Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C5H3N2O4.Mg |
Molecular Weight | 334.4816 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Mg++].[O-]C(=O)C1=CC(=O)NC(=O)N1.[O-]C(=O)C2=CC(=O)NC(=O)N2
InChI
InChIKey=QWLHYYKDLOVBNV-UHFFFAOYSA-L
InChI=1S/2C5H4N2O4.Mg/c2*8-3-1-2(4(9)10)6-5(11)7-3;/h2*1H,(H,9,10)(H2,6,7,8,11);/q;;+2/p-2
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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Media formulations for various two-hybrid systems. | 2001 |
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Insight into the chemistry of flavin reduction and oxidation in Escherichia coli dihydroorotate dehydrogenase obtained by rapid reaction studies. | 2001 Apr 10 |
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Pitfalls in the detection of heterozygosity by allopurinol in a variant form of ornithine carbamoyltransferase deficiency. | 2001 Aug |
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Specific inhibition of a family 1A dihydroorotate dehydrogenase by benzoate pyrimidine analogues. | 2001 Aug 30 |
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Theoretical studies of mechanisms and kinetic isotope effects on the decarboxylation of orotic acid and derivatives. | 2001 Dec 5 |
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Ornithine carbamoyltransferase deficiency: improved sensitivity of testing for protein tolerance in the diagnosis of heterozygotes. | 2001 Feb |
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Multiple inhibitor analysis of the brequinar and leflunomide binding sites on human dihydroorotate dehydrogenase. | 2001 Feb 20 |
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Large-scale production of the carbohydrate portion of the sialyl-Tn epitope, alpha-Neup5Ac-(2-->6)-D-GalpNAc, through bacterial coupling. | 2001 Feb 28 |
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Intra-day variations in urinary pyrimidines in ornithine carbamoyltransferase deficiency and healthy individuals. | 2001 Jun |
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Molecular structure of dihydroorotase: a paradigm for catalysis through the use of a binuclear metal center. | 2001 Jun 19 |
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Contribution of the bacterial endosymbiont to the biosynthesis of pyrimidine nucleotides in the deep-sea tube worm Riftia pachyptila. | 2001 Jun 29 |
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Rapid selection against truncation mutants in yeast reverse two-hybrid screens. | 2001 May |
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Capillary zone electrophoresis of orotic acid in urine with on-line isotachophoresis sample pretreatment and diode array detection. | 2001 May 4 |
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Isolation of mitochondria from Plasmodium falciparum showing dihydroorotate dependent respiration. | 2001 Nov |
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Evolution: constantly avoiding mutation. | 2001 Nov 13 |
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Orotic acid added to casein, but not to egg protein, soy protein, or wheat gluten diets increases 1,2-diacylglycerol levels and lowers superoxide dismutase activities in rat liver. | 2001 Oct |
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Regulation of pyrimidine synthesis in Pseudomonas mendocina. | 2002 |
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[Orotic acid as a metabolic agent]. | 2002 |
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Control of pyrimidine formation in Pseudomonas putida ATCC 17536. | 2002 Dec |
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N-acetylglutamate synthase deficiency and the treatment of hyperammonemic encephalopathy. | 2002 Dec |
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The oral anti-volatile sulphur compound effects of zinc salts and their stability constants. | 2002 Feb |
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Transcriptional cosuppression of yeast Ty1 retrotransposons. | 2002 Feb 15 |
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Flumazenil responsive ornithine transcarbamylase deficiency encephalopathy: clinical and radiographic features. | 2002 Jan |
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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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Behavior of alginate gel beads containing chitosan salt prepared with water-soluble vitamins. | 2002 Mar |
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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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The dimeric dihydroorotate dehydrogenase A from Lactococcus lactis dissociates reversibly into inactive monomers. | 2002 Nov |
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Malarial dihydroorotate dehydrogenase. Substrate and inhibitor specificity. | 2002 Nov 1 |
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Equilibrium of formation of the 6-carbanion of UMP, a potential intermediate in the action of OMP decarboxylase. | 2002 Nov 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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Influence of carbon source on pyrimidine synthesis in Pseudomonas mendocina. | 2003 |
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Rapid determination of orotic acid in urine by a fast liquid chromatography/tandem mass spectrometric method. | 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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Lactococcus lactis dihydroorotate dehydrogenase A mutants reveal important facets of the enzymatic function. | 2003 Aug 1 |
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Experimental evidence for the existence of the passive antitumor defense system formed by the synergistic action of certain small substances of the circulatory system. | 2003 Dec |
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Plasma urea-cycle-related amino acids, ammonium levels, and urinary orotic acid excretion in short-bowel patients managed with an oral diet. | 2003 Feb |
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Quantification of non-protein nitrogen components of infant formulae and follow-up milks: comparison with cows' and human milk. | 2003 Jul |
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Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. | 2003 Jul 15 |
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Magnesium-orotate supplementation for idiopathic infertile male patients: a randomized, placebo-controlled clinical pilot study. | 2003 Jun |
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Influence of dietary arginine on sexual dimorphism of arginine metabolism in mice. | 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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Involvement of voltage- and ligand-gated Ca2+ channels in the neuroexcitatory and synergistic effects of putative uremic neurotoxins. | 2003 May |
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Cloning and disruption of the PpURA5 gene and construction of a set of integration vectors for the stable genetic modification of Pichia pastoris. | 2003 Nov |
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High-resolution diffusion and relaxation-edited magic angle spinning 1H NMR spectroscopy of intact liver tissue. | 2003 Nov |
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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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pdf1, a palmitoyl protein thioesterase 1 Ortholog in Schizosaccharomyces pombe: a yeast model of infantile Batten disease. | 2004 Apr |
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Inhibitor binding in a class 2 dihydroorotate dehydrogenase causes variations in the membrane-associated N-terminal domain. | 2004 Apr |
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Modest catalysis of the decarboxylation of orotate by hydrogen bonding: a theoretical model for orotidine- 5' -monophosphate decarboxylase. | 2004 Apr |
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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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WHO-VATC |
QA12CC09
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WHO-ATC |
A12CC09
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4594
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GI96W46M5A
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C87337
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DTXSID20905129
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252-167-6
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SUB03037MIG
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C104468
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139233
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CHEMBL3707282
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Magnesium orotate
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C1505
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GI96W46M5A
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DB13786
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3036905
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ACTIVE MOIETY
SUBSTANCE RECORD