U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H4N2O2
Molecular Weight 112.0869
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of URACIL

SMILES

c1cnc(nc1O)O

InChI

InChIKey=ISAKRJDGNUQOIC-UHFFFAOYSA-N
InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

HIDE SMILES / InChI

Molecular Formula C4H4N2O2
Molecular Weight 112.0869
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Uftoral

Approved Use

INDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate
Primary
Uftoral

Approved Use

INDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate
Primary
Uftoral

Approved Use

INDICATIONS. UFT is indicated for the first-line treatment of metastatic colorectal cancer with calcium folinate
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
20.3 μM
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

AUC

ValueDoseCo-administeredAnalytePopulation
20.1 μM × h
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

Doses

DosePopulationAdverse 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)
Nausea (grade 1-2, 2 patients)
Sources:
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)
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)
Sources:
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
Health Status: unhealthy
Sources:
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
Health Status: unhealthy
Sources:
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
Health Status: unhealthy
Sources:
DLT: Diarrhea...
Dose limiting toxicities:
Diarrhea (grade 3-4, 3 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Sources:
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
Health Status: unhealthy
Sources:
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
Health Status: unhealthy
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
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
UAG readthrough in mammalian cells: effect of upstream and downstream stop codon contexts reveal different signals.
2001
Acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil and mesitylene: formation of photocycloadducts and their characterization.
2001 Apr
Schedule dependency of antitumor activity in combination therapy with capecitabine/5'-deoxy-5-fluorouridine and docetaxel in breast cancer models.
2001 Apr
Tuber physiology and properties of starch from tubers of transgenic potato plants with altered plastidic adenylate transporter activity.
2001 Apr
[(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 Apr
Photocatalytic degradation of the cyanotoxin cylindrospermopsin, using titanium dioxide and UV irradiation.
2001 Apr
Low-energy (5-40 eV) electron-stimulated desorption of anions from physisorbed DNA bases.
2001 Apr
Phase II study of oral eniluracil, 5-fluorouracil, and leucovorin in patients with advanced colorectal carcinoma.
2001 Apr 1
DNA repair and aging in mouse liver: 8-oxodG glycosylase activity increase in mitochondrial but not in nuclear extracts.
2001 Apr 15
The role of folic acid and Vitamin B12 in genomic stability of human cells.
2001 Apr 18
DNA damage from micronutrient deficiencies is likely to be a major cause of cancer.
2001 Apr 18
A possible role of Ku in mediating sequential repair of closely opposed lesions.
2001 Apr 20
Why Ppr1p is a weak activator of transcription.
2001 Apr 6
N(1)-C(5')-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution.
2001 Apr 6
First report of the cyanobacterial toxin cylindrospermopsin in New Zealand.
2001 Aug
Caffeine metabolism before and after liver transplantation.
2001 Feb
[Complete response of a massive hepatocellular carcinoma with lung metastasis to UFT (DPD inhibitory fluoroprymidines: DIF)].
2001 Feb
[A case of gastric cancer with liver metastases successfully treated with combination therapy of systemic and hepatic arterial infusion chemotherapy].
2001 Feb
[Study on the intensity of MMC and UFT in postoperative adjuvant chemotherapy for gastric cancer--study report of JFMTC Study No. 10].
2001 Feb
UFT plus oral leucovorin calcium (Orzel) and radiation in combined modality therapy: a comprehensive review.
2001 Feb 20
Synthesis of analogues of the O-beta-D-ribofuranosyl nucleoside moiety of liposidomycins. Part 1: contribution of the amino group and the uracil moiety upon the inhibition of MraY.
2001 Feb 26
In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents.
2001 Feb 26
5-Formyluracil and its nucleoside derivatives confer toxicity and mutagenicity to mammalian cells by interfering with normal RNA and DNA metabolism.
2001 Feb 3
The effect of UV irradiation on uracil thin layer measured by optical waveguide lightmode spectroscopy.
2001 Jan
Prospective and randomized comparison of combined androgen blockade versus combination with oral UFT as an initial treatment for prostate cancer.
2001 Jan
Synthesis, characterisation, X-ray structure and biological activity of three new 5-formyluracil thiosemicarbazone complexes.
2001 Jan 15
Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazol.
2001 Jan-Feb
Preparation of oligodeoxynucleotides containing 5-(N-methylpiperazinyl) and 5-benzyloxymethyl uracils.
2001 Jan-Feb
[New drugs for colorectal cancer: UFT].
2001 Jan-Feb
Methylenetetrahydrofolate reductase polymorphism is associated with folate pool in gastrointestinal cancer tissue.
2001 Jan-Feb
Postsurgical sequential methotrexate/5-FU and leucovorin on outpatient basis for advanced colorectal carcinoma.
2001 Jan-Feb
Isolation and characterization of a U-specific 3'-5'-exonuclease from mitochondria of Leishmania tarentolae.
2001 Jun 15
Future directions in adjuvant therapy for stage III colon carcinoma.
2001 Mar
Effect of food on the oral bioavailability of UFT and leucovorin in cancer patients.
2001 Mar
The significance of dihydropyrimidine dehydrogenase (DPD) activity in bladder cancer.
2001 Mar
[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 Mar
P2Y receptor-mediated inhibition of voltage-activated Ca(2+) currents in PC12 cells.
2001 Mar
Recent progress in the biology, chemistry and structural biology of DNA glycosylases.
2001 Mar
Identification and quantification of base and nucleoside markers in extracts of Ganoderma lucidum, Ganoderma japonicum and Ganoderma capsules by micellar electrokinetic chromatography.
2001 Mar 9
Structural determinants of adenophostin A activity at inositol trisphosphate receptors.
2001 May
Role of MED1 (MBD4) Gene in DNA repair and human cancer.
2001 May
Validity of an ELISA for N-acetyltransferase-2 (NAT2) phenotyping.
2001 May 1
Functionally different AU- and G-rich cis-elements confer developmentally regulated mRNA stability in Trypanosoma cruzi by interaction with specific RNA-binding proteins.
2001 May 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 May 11
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 May 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 May 18
Patents

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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:54:36 UTC 2021
Edited
by admin
on Sat Jun 26 10:54:36 UTC 2021
Record UNII
56HH86ZVCT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
URACIL
INCI   JAN   MART.   MI   USAN   USP-RS   WHO-DD  
USAN   INCI  
Official Name English
PYRIMIDINE-2,4(1H,3H)-DIONE
Systematic Name English
NSC-3970
Code English
2,4(1H,3H)-PYRIMIDINEDIONE
Systematic Name English
URACIL [USAN]
Common Name English
LAMIVUDINE IMPURITY E RS [USP]
Common Name English
SQ-7726
Code English
URACIL [MART.]
Common Name English
SQ-8493
Code English
PYROD
Common Name English
LAMIVUDINE IMPURITY F [EP]
Common Name English
URACIL [JAN]
Common Name English
SQ-6201
Code English
LAMIVUDINE IMPURITY E [USP]
Common Name English
URACIL [MI]
Common Name English
BMS-205603-01
Code English
FLUOROURACIL SPECIFIED COMPOUND C [USP]
Common Name English
URACIL [USP-RS]
Common Name English
URACIL [WHO-DD]
Common Name English
HYBAR X
Common Name English
FLUOROURACIL IMPURITY C [EP]
Common Name English
URACIL [INCI]
Common Name English
Classification Tree Code System Code
LOINC 75152-9
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
LOINC 30485-7
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
NCI_THESAURUS C789
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
LOINC 13819-8
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
LOINC 75128-9
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
LOINC 25140-5
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C917
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
MERCK INDEX
M11305
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY Merck Index
PUBCHEM
1174
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
MESH
D014498
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL566
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
EPA CompTox
66-22-8
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
USP_CATALOG
1705753
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY USP-RS
CAS
66-22-8
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
RXCUI
10995
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB03419
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
EVMPD
SUB20762
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
WIKIPEDIA
URACIL
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-621-9
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
FDA UNII
56HH86ZVCT
Created by admin on Sat Jun 26 10:54:37 UTC 2021 , Edited by admin on Sat Jun 26 10:54:37 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY