Page last updated: 2024-12-06

2-oxothiazolidine-4-carboxylic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-oxothiazolidine-4-carboxylic acid: analog of 5-oxoproline in which the 4-methylene moiety is replaced by sulfur; acts as 5-oxo-L-prolinase substrate; structure in first source; RN given refers to parent cpd without isomeric designation; Procysteine is a trade name [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65272
SCHEMBL ID83023
MeSH IDM0094190

Synonyms (26)

Synonym
LS-12981
HMS3393K09
nsc342431
nsc-342431
OPREA1_698154
l-2-oxothiazolidine-4-carboxylic acid
2-oxothiazolidine-4-carboxylic acid
4-thiazolidinecarboxylic acid, 2-oxo-
2-oxo-1,3-thiazolidine-4-carboxylic acid
FT-0693449
19750-45-9
2-oxo-4-thiazolidinecarboxylic acid
(-)-2-oxo-4-thiazolidinecarboxylic acid
FT-0627585
SCHEMBL83023
2-oxothiazolidin-4-carboxylic acid
BMLMGCPTLHPWPY-UHFFFAOYSA-N
AKOS024015355
l -2-oxothiazolidine-4-carboxylic acid
otc;procysteine;otz;l-thiazolidin-2-one-4-carboxylic acid
4-thiazolidinecarboxylicacid,2-oxo-(7ci,8ci,9ci)
AT20226
DTXSID00864902
EN300-34862
2-oxothiazolidine-4-carboxylicacid
Z199409846

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Administration of a toxic dose of precocene II (175 mg/kg) to male Sprague-Dawley rats rapidly depleted hepatic GSH, produced histopathological changes in the liver, and induced increases in serum aminotransferase activity."( Alteration of precocene II-induced hepatotoxicity by modulation of hepatic glutathione levels.
Duddy, SK; Hsia, MT, 1989
)
0.28
"Hymenoxon and helenalin are toxic sesquiterpene lactones present in the toxic range plants Hymenoxys odorata and Helenium microcephalum."( Role of glutathione in the toxicity of the sesquiterpene lactones hymenoxon and helenalin.
Hayes, MA; Kim, HL; Merrill, JC; Murray, CA; Safe, S, 1988
)
0.27
" In this investigation, we have found that sensitivity to CHCl3 correlates with the capacity of the kidney to metabolize CHCl3 to the toxic metabolite phosgene (COCl2)."( Strain and sex differences in chloroform-induced nephrotoxicity. Different rates of metabolism of chloroform to phosgene by the mouse kidney.
George, JW; Pohl, LR; Satoh, H,
)
0.13
" Pretreatment with phenobarbital enhanced the toxic response of renal cortical slices to CHCl3 in vitro as indicated by decreased p-aminohippurate and tetraethylammonium accumulation."( Mechanism of chloroform nephrotoxicity. IV. Phenobarbital potentiation of in vitro chloroform metabolism and toxicity in rabbit kidneys.
Bailie, MB; Hook, JB; Newton, JF; Smith, JH, 1984
)
0.27
" Two groups could be distinguished: PMA, EMT and MMC are one order of magnitude more toxic than MC, MN and MA."( Cytotoxicity of mercury compounds in LLC-PK1, MDCK and human proximal tubular cells.
Bohets, HH; D'Haese, PC; De Broe, ME; Dierickx, PJ; Nouwen, EJ; Van der Biest, I; Van Landeghem, GF; Van Thielen, MN, 1995
)
0.29
" Spermine proved highly toxic and growth rates were reduced compared with controls when even ."( Toxicity and growth-promoting potential of spermine when fed to chicks.
Smith, TK; Sousadias, MG, 1995
)
0.29
"Amino acids (AA) which were proposed as an alternative osmotically active agents in dialysates are toxic to human peritoneal mesothelial cells (HPMC) due to disturbance of the antioxidant-oxidant balance in cells by reducing level of glutathione."( In vitro effect of glutathione precursors on cytotoxicity of amino acids to human mesothelial cells.
Grzybowski, AE, 1999
)
0.3
" Because OTZ reduced the toxic effects of GDP on mesothelial cells, this compound may improve biocompatibility of peritoneal dialysis fluids."( L-2-oxothiazolidine-4-carboxylic acid reduces in vitro cytotoxicity of glucose degradation products.
Breborowicz, A; Oreopoulos, D; Polubinska, A; Pyda, M; Witowski, J, 2004
)
1.04
" Cytotoxicity and cell proliferation assays were performed to elucidate the adverse effects of formaldehyde on U2OS cells."( Cytotoxicity of formaldehyde on human osteoblastic cells is related to intracellular glutathione levels.
Chang, YC; Ho, YC; Huang, FM, 2007
)
0.34
"Cytotoxicity, cell proliferation and collagen synthesis assays were performed to elucidate the toxic effects of CHX on the human osteoblastic cell line U2OS."( Cytotoxicity of chlorhexidine on human osteoblastic cells is related to intracellular glutathione levels.
Chang, YC; Chou, MY; Hu, CC; Lee, SS; Lee, TH, 2010
)
0.36

Pharmacokinetics

ExcerptReferenceRelevance
"In 13 subjects with ALS, we studied the safety and pharmacokinetic properties of Procysteine, a cysteine prodrug that increases levels of intracellular glutathione."( The pharmacokinetics and pharmaco-dynamics of Procysteine in amyotrophic lateral sclerosis.
Brown, RH; Cudkowicz, ME; Ellis, T; Gwilt, PR; Hayden, DL; Sexton, PM; Whalen, J, 1999
)
0.3

Bioavailability

ExcerptReferenceRelevance
" Diminished antioxidant capacity increases vascular superoxide levels, which reduce NO bioavailability and promote peroxynitrite generation."( Vascular oxidative stress and nitric oxide depletion in HIV-1 transgenic rats are reversed by glutathione restoration.
Dikalov, S; Guidot, DM; Hart, CM; Jones, DP; Kleinhenz, DJ; Kline, ER; Liang, B; Sutliff, RL, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" with 950 mg/kg of OTC 4 hours before dosing with 5-FU."( Effects of L-2-oxothiazolidine-4-carboxylate, a cysteine pro-drug, on teratogenicity of 5-fluorouracil in mice.
Deguchi, T; Mataki, Y; Naya, M; Noguchi, M; Yasuda, M, 1990
)
0.28
" N-Acetyl-L-cysteine, L-2-oxothiazolidine-4-carboxylate or the L- or D-isomers of 2-methylthiazolidine-4-carboxylate were administered to male mice immediately after a hepatotoxic dosage of acetaminophen (5."( Effects of cysteine pro-drugs on acetaminophen-induced hepatotoxicity.
Hazelton, GA; Hjelle, JJ; Klaassen, CD, 1986
)
0.27
" Increases in whole-blood glutathione were observed in the highest dosage group after 6 weeks of therapy."( A phase I/II trial of intravenous L-2-oxothiazolidine-4-carboxylic acid (procysteine) in asymptomatic HIV-infected subjects.
Borum, PR; Chance, M; Emgushov, RT; Jackson, JB; Kalayjian, RC; Mayer, KH; Skowron, G; Spell, SA; Webb, LS; Yen-Lieberman, B, 1994
)
0.56
" In one study, acute high dosage survivorship was compared for approximately equimolar cysteine dosages of L-cysteine and Procysteine."( Toxicity evaluations of L-cysteine and Procysteine, a cysteine prodrug, given once intravenously to neonatal rats.
Glosson, JA; Goldberg, DI; Madsen, DC; Rowe, WB; White, RD; Wilson, DM, 1993
)
0.29
" Further studies are needed to investigate optimal dosage scheme, mechanism of action, and interference with anti-tumor activity and prevention of long-term side effects of cyclophosphamide."( Protective effects of L-2-oxothiazolidine-4-carboxylate treatment on cyclophosphamide-induced cystitis in rats.
Gordon, D; Leaf, C; Rice, D; Safron, J; White, R, 1997
)
0.3
"A randomized double-blind, placebo-controlled study was conducted in 37 asymptomatic HIV-infected individuals (mean CD4 count 707 cells/mm3) to characterize the safety, pharmacokinetics, and effect on blood thiols of three dosage levels of a cysteine prodrug, L-2-oxothiazolidine-4-carboxylic acid (OTC; Procysteine; Clintec Technologies, Deerfield, IL)."( A phase I/II evaluation of oral L-2-oxothiazolidine-4-carboxylic acid in asymptomatic patients infected with human immunodeficiency virus.
Barditch-Crovo, P; Borum, P; Buier, R; Goldberg, D; Kalayjian, RC; Lederman, M; Lietman, P; Noe, D; Rowe, WB; Skowron, G, 1998
)
0.76
" Procysteine enters CSF after both IV and oral dosing and accumulates to significant levels in CSF."( The pharmacokinetics and pharmaco-dynamics of Procysteine in amyotrophic lateral sclerosis.
Brown, RH; Cudkowicz, ME; Ellis, T; Gwilt, PR; Hayden, DL; Sexton, PM; Whalen, J, 1999
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (221)

TimeframeStudies, This Drug (%)All Drugs %
pre-199044 (19.91)18.7374
1990's89 (40.27)18.2507
2000's58 (26.24)29.6817
2010's28 (12.67)24.3611
2020's2 (0.90)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index21.37 (24.57)
Research Supply Index5.51 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index17.79 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (4.22%)5.53%
Reviews8 (3.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other219 (92.41%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]