPERSEDED
DRUG CENTRAL
2670
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL358722
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
DRUG BANK
DB12856
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
CAS
444-27-9
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
CHEBI
64564
Created by admin on Fri Dec 15 15:15:34 GMT 2023 , Edited by admin on Fri Dec 15 15:15:34 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of TIMONACIC
SALT/SOLVATE (PARENT)
Structure of TIMONACIC ARGININE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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