Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H4N2O4 |
Molecular Weight | 156.0963 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC(=O)NC(=O)N1
InChI
InChIKey=PXQPEWDEAKTCGB-UHFFFAOYSA-N
InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
Orotic acid is a minor dietary constituent. Historically it was believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin and is synthesized in the body, where it arises as an intermediate in the pathway for the synthesis of pyrimidine nucleotides. Orotic acid is converted to UMP by UMP synthase, a multifunctional protein with both orotate phosphoribosyl transferase and orotidylate decarboxylase activity. The most frequently observed inborn error of pyrimidine nucleotide synthesis is a mutation of the multifunctional protein UMP synthase. As a result, plasma orotic acid accumulates to high concentrations, and increased quantities appear in the urine. Orotic acid levels are elevated in the urea cycle defects ornithine transcarbamylase (OTC) deficiency, citrullinemia and argininosuccinic acidemia, as well as the mitochondrial transport disorder hyperornithinemia-hyperammonemia-homocitrullinuria (HHH) syndrome. Orotic acid is also elevated in hereditary orotic aciduria, or uridine monophosphate synthase deficiency, an autosomal recessive disorder characterized by megaloblastic anemia and crystalluria. In addition, orotic acid in combination with leflunomide is in the phase II of clinical trial to evaluate the clinical efficacy and safety of a combination in kidney transplant patients with high levels of Polyoma BK viruria for the purpose of preventing polyoma BK viremia and nephropathy, that could lead to kidney transplant loss from viral damage, acute rejection or both.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P11172|||Q9UG49 Gene ID: 7372.0 Gene Symbol: UMPS Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26059769 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Enzymic synthesis and breakdown of a pyrimidine, orotic acid. I. Dihydro-orotic dehydrogenase. | 1953 Sep-Oct |
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Optimization of allopurinol challenge: sample purification, protein intake control, and the use of orotidine response as a discriminative variable improve performance of the test for diagnosing ornithine carbamoyltransferase deficiency. | 1999 Jul |
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Effect of hesperetin, a citrus flavonoid, on the liver triacylglycerol content and phosphatidate phosphohydrolase activity in orotic acid-fed rats. | 2001 |
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Specific inhibition of a family 1A dihydroorotate dehydrogenase by benzoate pyrimidine analogues. | 2001 Aug 30 |
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Laboratory evaluation of urea cycle disorders. | 2001 Jan |
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Dihydrooxonate is a substrate of dihydroorotate dehydrogenase (DHOD) providing evidence for involvement of cysteine and serine residues in base catalysis. | 2001 Jul 15 |
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Simple gas chromatographic-mass spectrometric procedure for diagnosing pyrimidine degradation defects for prevention of severe anticancer side effects. | 2001 Jul 5 |
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Regulation of Cyp1a1 induction by dioxin as a function of cell cycle phase. | 2001 Nov |
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The interaction of 5-fluoroorotic acid with transition metals: synthesis and characterisation of Ni(II), Cu(II) and Zn(II) complexes. | 2002 Apr 28 |
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Capillary electrophoresis for detection of inherited disorders of purine and pyrimidine metabolism: a selective approach. | 2002 Feb |
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Effects of fatty liver induced by niacin-free diet with orotic acid on the metabolism of tryptophan to niacin in rats. | 2002 Jun |
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A new type of dihydroorotate dehydrogenase, type 1S, from the thermoacidophilic archaeon Sulfolobus solfataricus. | 2002 Jun |
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Mapping the active site-ligand interactions of orotidine 5'-monophosphate decarboxylase by crystallography. | 2002 Mar 26 |
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Development of a CE method to analyze organic acids in dairy products: application to study the metabolism of heat-shocked spores. | 2002 Mar 27 |
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An investigation of orotic acid levels in the breastmilk of smoking and non-smoking mothers. | 2002 Oct |
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Allopurinol challenge tests performed before and after living-related donor liver transplantation in citrullinaemia. | 2003 |
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Microarray analysis of orthologous genes: conservation of the translational machinery across species at the sequence and expression level. | 2003 |
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Effect of PSC 833, an inhibitor of P-glycoprotein, on 1,2-dimethylhydrazine-induced liver carcinogenesis in rats. | 2003 Dec |
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Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. | 2003 Jul 15 |
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Comprehensive study of the luminescent properties and lifetimes of Eu(3+) and Tb(3+) chelated with various ligands in aqueous solutions: influence of the synergic agent, the surfactant and the energy level of the ligand triplet. | 2003 Jun |
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Crystallization and preliminary X-ray crystallographic analysis of orotate phosphoribosyltransferase from Helicobacter pylori. | 2003 Jun 30 |
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Both gene expression for orotate phosphoribosyltransferase and its ratio to dihydropyrimidine dehydrogenase influence outcome following fluoropyrimidine-based chemotherapy for metastatic colorectal cancer. | 2003 Oct 20 |
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Purine and pyrimidine metabolites in children's urine. | 2003 Sep |
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How reliable is the allopurinol load in detecting carriers for ornithine transcarbamylase deficiency? | 2004 |
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Regulation of pyrimidine nucleotide formation in Pseudomonas reptilivora. | 2004 |
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An integrated reverse functional genomic and metabolic approach to understanding orotic acid-induced fatty liver. | 2004 Apr 13 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01620268
Daily dose of leflunomide adjusted to target steady state blood levels of 50 ug/mL to 100 ug/mL of the active metabolite plus 600 mg orotic acid
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1036347
By means of electron microscopic and quantitative methods at the explantate cultures of the fetal hippocampus in vitro the influence of the orotic acid, sodium orotate and methylglucamine orotate on the neurogenesis was investigated. After three days of the in vitro cultivation the neuroblasts influenced by these drugs show a smaller respectively not different degree of differentiation compared to the controls. Under the influence of the orotic acid and of its derivatives the neurogenesis is significantly stimulated. The drugs produce a significant increase of the membrane-bound ribosomes and polysomes. The total number of ribosomes increases following the application of orotic acid by 20%, of sodium-orotate by 48% and of methylglucamine-orotate by 23% compared to the controls (alpha = 0,1%). Sodium-orotate shows with reference to the neuronal development the clearest stimulatory effect. After 20 days in vitro the total number of ribosomes is by 60% higher at the treated cultures than in the controls. The results might suggest, that an enlarged supply of the pyrimidine nucleotide via a raising of the RNA- and the protein synthesis might stimulate the development of the neuroblasts even under the in vitro conditions.
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DSLD |
1822 (Number of products:5)
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NCI_THESAURUS |
C45812
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C81628
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m8242
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100000083330
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7712
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OROTIC ACID
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