Timonacic

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 Search

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
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01280a050 | https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=39714 | https://www.drugs.com/international/timonacic.html | https://www.ncbi.nlm.nih.gov/pubmed/6764606

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

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Liver diseases 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14134266 https://www.ncbi.nlm.nih.gov/pubmed/14308584	Primary		Approved 8583	Heparegen Approved Use Heparegen (Timonacic) is used as a hepatoprotective agent
Liver diseases 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14134266 https://www.ncbi.nlm.nih.gov/pubmed/14308584	Primary		Approved 8583	Arbitol Approved Use Arbitol (Timonacic) is used as a hepatoprotective agent

PubMed

Title	Date	PubMed
A facile 1,3-dipolar cycloaddition of azomethine ylides to 2-arylidene-1,3-indanediones: synthesis of dispiro-oxindolylpyrrolothiazoles and their antimycobacterial evaluation.	2010-12-15	21071220
A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation.	2010-12	20932607
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.	2010-11	20875196
A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents.	2010-01-01	19900810
Synthesis, structure and structure-activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents.	2009-10	19423200
An atom economic synthesis and antitubercular evaluation of novel spiro-cyclohexanones.	2009-07-01	19473840
Purification, characterization and crystallization of pyrroline-5-carboxylate reductase from the hyperthermophilic archeon Sulfolobus Solfataricus.	2009-04	19027071
Actions of a proline analogue, L-thiazolidine-4-carboxylic acid (T4C), on Trypanosoma cruzi.	2009	19229347
Lithium thiazolidine-4-carboxylate: synthesis, spectroscopic characterization and preliminary in vitro cytotoxic studies in human HeLa cells.	2008-12-01	18353709
Detection of endogenous DNA adducts, O-carboxymethyl-2'-deoxyguanosine and 3-ethanesulfonic acid-2'-deoxycytidine, in the rat stomach after duodenal reflux.	2008-09	18549406
Investigation toward multi-epitope vaccine candidates using native chemical ligation.	2008	18979543
Ingestion of thioproline suppresses rat esophageal adenocarcinogenesis caused by duodenogastroesophageal reflux.	2007-12	17982628
An expanded set of amino acid analogs for the ribosomal translation of unnatural peptides.	2007-10-03	17912351
Identification of gene markers for formaldehyde exposure in humans.	2007-10	17938736
Determination of thiazolidine-4-carboxylates in urine by chloroformate derivatization and gas chromatography-electron impact mass spectrometry.	2007-09	17610311
Liver fluke induces cholangiocarcinoma.	2007-07	17622191
Dietary thioproline decreases spontaneous food intake and increases survival and neurological function in mice.	2007-01	17115892
Conformational studies of proline-, thiaproline- and dimethylsilaproline-containing diketopiperazines.	2006-10	16786506
Synthesis, calpain inhibitory activity, and cytotoxicity of P2-substituted proline and thiaproline peptidyl aldehydes and peptidyl alpha-ketoamides.	2006-08-24	16913717
Thioproline prevents carcinogenesis in the remnant stomach induced by duodenal reflux.	2006-06-18	16051425
Successful computer guided planned synthesis of (4R)-thiazolidine carboxylic acid and its 2-substituted analogues as urease inhibitors.	2006-05	16710811
Impact of cis-proline analogs on peptide conformation.	2006-04-05	16358327
A one-pot total synthesis of crambin.	2004-05-03	15127445
Thioproline inhibits development of esophageal adenocarcinoma induced by gastroduodenal reflux in rats.	2004-05	14754873
Formaldehyde scavenging from peritoneal dialysis solutions using reduced aminothiol compounds.	2004-04	15056264
Bombesin antagonists inhibit proangiogenic factors in human experimental breast cancers.	2004-01-12	14710236
Improvement of the macrophage functions in prematurely ageing mice by a diet supplemented with thiolic antioxidants.	2004	15607048
Expression of Sonic hedgehog-Fc fusion protein in Pichia pastoris. Identification and control of post-translational, chemical, and proteolytic modifications.	2003-06	12767820
New water-soluble prodrugs of HIV protease inhibitors based on O-->N intramolecular acyl migration.	2002-12	12413869
A diet supplemented with thiolic anti-oxidants improves leucocyte function in two strains of prematurely ageing mice.	2002-11	12366393
Novel dipeptide macrocycles from 4-oxo, -thio, and -amino-substituted proline derivatives.	2002-05-31	12027716
The amount of thiolic antioxidant ingestion needed to improve several immune functions is higher in aged than in adult mice.	2002-02	11999379
Retinoic acid exacerbates experimental radiation nephropathy.	2002-02	11835684
Oxidation of L-thiazolidine-4-carboxylate by delta1-pyrroline-5-carboxylate reductase in Escherichia coli.	2001-06	11381339
Enhanced potency of human Sonic hedgehog by hydrophobic modification.	2001-04-10	11284692
Screening for new compounds with antiherpes activity.	1984-10	6517562

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

HEPACOM

Preferred Name

English

Timonacic

Official Name

English

NSC-25855

Code

English

timonacic [INN]

Common Name

English

NORGAMEN

Common Name

English

THIOPROLINE

Systematic 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

Classification Tree Code System Code

NCI_THESAURUS

C2132