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

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	( + / - )

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 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14134266 https://www.ncbi.nlm.nih.gov/pubmed/14308584	Primary		Approved 8429	Heparegen Approved Use Heparegen (Timonacic) is used as a hepatoprotective agent
Liver diseases 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14134266 https://www.ncbi.nlm.nih.gov/pubmed/14308584	Primary		Approved 8429	Arbitol Approved Use Arbitol (Timonacic) is used as a hepatoprotective agent

PubMed

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

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:15:34 GMT 2023` Edited by `admin` on `Fri Dec 15 15:15:34 GMT 2023`
Record UNII	E5913T3IBL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIMONACIC

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