Page last updated: 2024-09-29

thiobarbituric acid

Description

thiobarbituric acid: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-thiobarbituric acid : A barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID2723628
CHEBI ID33202
SCHEMBL ID16027
SCHEMBL ID22275895
SCHEMBL ID24459312
MeSH IDM0094530

Synonyms (69)

Synonym
4,5h)-pyrimidinedione, 2-mercapto-
nsc-4733
2-thiobarbituric acid
barbituric acid, 2-thio-
usaf ek-660
wln: t6vmymv fhj cus
504-17-6
thiobarbituric acid
4,6-dihydroxy-2-thiopyrimidine
thiobarbiturate
wln: t6mv dvn chj fsh
nsc4733
2-thio-4,6-dioxypyrimidine
2-mercapto-4,6-dihydroxypyrimidine
4,5h)-pyrimidinedione, dihydro-2-thioxo-
bathyran
einecs 207-985-8
4,6(1h,5h)-pyrimidinedione, 2-mercapto-
nsc 4733
2-mercaptobarbituric acid
austranal
barbituric acid, 2-thio- (van)
ai3-60340
2-mercapto-4,6-dihydroxypyrimidine (van)
4,6(1h,5h)-pyrimidinedione, dihydro-2-thioxo-
2-thioxodihydropyrimidine-4,6(1h,5h)-dione
2-sulfanylidenedihydropyrimidine-4,6(1h,5h)-dione
CHEBI:33202 ,
dihydro-2-thioxo-4,6(1h,5h)-pyrimidinedione
STK364864
2-thiobarbituric acid, >=98%
2-thioxohexahydropyrimidine-4,6-dione
inchi=1/c4h4n2o2s/c7-2-1-3(8)6-4(9)5-2/h1h2,(h2,5,6,7,8,9)
rvbuggbmjdpost-uhfffaoysa-
AKOS000118917
thiobarbituric
2-sulfanylidene-1,3-diazinane-4,6-dione
A828112
AKOS005208867
STL281357
2-sulfanylpyrimidine-4,6(1h,5h)-dione
unii-m1yzw5ss7c
nsc 266155
m1yzw5ss7c ,
FT-0617250
EPITOPE ID:120357
2-thioxo-dihydropyrimidine-4,6(1h,5h)-dione
SCHEMBL16027
2-thiopyrimidine-4,6-diol
1,2,3,4,5,6-hexahydro-4,6-dioxopyrimidine-2-thione
hexahydropyrimidine-4,6-dione-2-thione
DTXSID7060124
2-thioxodihydro-4,6(1h,5h)-pyrimidinedione #
W-105964
BS-3816
F8881-1568
2-thiobarbituric acid, purum, >=98.0% (s)
mfcd00006674
2-mercapto-pyrimidine-4,6-dione
EN300-19231
2-thiobarbituric acid, vetec(tm) reagent grade, >=98%
Q418230
(1-naphthylacetyl)amino]aceticacid
AMY291
SCHEMBL22275895
nsc4733nsc 4733
SCHEMBL24459312
nsc4733, nsc-4733, nsc 4733
Z104473236

Effects

ExcerptReference
"Thiobarbituric acid (TBA) has been considered a privileged structure for developing antimicrobial agents. "( Albericio, F; Almarhoon, ZM; de la Torre, BG; El-Faham, A; Hazzah, HA; Noki, S; Sharma, A; Zamisa, SJ, 2018)

Treatment

ExcerptReference
"The thiobarbituric acid value of treatment B was significantly higher than that of the control and treatment A."( Ahn, J; Jung, TH; Kim, JJ; Kwak, HS, 2006)

Roles (2)

RoleDescription
reagentA substance used in a chemical reaction to detect, measure, examine, or produce other substances.
allergenA chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
barbituratesMembers of the class of pyrimidones consisting of pyrimidine-2,4,6(1H,3H,5H)-trione (barbituric acid) and its derivatives. Largest group of the synthetic sedative/hypnotics, sharing a characteristic six-membered ring structure.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyphenol oxidase 2Agaricus bisporusIC50 (µMol)200.00000.03403.987110.0000AID436860
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Taste receptor type 2 member 38Homo sapiens (human)Activity10,000.00000.15003.256310.0000AID1619469
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
detection of chemical stimulus involved in sensory perception of bitter tasteTaste receptor type 2 member 38Homo sapiens (human)
G protein-coupled receptor signaling pathwayTaste receptor type 2 member 38Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
G protein-coupled receptor activityTaste receptor type 2 member 38Homo sapiens (human)
bitter taste receptor activityTaste receptor type 2 member 38Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
plasma membraneTaste receptor type 2 member 38Homo sapiens (human)
membraneTaste receptor type 2 member 38Homo sapiens (human)
membraneTaste receptor type 2 member 38Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID436860Inhibition of mushroom tyrosinase2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities.
AID436861Inhibition of mushroom tyrosinase at 200 uM2009European journal of medicinal chemistry, Oct, Volume: 44, Issue:10
Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities.
AID1154175Inhibition of mushroom tyrosinase diphenolase activity using L-DOPA as substrate assessed as formation of DOPAchrome at 100 uM preincubated for 10 mins followed by substrate addition measured for 1 min relative to control2014Bioorganic & medicinal chemistry, Jul-01, Volume: 22, Issue:13
Design, synthesis and biological evaluation of hydroxy- or methoxy-substituted 5-benzylidene(thio) barbiturates as novel tyrosinase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (985)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990322 (32.69)18.7374
1990's348 (35.33)18.2507
2000's129 (13.10)29.6817
2010's161 (16.35)24.3611
2020's25 (2.54)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials13 (1.24%)5.53%
Reviews10 (0.96%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other1,022 (97.80%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (24)

ArticleYear
Acute toxicity and effects of Roundup Original® on pintado da Amazônia.
Environmental science and pollution research international, Volume: 25, Issue: 25
2018
Chronic mild stress augments MPTP induced neurotoxicity in a murine model of Parkinson's disease.
Physiology & behavior, 05-01, Volume: 173
2017
EPR detection of paramagnetic chromium in liver of fish (Anguilla anguilla) treated with dichromate(VI) and associated oxidative stress responses-contribution to elucidation of toxicity mechanisms.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, Volume: 157, Issue: 2
2013
Pyruvate attenuates cardiac dysfunction and oxidative stress in isoproterenol-induced cardiotoxicity.
Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie, Volume: 64, Issue: 4
2012
Protective effects of an extract of young radish (Raphanus sativus L) cultivated with sulfur (sulfur-radish extract) and of sulforaphane on carbon tetrachloride-induced hepatotoxicity.
Bioscience, biotechnology, and biochemistry, Volume: 72, Issue: 5
2008
N-acetyl-l-cysteine affords protection against lead-induced cytotoxicity and oxidative stress in human liver carcinoma (HepG2) cells.
International journal of environmental research and public health, Volume: 4, Issue: 2
2007
Determination of total antioxidant activity in three types of local vegetables shoots and the cytotoxic effect of their ethanolic extracts against different cancer cell lines.
Asia Pacific journal of clinical nutrition, Volume: 13, Issue: 3
2004
Synergistic protection of PC12 cells from beta-amyloid toxicity by resveratrol and catechin.
Brain research bulletin, Nov-15, Volume: 62, Issue: 1
2003
Determination of total antioxidant activity in three types of local vegetables shoots and the cytotoxic effect of their ethanolic extracts against different cancer cell lines.
Asia Pacific journal of clinical nutrition, Volume: 12, Issue: 3
2003
Effect of metal removal on the toxicity of airborne particulate matter from the Utah Valley.
Inhalation toxicology, Volume: 14, Issue: 10
2002
An assessment of docosahexaenoic acid intake from the viewpoint of safety and physiological efficacy in matured rats.
Annals of nutrition & metabolism, Volume: 46, Issue: 5
2002
Methamphetamine-induced striatal dopamine neurotoxicity and cyclooxygenase-2 protein expression in BALB/c mice.
Neuropharmacology, Jan-28, Volume: 39, Issue: 3
2000
Articular chondrocytes and synoviocytes in a co-culture system: influence on reactive oxygen species-induced cytotoxicity and lipid peroxidation.
Cell and tissue research, Volume: 296, Issue: 3
1999
Methanol potentiation of carbon tetrachloride hepatotoxicity: the central role of cytochrome P450.
Toxicology, Aug-16, Volume: 112, Issue: 2
1996
Protective effect of levamisole on carbon tetrachloride-induced lipid peroxidation and hepatotoxicity.
Biomedicine / [publiee pour l'A.A.I.C.I.G.], Volume: 35, Issue: 7-8
1981
Protection by BCG, levamisole, PS-K, OK-432, and vitamin E against carbon tetrachloride hepatotoxicity.
Hepato-gastroenterology, Volume: 29, Issue: 6
1982
Sex differences in ferric nitrilotriacetate-induced lipid peroxidation and nephrotoxicity in mice.
Biochimica et biophysica acta, Nov-04, Volume: 963, Issue: 1
1988
Metabolism of SR 4233 by Chinese hamster ovary cells: basis of selective hypoxic cytotoxicity.
Cancer research, Nov-01, Volume: 48, Issue: 21
1988
Induction of lipid peroxidation in mice by hexavalent chromium and its relation to the toxicity.
Nihon juigaku zasshi. The Japanese journal of veterinary science, Volume: 51, Issue: 6
1989
Involvement of intracellular iron in the toxicity of oxidized low density lipoprotein to cultured endothelial cells.
Biochemistry international, Volume: 22, Issue: 3
1990
Measurement of doxorubicin-induced lipid peroxidation under the conditions that determine cytotoxicity in cultured tumor cells.
Analytical biochemistry, Volume: 201, Issue: 2
1992
Prooxidant properties of 5-aminosalicylic acid. Possible mechanism for its adverse side effects.
Digestive diseases and sciences, Volume: 37, Issue: 9
1992
The role of lipid peroxidation in the nephrotoxicity of cisplatin.
Biochemical pharmacology, Sep-25, Volume: 44, Issue: 6
1992
Nitrofurantoin-induced pulmonary toxicity. In vivo evidence for oxidative stress-mediated mechanisms.
Biochemical pharmacology, Mar-03, Volume: 43, Issue: 5
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (2)

ArticleYear
Antioxidant status in rats after long-term intake of anthocyanins and ellagitannins from blackberries.
Journal of the science of food and agriculture, Volume: 91, Issue: 3
2011
Effects of acute and sub-chronic administration of iron nitrilotriacetate in the rat.
Toxicology, Volume: 59, Issue: 1
1989
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (3)

ArticleYear
Bioavailability study of a polyphenol-enriched extract from Hibiscus sabdariffa in rats and associated antioxidant status.
Molecular nutrition & food research, Volume: 56, Issue: 10
2012
[Effect of magnetic nanoparticles Fe3O4 on viability, attachment and spreading of cells isolated from fetuses and new-born rats].
Tsitologiia, Volume: 53, Issue: 4
2011
eNOS gene T-786C polymorphism modulates atorvastatin-induced increase in blood nitrite.
Free radical biology & medicine, Oct-01, Volume: 41, Issue: 7
2006
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (15)

ArticleYear
Survey on the effects of electron beam irradiation on chemical quality and sensory properties on quail meat.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, Volume: 112
2018
D-α-tocopheryl polyethylene glycol 1000 succinate-containing vehicles provide no detectable chemoprotection from oxidative damage.
Journal of applied toxicology : JAT, Volume: 35, Issue: 7
2015
Effect of superoxide dismutase and allopurinol on impulse noise-exposed guinea pigs--electrophysiological and biochemical study.
Acta oto-laryngologica, Volume: 123, Issue: 7
2003
Lipid peroxidation in liver of rats administrated with methyl mercuric chloride.
Biological trace element research, Volume: 54, Issue: 1
1996
Evaluation of Geriforte, an herbal geriatric tonic, on antioxidant defense system in Wistar rats.
Annals of the New York Academy of Sciences, Jun-30, Volume: 717
1994
Susceptibility of plasma low density lipoprotein to cupric ion-induced peroxidation in patients with variant angina.
Journal of the American College of Cardiology, Volume: 26, Issue: 3
1995
Effect of pretreatment with cimetidine or phenobarbital on lipoperoxidation in carbon tetrachloride- and trichloroethylene-dosed rats.
Toxicology, Volume: 38, Issue: 1
1986
Sex-related differences in NADPH-dependent lipid peroxidation induced by cadmium.
Archives of toxicology, Volume: 59, Issue: 3
1986
Lipoperoxides in plasma as measured by liquid-chromatographic separation of malondialdehyde-thiobarbituric acid adduct.
Clinical chemistry, Volume: 33, Issue: 2 Pt 1
1987
Comparison of the antioxidant properties of alpha-tocopherol and alpha-tocopheryl acetate in newborn rabbit lung.
Developmental pharmacology and therapeutics, Volume: 10, Issue: 4
1987
Hepatic lipid peroxidation in CoCl2-treated rats, evidenced by elevated concentrations of thiobarbituric acid chromogens.
Research communications in chemical pathology and pharmacology, Volume: 59, Issue: 1
1988
Effects of acute and sub-chronic administration of iron nitrilotriacetate in the rat.
Toxicology, Volume: 59, Issue: 1
1989
Iron-dependent peroxidation of rat brain: a regional study.
Journal of neuroscience research, Volume: 26, Issue: 2
1990
Effects of dietary pantethine levels on contents of fatty acids and thiobarbituric acid reactive substances in the liver of rats orally administered varying amounts of autoxidized linoleate.
Journal of nutritional science and vitaminology, Volume: 37, Issue: 1
1991
UV-C irradiation-induced peroxidative degradation of microsomal fatty acids and proteins: protection by an extract of Ginkgo biloba (EGb 761).
Free radical biology & medicine, Volume: 13, Issue: 3
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (2)

ArticleYear
Effect of 10 MeV E-beam irradiation combined with vacuum-packaging on the shelf life of Atlantic salmon fillets during storage at 4 °C.
Food chemistry, Feb-15, Volume: 145
2014
Development of antioxidant packaging material by applying corn-zein to LLDPE film in combination with phenolic compounds.
Journal of food science, Volume: 77, Issue: 10
2012
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]