Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H4N4O |
Molecular Weight | 136.1115 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC=NC2=C1N=CN2
InChI
InChIKey=FDGQSTZJBFJUBT-UHFFFAOYSA-N
InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
Molecular Formula | C5H4N4O |
Molecular Weight | 136.1115 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB04076Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26196868 | https://www.ncbi.nlm.nih.gov/pubmed/17149876 | https://www.ncbi.nlm.nih.gov/pubmed/25956679 | https://www.ncbi.nlm.nih.gov/pubmed/28238512 | https://www.ncbi.nlm.nih.gov/pubmed/3670521
Sources: https://www.drugbank.ca/drugs/DB04076
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26196868 | https://www.ncbi.nlm.nih.gov/pubmed/17149876 | https://www.ncbi.nlm.nih.gov/pubmed/25956679 | https://www.ncbi.nlm.nih.gov/pubmed/28238512 | https://www.ncbi.nlm.nih.gov/pubmed/3670521
Hypoxanthine is a naturally occurring purine derivative and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway. Hypoxanthine is a necessary additive in the certain cell, bacteria, and parasite cultures as a substrate and nitrogen source. For example, it is commonly a required reagent in malaria parasite cultures, since Plasmodium falciparum requires a source of hypoxanthine for nucleic acid synthesis and energy metabolism.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17149876 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Is skeletal muscle damaged by the oxidative stress following anaerobic exercise? | 2001 |
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The mechanism of switching among multiple BER pathways. | 2001 |
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Base excision repair in nuclear and mitochondrial DNA. | 2001 |
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Identification of a new point mutation in the human xanthine dehydrogenase gene responsible for a case of classical type I xanthinuria. | 2001 Apr |
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DNA triple-helix formation at pyrimidine-purine inversion sites. | 2001 Apr-Jul |
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Unaltered apoptotic behaviour of mononuclear cells from patients with sporadic Creutzfeldt-Jakob disease. | 2001 Aug |
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Isolation and characterization of the Xanthine dehydrogenase gene of the Mediterranean fruit fly, Ceratitis capitata. | 2001 Aug |
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Pyruvate improves cerebral metabolism during hemorrhagic shock. | 2001 Aug |
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Structure-activity relationships and inhibitory effects of various purine derivatives on the in vitro growth of Plasmodium falciparum. | 2001 Aug 1 |
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L-tyrosine and nitric oxide synergize to prevent cytotoxic effects of superoxide. | 2001 Aug 28 |
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Reaction of superoxide and nitric oxide with peroxynitrite. Implications for peroxynitrite-mediated oxidation reactions in vivo. | 2001 Aug 3 |
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Sudden infant death syndrome (SIDS): T-cell immunodeficiency--Part 1. | 2001 Feb |
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Protection of the rat liver against rewarming ischemic injury by University of Wisconsin solution. | 2001 Feb |
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Study of the interaction of cis-dichloro-(1,2 diethyl-3-aminopyrrolidine)Pt(II) complex with poly(I), poly(C) and poly(I) x poly(C). | 2001 Jul |
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Random amplified ribosomal DNA restriction analysis for rapid identification of thermophilic Actinomycete-like bacteria involved in hypersensitivity pneumonitis. | 2001 Jul |
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The effect of allopurinol on focal cerebral ischaemia: an experimental study in rabbits. | 2001 Jul |
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Separation of inosine, hypoxanthine, and guanosine by high-performance liquid chromatography on silica. | 2001 Jul |
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In vitro and in vivo properties of novel nucleoside transport inhibitors with improved pharmacological properties that potentiate antifolate activity. | 2001 Jul |
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Middle cerebral artery occlusion and reperfusion in primates monitored by microdialysis and sequential positron emission tomography. | 2001 Jul |
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Nitric oxide- and nitric oxide donors-induced relaxation and its modulation by oxidative stress in piglet pulmonary arteries. | 2001 Jul |
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Sudden infant death syndrome Part 2: the response of the reticuloendothelial system to hypoxemia and infection. | 2001 Jul |
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Purine salvage to adenine nucleotides in different skeletal muscle fiber types. | 2001 Jul |
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Investigation of the functional role of active site loop II in a hypoxanthine phosphoribosyltransferase. | 2001 Jul 27 |
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Antiplasmodial and antioxidant isofuranonaphthoquinones from the roots of Bulbine capitata. | 2001 Jun |
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Altered purine nucleotide degradation during exercise in patients with essential hypertension. | 2001 Jun |
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Changes in serum hypoxanthine levels by exercise in obese subjects. | 2001 Jun |
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[Biochemical parameters predictive of neuronal damage in childhood]. | 2001 Jun 16-30 |
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Resveratrol suppresses hepatoma cell invasion independently of its anti-proliferative action. | 2001 Jun 26 |
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Superoxide potently induces ceramide formation in glomerular endothelial cells. | 2001 Jun 8 |
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[Two cases of exercise-induced acute renal failure with idiopathic renal hypouricemia]. | 2001 May |
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Adenine deaminase activity of the yicP gene product of Escherichia coli. | 2001 May |
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Oxidative stress impairs insulin internalization in endothelial cells in vitro. | 2001 May |
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Hepatic xanthine levels as viability predictor of livers procured from non-heart-beating donor pigs. | 2001 May 15 |
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[Post-radiation changes in kinetic parameters of purine-catabolizing enzymes in rat blood serum after combined action of external and internal irradiation caused by 137Cs]. | 2001 May-Jun |
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[Polymethylene derivatives of nucleic bases with omega-functional groups. II. Adenine and hypoxanthine derivatives]. | 2001 May-Jun |
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Off-pump versus on-pump coronary artery bypass grafting: oxidative stress and renal function. | 2001 Nov |
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Inhibitory effects of methylxanthines on the pre-eclamptic-like symptoms in ewes. | 2001 Nov |
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Folate deficiency-induced oxidative stress and apoptosis are mediated via homocysteine-dependent overproduction of hydrogen peroxide and enhanced activation of NF-kappaB in human Hep G2 cells. | 2001 Oct |
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Addition of hypoxanthine to culture media allows in vitro cultivation of Babesia bovis and B. bigemina at reduced serum concentrations. | 2001 Oct |
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Effect of fenofibrate on plasma concentration and urinary excretion of purine bases and oxypurinol. | 2001 Oct |
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Effects of storage temperature and preservative treatment on shelf life of the pond-raised freshwater fish, silver perch (Bidyanus bidyanus). | 2001 Oct |
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Effect of norepinephrine on the urinary excretion of purine bases and oxypurinol. | 2001 Oct |
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Sperm disposal system in spermatic granuloma: a link with superoxide radicals. | 2001 Oct |
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Catabolism of exogenous deoxyinosine in cultured epithelial amniotic cells. | 2001 Oct 3 |
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Concentrations of nucleotides, nucleosides, purine bases, oxypurines, uric acid, and neuron-specific enolase in the cerebrospinal fluid of children with sepsis. | 2001 Sep |
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Early onset of lipid peroxidation after human traumatic brain injury: a fatal limitation for the free radical scavenger pharmacological therapy? | 2001 Sep |
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Newborn piglets with meconium aspiration resuscitated with room air or 100% oxygen. | 2001 Sep |
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Protein kinase C, rather than protein kinase A is involved in follicle-stimulating hormone-mediated meiotic resumption of mouse cumulus cell-enclosed oocytes in hypoxanthine-supplemented medium. | 2001 Sep |
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Molecular analysis of HPRT1(+) somatic cell hybrids derived from a carrier of an HPRT1 mutation responsible for Lesch-Nyhan syndrome. | 2001 Sep 15 |
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Synthesis and purine receptor affinity of 6-oxopurine nucleosides and nucleotides containing (N)-methanocarba-pseudoribose rings. | 2001 Sep 3 |
Patents
Sample Use Guides
2 μL of a solution of hypoxanthine (20 pmol/2 μL) or vehicle (saline 0.9 %) was administered in the right striatum of the rats 1 μL per minute.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15589795
The in vitro drug sensitivity of the Cambodian isolates was assessed by use of a classical isotopic 48- h test. fresh blood samples were washed three times with RPMI 1640 medium (GibcoTM, Invitrogen Corporation, France) by centrifugation (800×g, 10 min). The parasites were then tested directly without culture adaptation. The infected erythrocytes (1.5% hematocrit, 0.1–1% parasitemia) were suspended in complete RPMI medium supplemented with 10% of decomplemented human AB+ serum (Biomedia, France) and buffered with 25 mM/l Hepes and 25 mM/l NaHCO3. The mixture was distributed (200 mkl per well) into the 96-well test plates that had been pre-coated with antimalarial agents. Each plate included two drug-free control wells and one control well without parasites. The culture plates were incubated for 48 h at 37 ◦Cina5%CO2 atmosphere. [3H]Hypoxanthine (0.5 mkCi/well; Amersham Biosciences, France) was used to assess parasite growth. Each isolate was tested once in duplicate in the microplates with serial dilutions of drugs. Drug response was quantified by monitoring [3H]hypoxanthine uptake in aWallac MicroBeta Trilux counter (Perkin-Elmer, France). At the end of the incubation period, the plates were frozen at −20 ◦C and thawed to lyse the cells. After collection on glassfiber filter paper using a cell harvester, the amount of [3H]hypoxanthine incorporated into the parasites nucleoprotein was determined.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:09:52 UTC 2023
by
admin
on
Fri Dec 15 15:09:52 UTC 2023
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Record UNII |
2TN51YD919
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Record Status |
Validated (UNII)
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Record Version |
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LOINC |
2452-1
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75135-4
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75123-0
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2453-9
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17004-3
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NCI_THESAURUS |
C62554
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38366-1
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NCI_THESAURUS |
C786
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m6178
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DTXSID8045983
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2TN51YD919
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200-697-3
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68-94-0
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1191226
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17368
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HYPOXANTHINE
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C29105
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DB04076
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100000077634
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790
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D019271
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SUB14172MIG
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14665
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
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PARENT -> IMPURITY |
In the chromatogram obtained with solution (3) the area of any peak corresponding to impurity A (hypoxanthine) is not greater than the area of the principal peak obtained with solution (1) (0.5%).
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