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Details

Stereochemistry ACHIRAL
Molecular Formula C4H3ClN2O2
Molecular Weight 146.532
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5-CHLOROURACIL

SMILES

ClC1=CNC(=O)NC1=O

InChI

InChIKey=ZFTBZKVVGZNMJR-UHFFFAOYSA-N
InChI=1S/C4H3ClN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)

HIDE SMILES / InChI

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
PubMed

PubMed

TitleDatePubMed
Characterization of a novel lymph node metastasis model from human colonic cancer and its preclinical use for comparison of anti-metastatic efficacy between oral S-1 and UFT/ LV.
2010-08
Polymerase incorporation and miscoding properties of 5-chlorouracil.
2010-04-19
A new, validated HPLC-MS/MS method for the simultaneous determination of the anti-cancer agent capecitabine and its metabolites: 5'-deoxy-5-fluorocytidine, 5'-deoxy-5-fluorouridine, 5-fluorouracil and 5-fluorodihydrouracil, in human plasma.
2010-04
Paclitaxel inhibits growth, migration and collagen production of human Tenon's fibroblasts--potential use in drug-eluting glaucoma drainage devices.
2010-02
Comparative study of HOCl-inflicted damage to bacterial DNA ex vivo and within cells.
2010-01-15
[Markers of chloric acid (I) in biological systems--identification and properties].
2010
pH-Dependent configurations of a 5-chlorouracil-guanine base pair.
2009-12-01
Reactive oxygen and nitrogen species induce protein and DNA modifications driving arthrofibrosis following total knee arthroplasty.
2009-11-13
Base pairing configuration and stability of an oligonucleotide duplex containing a 5-chlorouracil-adenine base pair.
2009-08-11
Retrospective analysis of S-1 monotherapy in patients with metastatic colorectal cancer after failure to fluoropyrimidine and irinotecan or to fluoropyrimidine, irinotecan and oxaliplatin.
2009-05
Significance of 5-fluorouracil-related enzyme activities in predicting sensitivity to 5-fluorouracil in bladder carcinoma.
2009-04
Controlled delivery of 5-chlorouracil using poly(ortho esters) in filtering surgery for glaucoma.
2008-07
Examination of hypochlorous acid-induced damage to cytosine residues in a CpG dinucleotide in DNA.
2008-06
[Clinical benefit of S-1 in metastatic breast cancer].
2006-06
Myeloperoxidase generates 5-chlorouracil in human atherosclerotic tissue: a potential pathway for somatic mutagenesis by macrophages.
2006-02-10
Evaluation of novel one-electron reduction with metal in DNA.
2006
Hydrophilic interaction liquid chromatography-APCI-mass spectrometry determination of 5-fluorouracil in plasma and tissues.
2005-07-15
Measurement of drug release from microcarriers by microdialysis.
2005-07
Influence of halogenation on the properties of uracil and its noncovalent interactions with alkali metal ions. Threshold collision-induced dissociation and theoretical studies.
2004-12-15
Thymidylate synthase predictive power is overcome by irinotecan combination therapy with S-1 for gastric cancer.
2004-10-04
Synthesis and characterization of oligonucleotides containing 5-chlorocytosine.
2004-09
Phase I and pharmacokinetic study of the oral fluoropyrimidine S-1 on a once-daily-for-28-day schedule in patients with advanced malignancies.
2004-08-01
Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 1: discovery of novel orally active inhibitors of human thymidine phosphorylase.
2004-07-01
Alternate-day oral therapy with TS-1 for advanced gastric cancer.
2004-06
Electron attachment to chlorouracil: a comparison between 6-ClU and 5-ClU.
2004-01-08
Phase I study of irinotecan and S-1 combination therapy in patients with metastatic gastric cancer.
2003-12
5-Chlorouracil, a marker of DNA damage from hypochlorous acid during inflammation. A gas chromatography-mass spectrometry assay.
2003-08-29
Phagocytes produce 5-chlorouracil and 5-bromouracil, two mutagenic products of myeloperoxidase, in human inflammatory tissue.
2003-06-27
Analytical and pharmacokinetic studies with 5-chloro-2'-deoxycytidine.
2002-11-15
Loss of oxidized and chlorinated bases in DNA treated with reactive oxygen species: implications for assessment of oxidative damage in vivo.
2002-08-30
Detection and quantification of 5-chlorocytosine in DNA by stable isotope dilution and gas chromatography/negative ion chemical ionization/mass spectrometry.
2002-02
An improved resazurin-based cytotoxicity assay for hepatic cells.
2002
Synthesis of 5-chloro-1-(2,3-dideoxy-3-fluoro-beta-D-glycero-hex-2- enopyranose-4-ulosyl)uracil as potential anticancer/antiviral agent.
2001-09-21
N(1)-C(5')-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution.
2001-04-06
Simultaneous determination of flucytosine and fluorouracil in human plasma by high-performance liquid chromatography.
2001-04
Determination of 5-fluorouracil in environmental samples by solid-phase extraction and high-performance liquid chromatography with ultraviolet detection.
2001-01-05
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.
1994-08-17
Interaction of monoclonal antibodies directed against bromodeoxyuridine with pyrimidine bases, nucleosides, and DNA.
1986-03-01
Name Type Language
5-CHLOROURACIL
Systematic Name English
FLUOROURACIL RELATED COMPOUND E
USP-RS  
Preferred Name English
5-CHLORO-2,4-DIHYDROXYPYRIMIDINE
Systematic Name English
FLUOROURACIL RELATED COMPOUND E [USP-RS]
Common Name English
5-CHLOROPYRIMIDINE-2,4(1H,3H)-DIONE
Systematic Name English
CHLOROURACIL, 5-
Systematic Name English
FLUOROURACIL IMPURITY E [EP IMPURITY]
Common Name English
FLUOROURACIL RELATED COMPOUND E [USP IMPURITY]
Common Name English
NSC-28172
Code English
5-CHLORO-2,4-PYRIMIDINEDIONE
Systematic Name English
2,4(1H,3H)-PYRIMIDINEDIONE, 5-CHLORO-
Systematic Name English
Code System Code Type Description
CAS
1820-81-1
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY
PUBCHEM
15758
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-339-7
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY
RS_ITEM_NUM
1279054
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY
FDA UNII
7LQ4V03RNY
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY
CHEBI
60762
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY
NSC
28172
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID7075137
Created by admin on Mon Mar 31 20:39:23 GMT 2025 , Edited by admin on Mon Mar 31 20:39:23 GMT 2025
PRIMARY