Page last updated: 2024-12-05

barbituric acid

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

Description

barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active. [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 CID6211
CHEBI ID16294
SCHEMBL ID38707
MeSH IDM0100720

Synonyms (86)

Synonym
pyrimidinetrione
2,6-(1h,3h,5h)-pyrimidinetrione
nsc7889
nsc-7889
2,6-trioxohexahydropyrimidine
2,6(1h,3h,5h)-pyrimidinetrione
2,6-trihydroxypyrimidine
6-hydroxyuracil
urea,n'-(1,3-dioxo-1,3-propanediyl)-
2,6-pyrimidinetriol
2,4,6(1h,3h,5h)-pyrimidinetrione
malonylharnstoff
barbitursaeure
CHEBI:16294 ,
pyrimidine-2,4,6(1h,3h,5h)-trione
pyrimidinetriol
einecs 200-658-0
ai3-02724
hydrouracil, 6-hydroxy-
nsc 7889
barbituric acid (van)
1,2,3,4,5,6-hexahydro-2,4,6-pyrimidinetrione
urea, n,n'-(1,3-dioxo-1,3-propanediyl)-
2,4,6-trihydroxypyrimidine
2,4,6-trioxohexahydropyrimidine
2,4,6-pyrimidinetrione
hexahydropyrimidine-2,4,6-trione
inchi=1/c4h4n2o3/c7-2-1-3(8)6-4(9)5-2/h1h2,(h2,5,6,7,8,9
STK317809
barbituric acid
malonylurea
67-52-7
C00813
barbituric acid, reagentplus(r), 99%
4A0BDFFD-9542-4996-A89F-E5A55D03B250
AKOS000288853
BMSE000346
barbituric acid (van) (8ci)
1,3-diazinane-2,4,6-trione
A835792
NCGC00248877-01
dtxcid20129
tox21_200924
NCGC00258478-01
dtxsid8020129 ,
cas-67-52-7
B0003
b1063 ,
br8 ,
unii-wq92y2793g
wq92y2793g ,
ec 200-658-0
FT-0622555
EPITOPE ID:120355
fluorouracil impurity a [ep impurity]
barbituric acid [mi]
SCHEMBL38707
2,4,6-(1h,3h,5h)pyrimidinetrione
AKOS024255606
hexahydro-pyrimidine-2,4,6-trione
Q-200672
2,4,6-pyrimidinetrione(1h,3h,5h)
BS-3763
BBL036209
2-hydroxypyrimidine-4,6(1h,5h)-dione
STL451498
4,6-dihydroxy-2,5-dihydropyrimidin-2-one
F0001-1773
mfcd00006666
barbituric acid, for spectrophotometric det. of cyanide, >=99.5%
EN300-19230
fluorouracil impurity a, european pharmacopoeia (ep) reference standard
2,4,6(1h,3h,5h)-pyrimidinetrione (acd/name 4.0)
n,n'-(1,3-dioxo-1,3-propanediyl)-urea
nn'-(1,3-dioxo-1,3-propanediyl)-urea
barbitursaure
2,4,6-(1h,3h,5h)-pyrimidinetrione
CS-W018516
BCP21798
malonylurea;2,4,6(1h,3h,5h)-pyrimidinetrione;6-hydroxyuracil
Q410278
AMY237
pyrimidine-2
barbituric
2,4,6-pyrimidinetrione(1h,3h,5h)/
Z104473234

Research Excerpts

Effects

ExcerptReferenceRelevance
"Barbituric acid derivatives have been used as antiasthmatic drugs in the clinic."( Treatment with a New Barbituric Acid Derivative Exerts Antiproliferative and Antimigratory Effects against Sorafenib Resistance in Hepatocellular Carcinoma.
Chien, CY; Hsu, MH; Hsu, SM; Liao, YJ; Suk, FM; Wang, YH, 2020
)
1.6

Toxicity

ExcerptReferenceRelevance
" In addition to some kinds of adverse effects and specific toxicity (e."( PASS: identification of probable targets and mechanisms of toxicity.
Filimonov, D; Gloriozova, T; Lagunin, A; Poroikov, V; Zakharov, A,
)
0.13

Bioavailability

ExcerptReferenceRelevance
"3), the enzyme responsible for uridine catabolism, and 2',3',5'-tri-O-acetyluridine (TAU), a prodrug of uridine, were used to investigate the possibility of improving the bioavailability of oral uridine in mice."( 5-(m-Benzyloxybenzyl)barbituric acid acyclonucleoside, a uridine phosphorylase inhibitor, and 2',3',5'-tri-O-acetyluridine, a prodrug of uridine, as modulators of plasma uridine concentration. Implications for chemotherapy.
Ashour, OM; el Kouni, MH; Naguib, FN, 1996
)
0.61
" Intragastric administration of gentamicin (antibiotic poorly absorbed from the gastrointestinal tract) 2-fold reduced ammonium concentration in the caecal contents and prevented hyperammoniemia during induction of barbiturate coma."( Intensification of ammonium diffusion from rat gastrointestinal tract during acute barbiturate intoxication.
Ivnitsky, JJ; Rejniuk, VL; Schäfer, TV, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" Dosage below 25 mg."( A barbiturate antidote. Use of methylethyl-glutarmide in barbiturate intoxication and in terminating barbiturate anesthesia.
MARMER, MJ, 1959
)
0.24
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.03890.000229.305416,493.5996AID743075
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency27.30600.000323.4451159.6830AID743065
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

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]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1553462Cysteine reactivity assessed as cysteine oxidation2019Journal of medicinal chemistry, 06-27, Volume: 62, Issue:12
Emerging and Re-Emerging Warheads for Targeted Covalent Inhibitors: Applications in Medicinal Chemistry and Chemical Biology.
AID1130943Octanol-water partition coefficient, log P of nonionized form of compound1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
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.
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.
AID1130940Retention index of the compound by HPLC method1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Correlation of biological activity and high-pressure liquid chromatographic retention index for a series of propranolol, barbiturate, and anthranilic acid analogues.
AID1893771Inhibition of recombinant human QC using H-Gln-AMC hydrobromide as fluorogenic substrate incubated for 6 hrs by fluorometric microplate reader analysis2022ACS medicinal chemistry letters, Sep-08, Volume: 13, Issue:9
2-Amino-1,3,4-thiadiazoles as Glutaminyl Cyclases Inhibitors Increase Phagocytosis through Modification of CD47-SIRPα Checkpoint.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,364)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901117 (81.89)18.7374
1990's35 (2.57)18.2507
2000's74 (5.43)29.6817
2010's116 (8.50)24.3611
2020's22 (1.61)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 100.47

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index100.47 (24.57)
Research Supply Index7.31 (2.92)
Research Growth Index4.67 (4.65)
Search Engine Demand Index184.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (100.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (0.20%)5.53%
Reviews20 (1.34%)6.00%
Case Studies14 (0.94%)4.05%
Observational2 (0.13%)0.25%
Other1,448 (97.38%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]