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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

Molecular Formula C4H3ClN2O2
Molecular Weight 146.532
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
PubMed

PubMed

TitleDatePubMed
N(1)-C(5')-linked dimer hydrates of 5-substituted uracils produced by anodic oxidation in aqueous solution.
2001 Apr 6
An improved resazurin-based cytotoxicity assay for hepatic cells.
2002
Detection and quantification of 5-chlorocytosine in DNA by stable isotope dilution and gas chromatography/negative ion chemical ionization/mass spectrometry.
2002 Feb
5-Chlorouracil, a marker of DNA damage from hypochlorous acid during inflammation. A gas chromatography-mass spectrometry assay.
2003 Aug 29
Phase I study of irinotecan and S-1 combination therapy in patients with metastatic gastric cancer.
2003 Dec
Phagocytes produce 5-chlorouracil and 5-bromouracil, two mutagenic products of myeloperoxidase, in human inflammatory tissue.
2003 Jun 27
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 Aug 1
Influence of halogenation on the properties of uracil and its noncovalent interactions with alkali metal ions. Threshold collision-induced dissociation and theoretical studies.
2004 Dec 15
Electron attachment to chlorouracil: a comparison between 6-ClU and 5-ClU.
2004 Jan 8
Synthesis and evaluation of 6-methylene-bridged uracil derivatives. Part 1: discovery of novel orally active inhibitors of human thymidine phosphorylase.
2004 Jul 1
Measurement of drug release from microcarriers by microdialysis.
2005 Jul
Hydrophilic interaction liquid chromatography-APCI-mass spectrometry determination of 5-fluorouracil in plasma and tissues.
2005 Jul 15
Myeloperoxidase generates 5-chlorouracil in human atherosclerotic tissue: a potential pathway for somatic mutagenesis by macrophages.
2006 Feb 10
Controlled delivery of 5-chlorouracil using poly(ortho esters) in filtering surgery for glaucoma.
2008 Jul
Significance of 5-fluorouracil-related enzyme activities in predicting sensitivity to 5-fluorouracil in bladder carcinoma.
2009 Apr
Base pairing configuration and stability of an oligonucleotide duplex containing a 5-chlorouracil-adenine base pair.
2009 Aug 11
pH-Dependent configurations of a 5-chlorouracil-guanine base pair.
2009 Dec 1
Polymerase incorporation and miscoding properties of 5-chlorouracil.
2010 Apr 19
Paclitaxel inhibits growth, migration and collagen production of human Tenon's fibroblasts--potential use in drug-eluting glaucoma drainage devices.
2010 Feb
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:42:09 GMT 2023
Edited
by admin
on Sat Dec 16 00:42:09 GMT 2023
Record UNII
7LQ4V03RNY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
5-CHLOROURACIL
Systematic 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
FLUOROURACIL RELATED COMPOUND E
USP-RS  
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 Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
PUBCHEM
15758
Created by admin on Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
217-339-7
Created by admin on Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
RS_ITEM_NUM
1279054
Created by admin on Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
FDA UNII
7LQ4V03RNY
Created by admin on Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
CHEBI
60762
Created by admin on Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
NSC
28172
Created by admin on Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID7075137
Created by admin on Sat Dec 16 00:42:09 GMT 2023 , Edited by admin on Sat Dec 16 00:42:09 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
USP Peak Value = 0.15%
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP