Identification
- Summary
Orotic acid is a drug used to manage uncomplicated liver dysfunction in combination with xanthine.
- Generic Name
- Orotic acid
- DrugBank Accession Number
- DB02262
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Orotic acid (DB02262)
- Weight
- Average: 156.0963
Monoisotopic: 156.017106626 - Chemical Formula
- C5H4N2O4
- Synonyms
- Acido orotico
- Acidum oroticum
- Orotic acid
- Orotsäure
- Uracil-6-carboxylic acid
- Vitamin B13
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Hepatic dysfunction Combination Product in combination with: Xanthine (DB02134) •••••••••••• •••••••• •••••••••• •••••••• Used as adjunct in combination to treat Uncomplicated hepatic dysfunction Combination Product in combination with: Xanthine (DB02134) •••••••••••• •••••••• ••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UOrotate phosphoribosyltransferase Not Available Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720) UDihydroorotate dehydrogenase (quinone), mitochondrial Not Available Humans UDihydroorotate dehydrogenase (quinone) Not Available Escherichia coli (strain K12) UDihydroorotase inhibitorEscherichia coli (strain K12) UDihydroorotate dehydrogenase A (fumarate) Not Available Lactococcus lactis subsp. cremoris - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Pyrimidine Metabolism Metabolic MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy) Disease beta-Ureidopropionase Deficiency Disease Dihydropyrimidinase Deficiency Disease UMP Synthase Deficiency (Orotic Aciduria) Disease - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ATOXCYNAROL® INYECTABLE Orotic acid (12.5 mg) + Xanthine (12.5 mg) Solution Intramuscular ARBOFARMA S.A.S. 2010-12-16 2022-01-31 Colombia 
BETA - NECROTON CAPSULA Orotic acid (200 mg) + Xanthine (50 mg) Capsule, coated Oral Laboratorios Incobra S.A. 2006-11-10 Not applicable Colombia NECROTON CAPSULAS Orotic acid (150 mg) + Xanthine (75 mg) Capsule, coated Oral Laboratorios Incobra S.A. 2010-07-22 Not applicable Colombia ไลโปคอล Orotic acid (30 mg) + Ascorbic acid (30 mg) + Cyanocobalamin (0.001 mg) + Inositol (30 mg) + Nicotinamide (10 mg) + Pantothenic acid (5 mg) + Pyridoxine hydrochloride (1 mg) + Racemethionine (50 mg) + Riboflavin (1 mg) + Thiamine mononitrate (2 mg) + Thioctamide (3.5 mg) Tablet, sugar coated Oral บริษัท อินเตอร์ไทย ฟาร์มาซูติเคิ้ล แมนูแฟคเจอริ่ง จำกัด จำกัด 2005-05-13 Not applicable Thailand 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Pyrimidinecarboxylic acids
- Alternative Parents
- Hydropyrimidine carboxylic acids and derivatives / Pyrimidones / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds show 4 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Hydropyrimidine carboxylic acid derivative / Lactam / Monocarboxylic acid or derivatives show 10 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrimidinemonocarboxylic acid (CHEBI:16742)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 61H4T033E5
- CAS number
- 65-86-1
- InChI Key
- PXQPEWDEAKTCGB-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
- IUPAC Name
- 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
- SMILES
- OC(=O)C1=CC(=O)NC(=O)N1
References
- Synthesis Reference
Paul Rambacher, Siegfried Make, "Process for preparing orotic acid." U.S. Patent US4062847, issued November, 1960.
US4062847- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000226
- KEGG Drug
- D00055
- KEGG Compound
- C00295
- PubChem Compound
- 967
- PubChem Substance
- 46508903
- ChemSpider
- 942
- 7712
- ChEBI
- 16742
- ChEMBL
- CHEMBL1235017
- ZINC
- ZINC000001408068
- Therapeutic Targets Database
- DNC001065
- PDBe Ligand
- ORO
- Wikipedia
- Orotic_acid
- PDB Entries
- 1d3g / 1d3h / 1ep2 / 1f76 / 1j79 / 1jqv / 1jqx / 1jrb / 1jrc / 1lh0 … show 127 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Terminated Prevention Viral sepsis / Viruria 1 Not Available Completed Diagnostic Seasonal Allergic Rhinitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Intramuscular Injection Parenteral Injection, solution Intramuscular 12.5 mg Capsule, coated Oral Tablet, sugar coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 345.5 °C PhysProp water solubility 1820 mg/L (at 18 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.83 SANGSTER (1994) logS -1.93 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 4.51 mg/mL ALOGPS logP -0.89 ALOGPS logP -1.2 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 2.64 Chemaxon pKa (Strongest Basic) -6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 95.5 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 33.27 m3·mol-1 Chemaxon Polarizability 12.46 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5451 Blood Brain Barrier + 0.8092 Caco-2 permeable - 0.8368 P-glycoprotein substrate Non-substrate 0.7138 P-glycoprotein inhibitor I Non-inhibitor 0.9897 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.9671 CYP450 2C9 substrate Non-substrate 0.7072 CYP450 2D6 substrate Non-substrate 0.8144 CYP450 3A4 substrate Non-substrate 0.7887 CYP450 1A2 substrate Non-inhibitor 0.5857 CYP450 2C9 inhibitor Non-inhibitor 0.9709 CYP450 2D6 inhibitor Non-inhibitor 0.94 CYP450 2C19 inhibitor Non-inhibitor 0.9604 CYP450 3A4 inhibitor Non-inhibitor 0.9457 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 1.0 Ames test Non AMES toxic 0.9385 Carcinogenicity Non-carcinogens 0.9437 Biodegradation Ready biodegradable 0.8393 Rat acute toxicity 1.6077 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9864 hERG inhibition (predictor II) Non-inhibitor 0.979
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 132.7369941 predictedDarkChem Lite v0.1.0 [M-H]- 132.8475941 predictedDarkChem Lite v0.1.0 [M-H]- 132.8846941 predictedDarkChem Lite v0.1.0 [M-H]- 126.8485 predictedDeepCCS 1.0 (2019) [M+H]+ 133.8938941 predictedDarkChem Lite v0.1.0 [M+H]+ 133.6698941 predictedDarkChem Lite v0.1.0 [M+H]+ 133.8259941 predictedDarkChem Lite v0.1.0 [M+H]+ 130.01259 predictedDeepCCS 1.0 (2019) [M+Na]+ 133.6740941 predictedDarkChem Lite v0.1.0 [M+Na]+ 133.5234941 predictedDarkChem Lite v0.1.0 [M+Na]+ 133.4169941 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.95723 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
- Pharmacological action
- Unknown
- General Function
- Orotate phosphoribosyltransferase activity
- Specific Function
- Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to orotate, leading to the formation of orotidine monophosphate (OMP).
- Gene Name
- pyrE
- Uniprot ID
- P08870
- Uniprot Name
- Orotate phosphoribosyltransferase
- Molecular Weight
- 23561.74 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquinone binding
- Specific Function
- Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
- Gene Name
- DHODH
- Uniprot ID
- Q02127
- Uniprot Name
- Dihydroorotate dehydrogenase (quinone), mitochondrial
- Molecular Weight
- 42866.93 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Fmn binding
- Specific Function
- Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
- Gene Name
- pyrD
- Uniprot ID
- P0A7E1
- Uniprot Name
- Dihydroorotate dehydrogenase (quinone)
- Molecular Weight
- 36774.185 Da
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Not Available
- Gene Name
- pyrC
- Uniprot ID
- P05020
- Uniprot Name
- Dihydroorotase
- Molecular Weight
- 38827.045 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Lactococcus lactis subsp. cremoris
- Pharmacological action
- Unknown
- General Function
- Dihydroorotate dehydrogenase (fumarate) activity
- Specific Function
- Catalyzes the conversion of dihydroorotate to orotate with fumarate as the electron acceptor.
- Gene Name
- pyrDA
- Uniprot ID
- Q53ZE5
- Uniprot Name
- Dihydroorotate dehydrogenase A (fumarate)
- Molecular Weight
- 34209.99 Da
References
Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:06