5-nitrouracil profile

5-Nitrouracil is a synthetic compound that is an analog of uracil. It is a potent inhibitor of thymidylate synthase, an enzyme that is essential for the synthesis of thymine, a key component of DNA. This inhibition leads to the depletion of thymine nucleotides, which can disrupt DNA replication and ultimately cell proliferation. 5-Nitrouracil has been studied as a potential anticancer agent, particularly for the treatment of solid tumors. It has also been investigated for its potential to suppress the immune system, making it a potential therapeutic target for autoimmune diseases. The compound is typically synthesized via the nitration of uracil, a reaction that involves the introduction of a nitro group (-NO2) onto the uracil molecule. Research on 5-nitrouracil continues to explore its potential in various therapeutic applications and its impact on biological systems.'

5-nitrouracil: prevents thymidine degradation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-nitrouracil : A C-nitro compound consisting of uracil having a nitro group at the 5-position. [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]

ID Source	ID
PubMed CID	69135
CHEMBL ID	323780
CHEBI ID	60763
SCHEMBL ID	190925
SCHEMBL ID	5780473
MeSH ID	M0160755

Synonym
nsc 9790
ai3-25473
einecs 210-250-4
5-nitropyrimidine-2,4-diol
AKOS002337367
AKOS002722690
2,4-dihydroxy-5-nitropyrimidine
5-nitro-1h-pyrimidine-2,4-dione
2,4(1h,3h)-pyrimidinedione, 5-nitro-
uracil, 5-nitro-
2,3h)-pyrimidinedione, 5-nitro-
nsc9790
nsc-9790
5-nitrouracil
611-08-5
5-nitrouracil, 98%
SR-01000390728-2
STK336423
5-nitropyrimidine-2,4(1h,3h)-dione
AKOS000399747
CHEBI:60763 ,
CHEMBL323780
N0281
STK633437
A8490
5-nitropyrimidine-2,4-diol;5-nitrouracil
5nu ,
CCG-50731
EPITOPE ID:138112
F0848-0340
4-hydroxy-5-nitropyrimidin-2(1h)-one
FT-0620726
STL336705
F0017-1804
BBL033938
AKOS022142015
AM83914
SCHEMBL190925
SCHEMBL5780473
DTXSID2060597
Q-200549
661-08-5
5-nitro-2,4(1h,3h)-pyrimidinedione #
AC-907/30002012
5-nitro-2,4(1h,3h)-pyrimidinedione
AKOS025293373
5-nitro-1,2,3,4-tetrahydropyrimidine-2,4-dione
STR04133
2,4(1h,3h)-pyrimidinedione-5-nitro
AC-23094
mfcd00006021
SR-01000390728-1
sr-01000390728
Z274568144
5-nitrouracil, 97%
SY001470
5-nitro-2.6-dioxypyrimidin
CS-W017981
Q27128575
furfurylthioacetate
EN300-73335
5-nitro-2,4-dihydroxypyrimidine

Class	Description
C-nitro compound	A nitro compound having the nitro group (-NO2) attached to a carbon atom.
[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]

Assay ID	Title	Year	Journal	Article
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal of biomolecular screening, Jul, Volume: 21, Issue:6	A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).	2014	Journal of biomolecular screening, Jul, Volume: 19, Issue:6	A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808	Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID216186	The compound was tested for antiviral activity against Herpes simplex virus type-1 in the vero cells using plaque inhibition assay; no IC50 reached without damage to the cell monolayer.	1999	Journal of medicinal chemistry, Aug-26, Volume: 42, Issue:17	Virtual combinatorial syntheses and computational screening of new potential anti-herpes compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (20.00)	18.7374
1990's	4 (26.67)	18.2507
2000's	1 (6.67)	29.6817
2010's	4 (26.67)	24.3611
2020's	3 (20.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	16 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
adipic acid adipic acid : An alpha,omega-dicarboxylic acid that is the 1,4-dicarboxy derivative of butane.	2	1	alpha,omega-dicarboxylic acid; dicarboxylic fatty acid	food acidity regulator; human xenobiotic metabolite
orotic acid Orotic Acid: An intermediate product in PYRIMIDINE synthesis which plays a role in chemical conversions between DIHYDROFOLATE and TETRAHYDROFOLATE.. orotic acid : A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.	2	1	pyrimidinemonocarboxylic acid	Escherichia coli metabolite; metabolite; mouse metabolite
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	1.98	1	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
thymine [no description available]	1.97	1	pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite
uracil 2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder	3.79	11	pyrimidine nucleobase; pyrimidone	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; prodrug; Saccharomyces cerevisiae metabolite
fluorouracil Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.	2.42	2	nucleobase analogue; organofluorine compound	antimetabolite; antineoplastic agent; environmental contaminant; immunosuppressive agent; radiosensitizing agent; xenobiotic
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.1	1	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
phenolphthalein Phenolphthalein: An acid-base indicator which is colorless in acid solution, but turns pink to red as the solution becomes alkaline. It is used medicinally as a cathartic.	1.98	1	phenols
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.	2.1	1	benzoic acids; sulfonamide	uricosuric drug
sulfinpyrazone Sulfinpyrazone: A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.	2.52	2	pyrazolidines; sulfoxide	uricosuric drug
thymidine [no description available]	2.9	4	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
floxuridine Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.	1.97	1	nucleoside analogue; organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; radiosensitizing agent
cordycepin [no description available]	2	1	3'-deoxyribonucleoside; adenosines	antimetabolite; nucleoside antibiotic
formaldoxime formaldoxime: structure in first source. nitrone : A nitrogen ylide obtained by oxygenation of any imine.	2	1
tropine [no description available]	2	1
5-nitrobarbituric acid [no description available]	2	1
deoxyuridine [no description available]	2	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
naftalofos naftalofos: structure	2.1	1	organic heterotricyclic compound	anthelminthic drug
capecitabine Capecitabine: A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER.. capecitabine : A carbamate ester that is cytidine in which the hydrogen at position 5 is replaced by fluorine and in which the amino group attached to position 4 is converted into its N-(penyloxy)carbonyl derivative. Capecitabine is a antineoplastic agent used in the treatment of cancers.	7.25	1	carbamate ester; cytidines; organofluorine compound	antimetabolite; antineoplastic agent; prodrug
nebularine nebularine: structure. nebularine : A purine ribonucleoside that is 9H-purine attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage.	2	1	purine ribonucleoside; purines D-ribonucleoside	fungal metabolite
5-methylcytidine [no description available]	2	1	methylcytidine
4,4'-azobis(phenol) 4,4'-azobis(phenol): isolated from fungus Agaricus xanthodermus; structure given in first source	2	1
7-hydroxycoumarin 7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.	2	1	hydroxycoumarin	fluorescent probe; food component; plant metabolite
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	2	1	ammonium salt; inorganic sulfate salt	fertilizer
nitrofurantoin Nitrofurantoin: A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression.. nitrofurantoin : An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.	2	1	imidazolidine-2,4-dione; nitrofuran antibiotic; organonitrogen heterocyclic antibiotic; organooxygen heterocyclic antibiotic	antibacterial drug; antiinfective agent; hepatotoxic agent
chlorantranilipole chlorantranilipole: anthranilic diamide insecticide.that disrupts mating in codling moth (Lepidoptera: Tortricidae). chlorantraniliprole : A carboxamide resulting from the formal condensation of the carboxylic acid group of 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid with the primary amino group of 2-amino-5-chloro-N,3-dimethylbenzamide. The first of the anthranilic diamide insecticides, it is a ryanodine receptor activator and is used to protect a wide variety of crops, including corn, cotton, grapes, rice and potatoes.	2.15	1	monochlorobenzenes; organobromine compound; pyrazole insecticide; pyrazoles; pyridines; secondary carboxamide	ryanodine receptor agonist
dextrothyroxine [no description available]	2.25	1
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	1.98	1
inosine [no description available]	2	1	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite

Condition	Relationship Strength	Studies
Plasmodium falciparum Malaria [description not available]	2.1	1
Malaria, Falciparum Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.	2.1	1
Anemia, Fanconi [description not available]	2.13	1
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.13	1
Colorectal Cancer [description not available]	7.25	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.25	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2	1
Rheumatoid Arthritis [description not available]	1.97	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	1.97	1

5-nitrouracil

Description

Cross-References

Synonyms (62)

Drug Classes (1)

Bioassays (4)

Research

Studies (15)

Market Indicators

Research Demand Index: 20.10

Study Types