| 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)
| Molecular Formula | C4H4N2O2 |
| Molecular Weight | 112.0868 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
Doses
AEs
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
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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