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

Molecular Formula	C4H5NO3S
Molecular Weight	147.152
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:52:42 GMT 2023` Edited by `admin` on `Sat Dec 16 01:52:42 GMT 2023`
Record UNII	X7063P804E
Record Status	`Validated (UNII)`
Record Version

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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