Identification
- Summary
Uracil is an antineoplastic agent used in combination with tegafur to treat various cancers, including breast, prostate, and liver cancer.
- Generic Name
- Uracil
- DrugBank Accession Number
- DB03419
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Uracil (DB03419)
- Weight
- Average: 112.0868
Monoisotopic: 112.027277382 - Chemical Formula
- C4H4N2O2
- Synonyms
- Uracil
- External IDs
- BMS-205603-01
- NSC-3970
- SQ-6201
Pharmacology
- Indication
Not Available
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism URibosomal small subunit pseudouridine synthase A Not Available Escherichia coli (strain K12) UUracil-DNA glycosylase Not Available HHV-1 UUracil-DNA glycosylase Not Available Escherichia coli O157:H7 UDihydropyrimidine dehydrogenase [NADP(+)] Not Available Humans UUridine-cytidine kinase-like 1 Not Available Humans UUracil-DNA glycosylase Not Available Thermus thermophilus UPyrimidine-nucleoside phosphorylase Not Available Geobacillus stearothermophilus - 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.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Carnosinuria, Carnosinemia Disease Pyrimidine Metabolism Metabolic MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy) Disease beta-Alanine Metabolism Metabolic beta-Ureidopropionase Deficiency Disease Dihydropyrimidinase Deficiency Disease UMP Synthase Deficiency (Orotic Aciduria) Disease GABA-Transaminase Deficiency Disease Ureidopropionase Deficiency Disease - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Uracil is combined with Acenocoumarol. Cimetidine The serum concentration of Uracil can be increased when it is combined with Cimetidine. Dicoumarol The risk or severity of bleeding can be increased when Uracil is combined with Dicoumarol. Fluindione The risk or severity of bleeding can be increased when Uracil is combined with Fluindione. Folic acid The risk or severity of adverse effects can be increased when Folic acid is combined with Uracil. Fosphenytoin The serum concentration of Fosphenytoin can be increased when it is combined with Uracil. Gemcitabine The serum concentration of Uracil can be increased when it is combined with Gemcitabine. Gimeracil The serum concentration of Uracil can be increased when it is combined with Gimeracil. Leucovorin The risk or severity of adverse effects can be increased when Leucovorin is combined with Uracil. Levoleucovorin The risk or severity of adverse effects can be increased when Levoleucovorin is combined with Uracil. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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 UFT CAPSULE Uracil (224 mg) + Tegafur (100 mg) Capsule Oral PHARMAFORTE SINGAPORE PTE LTD 1989-09-22 Not applicable Singapore ยูนิโทรอล แคปส์ Uracil (224 MG) + Tegafur (100 MG) Capsule Oral บริษัท เคนยากุ (ประเทศไทย) จำกัด 2012-01-18 Not applicable Thailand 
ยูเฟอร์ Uracil (224 MG) + Tegafur (100 MG) Capsule Oral บริษัท อเมริกัน ไต้หวัน ไบโอฟาร์ม จำกัด 2001-08-01 Not applicable Thailand
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Pyrimidones
- Alternative Parents
- Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound show 5 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrimidone, pyrimidine nucleobase (CHEBI:17568) / pyrimidines (C00106) / a pyrimidine-related compound, a pyrimidine base (URACIL)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 56HH86ZVCT
- CAS number
- 66-22-8
- InChI Key
- ISAKRJDGNUQOIC-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
- IUPAC Name
- 1,2,3,4-tetrahydropyrimidine-2,4-dione
- SMILES
- O=C1NC=CC(=O)N1
References
- Synthesis Reference
Kurt Klemm, Wolfgang Schoetensack, Wolfgang Prusse, "Aryl-substituted piperazinyl-alkylamino-uracils, -uracil ethers and -uracil thioethers and method for their production." U.S. Patent US3957786, issued September, 1951.
US3957786- General References
- Not Available
- External Links
- PDB Entries
- 1bd4 / 1brw / 1emj / 1flz / 1gth / 1jls / 1ksk / 1ksl / 1oe5 / 1q3f … show 50 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 100 mg Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 338 °C PhysProp water solubility 3600 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -1.07 HANSCH,C ET AL. (1995) logS -1.48 ADME Research, USCD Caco2 permeability -5.37 ADME Research, USCD pKa 9.45 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 26.5 mg/mL ALOGPS logP -1.2 ALOGPS logP -0.86 ChemAxon logS -0.63 ALOGPS pKa (Strongest Acidic) 9.77 ChemAxon pKa (Strongest Basic) -5.5 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 58.2 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 25.97 m3·mol-1 ChemAxon Polarizability 9.37 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 + 0.9591 Blood Brain Barrier + 0.9907 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.785 P-glycoprotein inhibitor I Non-inhibitor 0.9543 P-glycoprotein inhibitor II Non-inhibitor 0.9968 Renal organic cation transporter Non-inhibitor 0.9073 CYP450 2C9 substrate Non-substrate 0.7561 CYP450 2D6 substrate Non-substrate 0.8331 CYP450 3A4 substrate Non-substrate 0.793 CYP450 1A2 substrate Non-inhibitor 0.7271 CYP450 2C9 inhibitor Non-inhibitor 0.9713 CYP450 2D6 inhibitor Non-inhibitor 0.9719 CYP450 2C19 inhibitor Non-inhibitor 0.981 CYP450 3A4 inhibitor Non-inhibitor 0.9707 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.993 Ames test Non AMES toxic 0.9178 Carcinogenicity Non-carcinogens 0.9471 Biodegradation Ready biodegradable 0.7648 Rat acute toxicity 1.2228 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9614 hERG inhibition (predictor II) Non-inhibitor 0.968
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Rna binding
- Specific Function
- Responsible for synthesis of pseudouridine from uracil-516 in 16S ribosomal RNA.
- Gene Name
- rsuA
- Uniprot ID
- P0AA43
- Uniprot Name
- Ribosomal small subunit pseudouridine synthase A
- Molecular Weight
- 25865.12 Da
References
- Kind
- Protein
- Organism
- HHV-1
- Pharmacological action
- Unknown
- General Function
- Uracil dna n-glycosylase activity
- Specific Function
- Excises uracil residues from the DNA which can arise as a result of misincorporation of dUMP residues by DNA polymerase or deamination of cytosine. Therefore may reduce deleterious uracil incorpora...
- Gene Name
- Not Available
- Uniprot ID
- P10186
- Uniprot Name
- Uracil-DNA glycosylase
- Molecular Weight
- 36327.865 Da
References
- Kind
- Protein
- Organism
- Escherichia coli O157:H7
- Pharmacological action
- Unknown
- General Function
- Uracil dna n-glycosylase activity
- Specific Function
- Excises uracil residues from the DNA which can arise as a result of misincorporation of dUMP residues by DNA polymerase or due to deamination of cytosine.
- Gene Name
- ung
- Uniprot ID
- Q8X444
- Uniprot Name
- Uracil-DNA glycosylase
- Molecular Weight
- 25662.02 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein homodimerization activity
- Specific Function
- Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
- Gene Name
- DPYD
- Uniprot ID
- Q12882
- Uniprot Name
- Dihydropyrimidine dehydrogenase [NADP(+)]
- Molecular Weight
- 111400.32 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
- Humans
- Pharmacological action
- Unknown
- General Function
- Uridine kinase activity
- Specific Function
- May contribute to UTP accumulation needed for blast transformation and proliferation.
- Gene Name
- UCKL1
- Uniprot ID
- Q9NWZ5
- Uniprot Name
- Uridine-cytidine kinase-like 1
- Molecular Weight
- 61140.395 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
- Thermus thermophilus
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- Not Available
- Gene Name
- udg
- Uniprot ID
- Q5SKC5
- Uniprot Name
- Uracil-DNA glycosylase
- Molecular Weight
- 22965.68 Da
- Kind
- Protein
- Organism
- Geobacillus stearothermophilus
- Pharmacological action
- Unknown
- General Function
- Pyrimidine-nucleoside phosphorylase activity
- Specific Function
- Catalyzes phosphorolysis of the pyrimidine nucleosides uridine, thymidine and 2'-deoxyuridine with the formation of the corresponding pyrimidine base and ribose-1-phosphate.
- Gene Name
- pdp
- Uniprot ID
- P77836
- Uniprot Name
- Pyrimidine-nucleoside phosphorylase
- Molecular Weight
- 46331.92 Da
Drug created at June 13, 2005 13:24 / Updated at June 08, 2021 11:32