Compounds > citrazinic acid
Page last updated: 2024-12-05

citrazinic acid

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

Description

Citrazinic acid, also known as 2,6-dihydroxyisonicotinic acid, is a heterocyclic organic compound with the molecular formula C6H5NO4. It is a white solid that is soluble in water and ethanol. Citrazinic acid is a natural product found in various plants, such as tea, coffee, and rice. It has been reported to exhibit a range of biological activities, including antioxidant, anti-inflammatory, and anti-cancer effects. The compound has also been investigated for its potential use as a therapeutic agent in the treatment of neurological disorders, such as Alzheimer's disease. Citrazinic acid has been synthesized through various methods, including the oxidation of pyrazines, the reaction of cyanoacetic acid with ethyl acetoacetate, and the hydrolysis of citrazinic acid amide. The compound's antioxidant properties have been attributed to its ability to scavenge free radicals and protect cells from oxidative damage. Citrazinic acid has also been shown to inhibit the production of pro-inflammatory cytokines, such as TNF-α and IL-6, suggesting its potential as an anti-inflammatory agent. Research on citrazinic acid continues to explore its therapeutic potential in various areas of medicine, including neurology, oncology, and immunology.'

citrazinic acid: inhibits 3-dehydroquinate dehydratase from Mycobacterium tuberculosis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID7425
CHEMBL ID2048371
CHEBI ID184700
SCHEMBL ID8957131
SCHEMBL ID185046
MeSH IDM0559884

Synonyms (63)

Synonym
BB 0242402
4-pyridinecarboxylic acid,2-dihydro-6-hydroxy-2-oxo-
99-11-6
2,6-dihydroxyisonicotinate
nsc-5214
2,6-dihydroxy-4-pyridinecarboxylic acid
isonicotinic acid,6-dihydroxy-
nsc5214
citrazinic acid
4-pyridinecarboxylic acid,6-dihydroxy-
2,6-dihydroxyisonicotinic acid
2,6-dihydroxy-4-carboxypyridine
wln: t6nj bq dvq fq
nsc-41334
4-pyridinecarboxylic acid, 1,2-dihydro-6-hydroxy-2-oxo-
kyselina citrazinova [czech]
isonicotinic acid, 1,2-dihydro-6-hydroxy-2-oxo-
isonicotinic acid, 2,6-dihydroxy-
einecs 202-731-2
4-pyridinecarboxylic acid, 2,6-dihydroxy-
OPREA1_725973
6-hydroxy-4-carboxy-2-pyridone
nsc 41334
2,6-dihydroxypyridine-4-carboxylic acid, 97%
MAYBRIDGE4_003590
2,6-dihydroxypyridine-4-carboxylic acid
STK378282
HMS1531D04
AKOS000301520
AKOS000114790
2-hydroxy-6-oxo-1h-pyridine-4-carboxylic acid
CHEBI:184700
A845964
BBL004463
6-hydroxy-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid
2,6-dihydroxy-isonicotinic acid (citrazinic acid)
n8q4xfv86a ,
kyselina citrazinova
unii-n8q4xfv86a
FT-0610664
2,6-dihydroxy-isonicotinic acid
AM20070173
AE-562/40806835
AB00673
CHEMBL2048371
BP-30063
SCHEMBL8957131
SCHEMBL185046
1,2-dihydro-6-hydroxy-2-oxo-4-pyridinecarboxylic acid
citrazinic acid [mi]
DTXSID3059185
W-100050
BS-3855
6-hydroxy-2-oxo-1,2-dihydro-4-pyridinecarboxylic acid #
isonicotinic acid, 2,6-dihydroxy-,
mfcd00006274
6-hydroxy-2-oxo-1,2-dihydropyridine-4-carboxylic acid
F2191-0236
citrazinc acid
Q5122816
EN300-00809
CS-0067136
Z56855768
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
aromatic carboxylic acidAny carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
[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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID670861Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 assessed as minimum concentration required to inhibit 90% growth after 1 week by fluorescence-based microplate Alamar Blue assay2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents.
AID670863Cytotoxicity against african green monkey Vero cells after 72 hrs by MTS assay2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents.
AID670862Antitubercular activity against non-replicating Mycobacterium tuberculosis assessed as minimum concentration required to inhibit 90% growth after 10 days under anaerobic condition by luciferase-based low-oxygen recovery assay2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (100.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.68

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

MetricThis Compound (vs All)
Research Demand Index35.68 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index39.83 (26.88)
Search Engine Supply Index1.91 (0.95)

This Compound (35.68)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.0710carbohydrazideantitubercular agent;
drug allergen
quinic acid
(-)-quinic acid : The (-)-enantiomer of quinic acid.		2.0610
shikimic acid
Shikimic Acid: A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.. shikimic acid : A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and microorganisms.		2.1110alpha,beta-unsaturated monocarboxylic acid;
cyclohexenecarboxylic acid;
hydroxy monocarboxylic acid		Escherichia coli metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
2-oxo-1,2-dihydroquinoline-4-carboxylic acid
[no description available]		2.0710quinolinemonocarboxylic acid
moxifloxacin
Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.		2.0710aromatic ether;
cyclopropanes;
fluoroquinolone antibiotic;
pyrrolidinopiperidine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.0710cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
pyrimidinones
Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.		2.0710
ConditionIndicatedRelationship StrengthStudiesTrials
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610