Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H4N2O2 |
| Molecular Weight | 112.0868 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC=CC(=O)N1
InChI
InChIKey=ISAKRJDGNUQOIC-UHFFFAOYSA-N
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB03419 | https://www.drugs.com/international/uracil.html | https://www.ncbi.nlm.nih.gov/pubmed/28347333 | https://www.ncbi.nlm.nih.gov/pubmed/4053028
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB03419 | https://www.drugs.com/international/uracil.html | https://www.ncbi.nlm.nih.gov/pubmed/28347333 | https://www.ncbi.nlm.nih.gov/pubmed/4053028
Uracil is a common and naturally occurring pyrimidine derivative, one of the four nucleobases in the nucleic acid of RNA In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by it’s methylated form -- thymine. Originally discovered in 1900 by Alberto Ascoli, it was isolated by hydrolysis of yeast nuclein;[4] it was also found in bovine thymus and spleen, herring sperm, and wheat germ. It is a planar, unsaturated compound that has the ability to absorb light. Uracil readily undergoes regular reactions including oxidation, nitration, and alkylation. While in the presence of phenol (PhOH) and sodium hypochlorite (NaOCl), uracil can be visualized in ultraviolet light. Uracil also has the capability to react with elemental halogens because of the presence of more than one strongly electron donating group. Uracil readily undergoes addition to ribose sugars and phosphates to partake in synthesis and further reactions in the body. Uracil becomes uridine, uridine monophosphate (UMP), uridine diphosphate (UDP), uridine triphosphate (UTP), and uridine diphosphate glucose (UDP-glucose). Each one of these molecules is synthesized in the body and has specific functions. Uracil's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for reactions in the human body and in plants. Uracil can be used for drug delivery and as a pharmaceutical. When elemental fluorine is reacted with uracil, 5-fluorouracil is produced. 5-Fluorouracil is an anticancer drug (antimetabolite) used to masquerade as uracil during the nucleic acid replication process. In combination with Tegafur, uracil used as a chemotherapy drug (called UFT or UFUR) used in the treatment of cancer, primarily bowel cancer. UFT is an anticancer medication composed of a fixed molar ratio (1:4) of tegafur and uracil to be administered with calcium folinate.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3172 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Uftoral Approved UseINDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate |
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| Primary | Uftoral Approved UseINDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate |
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| Primary | Uftoral Approved UseINDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8612313/ |
350 mg/m² 1 times / day steady-state, oral dose: 350 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered: TEGAFUR |
URACIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
20.1 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8612313/ |
350 mg/m² 1 times / day steady-state, oral dose: 350 mg/m² route of administration: Oral experiment type: STEADY-STATE co-administered: TEGAFUR |
URACIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1000 mg/m2 single, oral Highest studied dose Dose: 1000 mg/m2 Route: oral Route: single Dose: 1000 mg/m2 Sources: |
healthy, 38 ± 9 years Health Status: healthy Age Group: 38 ± 9 years Sex: M+F Sources: |
|
248.4 mg/m2 1 times / day steady, oral RP2D Dose: 248.4 mg/m2, 1 times / day Route: oral Route: steady Dose: 248.4 mg/m2, 1 times / day Sources: |
unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: M+F Sources: |
Other AEs: Fatigue, Nausea... Other AEs: Fatigue (grade 1-2, 3 patients) Sources: Nausea (grade 1-2, 2 patients) |
552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Sources: |
unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: |
Other AEs: Granulocytopenia, Nausea... Other AEs: Granulocytopenia (grade 4, 1 patient) Sources: Nausea (grade 3, 1 patient) Thrombocytopenia (grade 3, 1 patient) Vomiting (grade 1-2, 5 patients) Fatigue (grade 1-2, 4 patients) Diarrhoea (grade 1-2, 4 patients) |
310.5 mg/m2 1 times / day steady, oral Highest studied dose Dose: 310.5 mg/m2, 1 times / day Route: oral Route: steady Dose: 310.5 mg/m2, 1 times / day Sources: |
unhealthy |
DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3-4, 3 patients) Sources: |
621 mg/m2 1 times / day steady, oral Highest studied dose Dose: 621 mg/m2, 1 times / day Route: oral Route: steady Dose: 621 mg/m2, 1 times / day Sources: |
unhealthy |
DLT: Granulocytopenia... Dose limiting toxicities: Granulocytopenia (grade 4, 4 patients) Sources: |
276 mg/m2 1 times / day steady, oral Dose: 276 mg/m2, 1 times / day Route: oral Route: steady Dose: 276 mg/m2, 1 times / day Sources: |
unhealthy |
DLT: Diarrhea... Dose limiting toxicities: Diarrhea (grade 3-4, 3 patients) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nausea | grade 1-2, 2 patients | 248.4 mg/m2 1 times / day steady, oral RP2D Dose: 248.4 mg/m2, 1 times / day Route: oral Route: steady Dose: 248.4 mg/m2, 1 times / day Sources: |
unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: M+F Sources: |
| Fatigue | grade 1-2, 3 patients | 248.4 mg/m2 1 times / day steady, oral RP2D Dose: 248.4 mg/m2, 1 times / day Route: oral Route: steady Dose: 248.4 mg/m2, 1 times / day Sources: |
unhealthy, 54 years Health Status: unhealthy Age Group: 54 years Sex: M+F Sources: |
| Diarrhoea | grade 1-2, 4 patients | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Sources: |
unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: |
| Fatigue | grade 1-2, 4 patients | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Sources: |
unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: |
| Vomiting | grade 1-2, 5 patients | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Sources: |
unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: |
| Nausea | grade 3, 1 patient | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Sources: |
unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: |
| Thrombocytopenia | grade 3, 1 patient | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Sources: |
unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: |
| Granulocytopenia | grade 4, 1 patient | 552 mg/m2 1 times / day steady, oral RP2D Dose: 552 mg/m2, 1 times / day Route: oral Route: steady Dose: 552 mg/m2, 1 times / day Sources: |
unhealthy, 59 years Health Status: unhealthy Age Group: 59 years Sex: M+F Sources: |
| Diarrhea | grade 3-4, 3 patients DLT |
310.5 mg/m2 1 times / day steady, oral Highest studied dose Dose: 310.5 mg/m2, 1 times / day Route: oral Route: steady Dose: 310.5 mg/m2, 1 times / day Sources: |
unhealthy |
| Granulocytopenia | grade 4, 4 patients DLT |
621 mg/m2 1 times / day steady, oral Highest studied dose Dose: 621 mg/m2, 1 times / day Route: oral Route: steady Dose: 621 mg/m2, 1 times / day Sources: |
unhealthy |
| Diarrhea | grade 3-4, 3 patients DLT |
276 mg/m2 1 times / day steady, oral Dose: 276 mg/m2, 1 times / day Route: oral Route: steady Dose: 276 mg/m2, 1 times / day Sources: |
unhealthy |
PubMed
| Title | Date | PubMed |
|---|---|---|
| First report of the cyanobacterial toxin cylindrospermopsin in New Zealand. | 2001-08 |
|
| Isolation and characterization of a U-specific 3'-5'-exonuclease from mitochondria of Leishmania tarentolae. | 2001-06-15 |
|
| Chimeras between single-stranded DNA-binding proteins from Escherichia coli and Mycobacterium tuberculosis reveal that their C-terminal domains interact with uracil DNA glycosylases. | 2001-05-18 |
|
| The role of leucine 191 of Escherichia coli uracil DNA glycosylase in the formation of a highly stable complex with the substrate mimic, ugi, and in uracil excision from the synthetic substrates. | 2001-05-18 |
|
| Functionally different AU- and G-rich cis-elements confer developmentally regulated mRNA stability in Trypanosoma cruzi by interaction with specific RNA-binding proteins. | 2001-05-11 |
|
| Oxidation of thymine to 5-formyluracil in DNA promotes misincorporation of dGMP and subsequent elongation of a mismatched primer terminus by DNA polymerase. | 2001-05-11 |
|
| Validity of an ELISA for N-acetyltransferase-2 (NAT2) phenotyping. | 2001-05-01 |
|
| Structural determinants of adenophostin A activity at inositol trisphosphate receptors. | 2001-05 |
|
| Role of MED1 (MBD4) Gene in DNA repair and human cancer. | 2001-05 |
|
| A possible role of Ku in mediating sequential repair of closely opposed lesions. | 2001-04-20 |
|
| The role of folic acid and Vitamin B12 in genomic stability of human cells. | 2001-04-18 |
|
| DNA damage from micronutrient deficiencies is likely to be a major cause of cancer. | 2001-04-18 |
|
| Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazol. | 2001-04-17 |
|
| Preparation of oligodeoxynucleotides containing 5-(N-methylpiperazinyl) and 5-benzyloxymethyl uracils. | 2001-04-17 |
|
| DNA repair and aging in mouse liver: 8-oxodG glycosylase activity increase in mitochondrial but not in nuclear extracts. | 2001-04-15 |
|
| [New drugs for colorectal cancer: UFT]. | 2001-04-13 |
|
| Methylenetetrahydrofolate reductase polymorphism is associated with folate pool in gastrointestinal cancer tissue. | 2001-04-13 |
|
| Analysis of gene induction and arrest site transcription in yeast with mutations in the transcription elongation machinery. | 2001-04-13 |
|
| Why Ppr1p is a weak activator of transcription. | 2001-04-06 |
|
| N(1)-C(5')-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution. | 2001-04-06 |
|
| Characterization of the full length uracil-DNA glycosylase in the extreme thermophile Thermotoga maritima. | 2001-04-04 |
|
| Phase II study of oral eniluracil, 5-fluorouracil, and leucovorin in patients with advanced colorectal carcinoma. | 2001-04-01 |
|
| Acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil and mesitylene: formation of photocycloadducts and their characterization. | 2001-04 |
|
| Schedule dependency of antitumor activity in combination therapy with capecitabine/5'-deoxy-5-fluorouridine and docetaxel in breast cancer models. | 2001-04 |
|
| Tuber physiology and properties of starch from tubers of transgenic potato plants with altered plastidic adenylate transporter activity. | 2001-04 |
|
| [(35)S]GTPgammaS autoradiography reveals a wide distribution of G(i/o)-linked ADP receptors in the nervous system: close similarities with the platelet P2Y(ADP) receptor. | 2001-04 |
|
| Photocatalytic degradation of the cyanotoxin cylindrospermopsin, using titanium dioxide and UV irradiation. | 2001-04 |
|
| Low-energy (5-40 eV) electron-stimulated desorption of anions from physisorbed DNA bases. | 2001-04 |
|
| Postsurgical sequential methotrexate/5-FU and leucovorin on outpatient basis for advanced colorectal carcinoma. | 2001-03-28 |
|
| 5'-Deoxyribose phosphate lyase activity of human DNA polymerase iota in vitro. | 2001-03-16 |
|
| Identification and quantification of base and nucleoside markers in extracts of Ganoderma lucidum, Ganoderma japonicum and Ganoderma capsules by micellar electrokinetic chromatography. | 2001-03-09 |
|
| HuR, a RNA stability factor, is expressed in malignant brain tumors and binds to adenine- and uridine-rich elements within the 3' untranslated regions of cytokine and angiogenic factor mRNAs. | 2001-03-01 |
|
| [Long-term survival of hormone-refractory prostate cancer: a case report]. | 2001-03-01 |
|
| Future directions in adjuvant therapy for stage III colon carcinoma. | 2001-03 |
|
| Effect of food on the oral bioavailability of UFT and leucovorin in cancer patients. | 2001-03 |
|
| The significance of dihydropyrimidine dehydrogenase (DPD) activity in bladder cancer. | 2001-03 |
|
| [A case of advanced gastric cancer complicated with liver metastases responding remarkably to combined chemotherapy with 5-fluorouracil and low-dose cisplatin, with UFT and low-dose cisplatin for maintenance on an outpatient basis]. | 2001-03 |
|
| P2Y receptor-mediated inhibition of voltage-activated Ca(2+) currents in PC12 cells. | 2001-03 |
|
| Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin. | 2001-02-23 |
|
| 5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism. | 2001-02-03 |
|
| Caffeine metabolism before and after liver transplantation. | 2001-02 |
|
| Confounded cytosine! Tinkering and the evolution of DNA. | 2001-02 |
|
| Quantum-chemical analysis of C-H...O and C-H...N interactions in RNA base pairs--H-bond versus anti-H-bond pattern. | 2001-02 |
|
| The effect of UV irradiation on uracil thin layer measured by optical waveguide lightmode spectroscopy. | 2001-01 |
|
| Prospective and randomized comparison of combined androgen blockade versus combination with oral UFT as an initial treatment for prostate cancer. | 2001-01 |
|
| Applications of microarray technology in breast cancer research. | 2001 |
|
| The oral fluorinated pyrimidines. | 2001 |
|
| NRG1 is required for glucose repression of the SUC2 and GAL genes of Saccharomyces cerevisiae. | 2001 |
|
| Fungal virulence studies come of age. | 2001 |
|
| Recent advances in imaging endogenous or transferred gene expression utilizing radionuclide technologies in living subjects: applications to breast cancer. | 2001 |
Sample Use Guides
UFT (tegafur- uracil) is an anticancer medication composed of a fixed molar ratio (1:4) of tegafur and uracil to be administered with calcium folinate. The usual dose is 300 mg/m2/day tegafur-uracil 90 mg/day calcium folinate (30 mg/dose) administered in three divided doses (every 8 hours) orally one hour before or one hour after meals for 28 consecutive days.
Route of Administration:
Oral
A cultured line of human lymphoid cells (8866) was grown in suspension in modified Eagle's medium plus 10% (vol/vol) fetal calf serum. All experiments were carried out with 20-S0 ml of cells in logarithmic phase of growth (6-9 X 105 cells per ml). Cells were incubated with methotrexate (10 ,gM) plus hypoxanthine (25 jM) (serine and glycine were already present in the medium) for 4 hr, after which [5-3H]dUrd (15-20 Ci/mmol, 1 Ci = 3.7 X 1010 becquerels; Moravek, City of Industry, CA) was added at levels specified and incubation was continued for an additional 2 hr. Cultures not treated with methotrexate were labeled for 30 rmin (in the presence of hypoxanthine alone). Ura, when present, was added at 10 mM 10 min before [3H]dUrd.
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LOINC |
75152-9
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30485-7
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NCI_THESAURUS |
C789
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LOINC |
13819-8
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75128-9
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25140-5
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C917
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m11305
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1174
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D014498
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CHEMBL566
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DTXSID4021424
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1705753
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66-22-8
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10995
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17568
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DB03419
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SUB20762
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URACIL
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KK-14
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200-621-9
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3970
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56HH86ZVCT
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100000086536
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ACTIVE MOIETY
