OXOTHIAZOLIDINECARBOXYLIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C4H5NO3S
Molecular Weight	147.152
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of OXOTHIAZOLIDINECARBOXYLIC ACID

Structure Search

SMILES

OC(=O)[C@@H]1CSC(=O)N1

InChI

InChIKey=BMLMGCPTLHPWPY-REOHCLBHSA-N

InChI=1S/C4H5NO3S/c6-3(7)2-1-9-4(8)5-2/h2H,1H2,(H,5,8)(H,6,7)/t2-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9604807

Oxothiazolidinecarboxylic Acid (L-2-oxothiazolidine-4-carboxylic acid, OTC) was currently undergoing evaluation in a Phase II clinical trial. It is suggested that an ideal drug may be an antisense oligonucleotide that blocks the expression of glycolate oxidase, a key enzyme in hepatic oxalate synthesis.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 67 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9144376	Inhibitor 8297
Glutathione synthetase 7 Target ID: P48637 Gene ID: 2937.0 Gene Symbol: GSS Target Organism: Homo sapiens (Human) Sources: http://adisinsight.springer.com/drugs/800002203	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
HIV-1 infection 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9590463 http://adisinsight.springer.com/drugs/800002203	Primary	Phase II 1132	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: http://adisinsight.springer.com/drugs/800002203 https://www.ncbi.nlm.nih.gov/pubmed/9502783	Primary	Phase I 428	Unknown Approved Use Unknown
Amyotrophic lateral sclerosis 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10227642 http://adisinsight.springer.com/drugs/800002203	Primary	Phase I 428	Unknown Approved Use Unknown
Adult respiratory distress syndrome 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18209670 http://adisinsight.springer.com/drugs/800002203	Primary	Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
734 nmol/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590463	4500 mg single, oral dose: 4500 mg route of administration: Oral experiment type: SINGLE co-administered:	OXOTHIAZOLIDINECARBOXYLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
242 nmol/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590463	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	OXOTHIAZOLIDINECARBOXYLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
105 nmol/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590463	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	OXOTHIAZOLIDINECARBOXYLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
4063 nmol × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590463	4500 mg single, oral dose: 4500 mg route of administration: Oral experiment type: SINGLE co-administered:	OXOTHIAZOLIDINECARBOXYLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
428 nmol × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590463	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered:	OXOTHIAZOLIDINECARBOXYLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED
88 nmol × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590463	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	OXOTHIAZOLIDINECARBOXYLIC ACID plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse events
100 mg/kg 1 times / 8 hours multiple, intravenous Highest studied dose Dose: 100 mg/kg, 1 times / 8 hours Route: intravenous Route: multiple Dose: 100 mg/kg, 1 times / 8 hours Sources: https://pubmed.ncbi.nlm.nih.gov/9186317 Page: p.35	healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/9186317 Page: p.35	Sources: https://pubmed.ncbi.nlm.nih.gov/9186317 Page: p.35
0.5 g 3 times / day multiple, oral Studied dose Dose: 0.5 g, 3 times / day Route: oral Route: multiple Dose: 0.5 g, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9621294 Page: p.1097	unhealthy, ADULT n = 10 Health Status: unhealthy Condition: renal failure - chronic Age Group: ADULT Sex: M+F Food Status: FED Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/9621294 Page: p.1097	Sources: https://pubmed.ncbi.nlm.nih.gov/9621294 Page: p.1097

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY438059	https://www.001chemical.com/chem/search?q=DY438059
1PlusChem LLC	1P002BAT	https://www.1pchem.com/search?query=1P002BAT
1PlusChem LLC	1P002BG2	https://www.1pchem.com/search?query=1P002BG2
A2B Chem	AB07157	http://a2bchem.com/prod/AB07157
A2B Chem	AB07346	http://a2bchem.com/prod/AB07346
AA Blocks	AA002ARD	http://aablocks.com/goods/Goods/detail?id=AA002ARD
AA Blocks	AA002AWM	http://aablocks.com/goods/Goods/detail?id=AA002AWM
AK Scientific	7290AH	https://aksci.com/item_detail.php?cat=7290AH
Ambeed	A144428	http://www.ambeed.com/search/Search.html?keyword=A144428
Angene	AGN-PC-0O6QYF	http://www.angenechemical.com/productshow/AGN-PC-0O6QYF.html
BOC Sciences	19771-63-2	http://www.bocsci.com/description.asp?cas=19771-63-2
BOC Sciences	77273-78-0	http://www.bocsci.com/description.asp?cas=77273-78-0
Bachem	Q-1535	https://shop.bachem.com/catalogsearch/result/?q=Q-1535
BioSynth	J-501467	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501467
Chem Scene	CS-0110970	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0110970
Chem-Impex International	6280	http://www.chemimpex.com/category/search/06280/2?filter=&search=06280&type=q&keywordoption=ANY&cid=2&fltrdesc=
Combi-Blocks	QB-7063	http://www.combi-blocks.com/cgi-bin/find.cgi?QB-7063
Creative Peptides	CP26611	https://www.creative-peptides.com/search?q=CP26611
Enamine	BBV-38393605	http://www.enaminestore.com/catalog/BBV-38393605
Enamine	BBV-38716335	http://www.enaminestore.com/catalog/BBV-38716335
Enamine	EN300-24554	https://www.enaminestore.com/catalog/EN300-24554
Enamine	EN300-34862	https://www.enaminestore.com/catalog/EN300-34862
Fluorochem	358305	http://www.fluorochem.co.uk/Products/Product?code=358305
Hairui	HR131860	http://www.hairuichem.com/en/product/search.do?q=HR131860
KeyOrganics	DS-11903	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-11903
Lab Network	LN01364255	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01364255
MedChem Express	HY-133105	https://www.medchemexpress.com/search.html?q=HY-133105&ft=&fa=&fp=
MolPort	MolPort-002-471-287	https://www.molport.com/shop/molecule-link/MolPort-002-471-287
MolPort	MolPort-003-356-154	https://www.molport.com/shop/molecule-link/MolPort-003-356-154
Molcore	MC438059	http://www.molcore.com/CatMC438059.html
MuseChem	M000519	https://www.musechem.com/product/M000519.html
PI Chemicals	PI-47157	http://www.pipharm.com/catalog_products/PI-47157.html
TargetMol	T5365	https://www.targetmol.com/search?keyword=T5365
Tetrahedron	TS07313	http://www.thsci.com/search.do?q=TS07313
TimTec	SBB004097	http://www.echemstore.com/catalogsearch/result/?q=SBB004097
TimTec	ST075445	http://www.echemstore.com/catalogsearch/result/?q=ST075445
Toronto Research Chemicals	B291430	https://www.trc-canada.com/product-detail/?CatNum=B291430
Toronto Research Chemicals	O870505	https://www.trc-canada.com/product-detail/?CatNum=O870505
eMolecules	299987829	https://orderbb.emolecules.com/search/#?query=299987829
eMolecules	3801413	https://orderbb.emolecules.com/search/#?query=3801413
eMolecules	496157	https://orderbb.emolecules.com/search/#?query=496157
eNovation Chemicals	D746593	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D746593&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-4574359237	https://mcule.com/MCULE-4574359237/
mcule	MCULE-9439896780	https://mcule.com/MCULE-9439896780/

PubMed

Title	Date	PubMed
L-2-oxothiazolidine-4-carboxylic acid, a cysteine prodrug: pharmacokinetics and effects on thiols in plasma and lymphocytes in human.	1991 Apr	2019996
The pharmacokinetics and pharmaco-dynamics of Procysteine in amyotrophic lateral sclerosis.	1999 Apr 22	10227642
Dietary antioxidants prevent alcohol-induced ciliary dysfunction.	2013 Dec	24169090

Patents

Sample Use Guides

In Vivo Use Guide

Oxothiazolidinecarboxylic Acid (L-2-oxothiazolidine-4-carboxylic acid, OTC), a prodrug of cysteine, was administered at a dose of 0.15 and 0.45 mmol/kg to healthy volunteers. The plasma concentration of OTC reached a peak between 45 and 60 min after p.o. administration.

Route of Administration: Oral

In Vitro Use Guide

Oxothiazolidinecarboxylic Acid (L-2-oxothiazolidine-4-carboxylic acid, OTC) was tested at concentrations of 5, 10, and 20 mM for its effect on acute and chronic HIV-1 infection as measured by RT activity in MDM isolated from adult peripheral blood and cord blood. Addition of OTC at a concentration of 10 or 20 mM to chronically infected cord blood MDM cultures also suppressed RT activity during the subsequent course of infection.

Name

Type

Language

OXOTHIAZOLIDINECARBOXYLIC ACID

Official Name

English

(R)-2-OXOTHIAZOLIDINE-4-CARBOXYLIC ACID

Systematic Name

English

2-OXO-L-THIAZOLIDINE-4-CARBOXYLIC ACID

Common Name

English

4-THIAZOLIDINECARBOXYLIC ACID, 2-OXO-, (R)-

Common Name

English

(-)-2-OXO-4-THIAZOLIDINECARBOXYLIC ACID

Systematic Name

English

L-2-OXO-4-THIAZOLIDINECARBOXYLIC ACID [MI]

Common Name

English

(R)-(-)-2-OXOTHIAZOLIDINE-4-CARBOXYLIC ACID

Systematic Name

English

L-2-OXOTHIAZOLIDINE-4-CARBOXYLIC ACID

Brand Name

English

(4R)-2-OXO-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID

Systematic Name

English

OXOTHIAZOLIDINECARBOXYLIC ACID [INCI]

Common Name

English

2-OXO-4-THIAZOLIDINECARBOXYLIC ACID, L-

Common Name

English

KOPROSTEINE

Brand Name

English

(4R)-2-OXOTHIAZOLIDINE-4-CARBOXYLIC ACID

Systematic Name

English

PROCYSTEINE

Common Name

English

L-2-OXO-4-THIAZOLIDINECARBOXYLIC ACID

Common Name

English

R-2-OXO-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID

Common Name

English

4-THIAZOLIDINECARBOXYLIC ACID, 2-OXO-, (4R)-

Common Name

English

4-THIAZOLIDINECARBOXYLIC ACID, 2-OXO-, L-

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

99296