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Details

Stereochemistry EPIMERIC
Molecular Formula C6H14N4O2.C4H7NO2S
Molecular Weight 307.37
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIMONACIC ARGININE

SMILES

OC(=O)C1CSCN1.N[C@@H](CCCNC(N)=N)C(O)=O

InChI

InChIKey=JEOQACOXAOEPLX-WCCKRBBISA-N
InChI=1S/C6H14N4O2.C4H7NO2S/c7-4(5(11)12)2-1-3-10-6(8)9;6-4(7)3-1-8-2-5-3/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);3,5H,1-2H2,(H,6,7)/t4-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C6H14N4O2
Molecular Weight 174.201
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H7NO2S
Molecular Weight 133.169
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

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

Originator

Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/timonacic.html

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Heparegen

Approved Use

Heparegen (Timonacic) is used as a hepatoprotective agent
Primary
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
Novel dipeptide macrocycles from 4-oxo, -thio, and -amino-substituted proline derivatives.
2002 May 31
Improvement of the macrophage functions in prematurely ageing mice by a diet supplemented with thiolic antioxidants.
2004
Formaldehyde scavenging from peritoneal dialysis solutions using reduced aminothiol compounds.
2004 Apr
A one-pot total synthesis of crambin.
2004 May 3
Synthesis, calpain inhibitory activity, and cytotoxicity of P2-substituted proline and thiaproline peptidyl aldehydes and peptidyl alpha-ketoamides.
2006 Aug 24
Successful computer guided planned synthesis of (4R)-thiazolidine carboxylic acid and its 2-substituted analogues as urease inhibitors.
2006 May
Conformational studies of proline-, thiaproline- and dimethylsilaproline-containing diketopiperazines.
2006 Oct
Ingestion of thioproline suppresses rat esophageal adenocarcinogenesis caused by duodenogastroesophageal reflux.
2007 Dec
Identification of gene markers for formaldehyde exposure in humans.
2007 Oct
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
Actions of a proline analogue, L-thiazolidine-4-carboxylic acid (T4C), on Trypanosoma cruzi.
2009
Purification, characterization and crystallization of pyrroline-5-carboxylate reductase from the hyperthermophilic archeon Sulfolobus Solfataricus.
2009 Apr
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
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

Substance Class Chemical
Created
by admin
on Sat Dec 16 11:22:09 GMT 2023
Edited
by admin
on Sat Dec 16 11:22:09 GMT 2023
Record UNII
UIB16M6D10
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIMONACIC ARGININE
WHO-DD  
Common Name English
Timonacic arginine [WHO-DD]
Common Name English
ARGININE THIAZOLIDINECARBOXYLATE
Common Name English
L-ARGININE, 4-THIAZOLIDINECARBOXYLATE (1:1)
Systematic Name English
L-ARGININE, MONO-4-THIAZOLIDINECARBOXYLATE
Systematic Name English
SULFILE
Brand Name English
4-THIAZOLIDINECARBOXYLIC ACID, COMPD. WITH L-ARGININE (1:1)
Systematic Name English
ARGININE 4-THIAZOLIDINECARBOXYLATE
Systematic Name English
4-THIAZOLIDINECARBOXYLIC ACID SALT WITH ARGININE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
UIB16M6D10
Created by admin on Sat Dec 16 11:22:09 GMT 2023 , Edited by admin on Sat Dec 16 11:22:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
260-857-3
Created by admin on Sat Dec 16 11:22:09 GMT 2023 , Edited by admin on Sat Dec 16 11:22:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID00973205
Created by admin on Sat Dec 16 11:22:09 GMT 2023 , Edited by admin on Sat Dec 16 11:22:09 GMT 2023
PRIMARY
PUBCHEM
9883032
Created by admin on Sat Dec 16 11:22:09 GMT 2023 , Edited by admin on Sat Dec 16 11:22:09 GMT 2023
PRIMARY
CAS
57631-15-9
Created by admin on Sat Dec 16 11:22:09 GMT 2023 , Edited by admin on Sat Dec 16 11:22:09 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY