cedazuridine   Click here for help

GtoPdb Ligand ID: 11101

Synonyms: (4R)-2'-deoxy-2',2'-difluoro-3,4,5,6-tetrahydrouridine | ASTX727 (cedazuridine + decitabine) | compound 7a [PMID: 24520856]
Approved drug
cedazuridine is an approved drug (FDA (2020))
Compound class: Synthetic organic
Comment: Cedazuridine is a tetrahydrouridine-derived, orally available synthetic nucleoside analogue that was developed by Astex Pharmaceuticals. It inhibits cytidine deaminase (CDA) and was designed to be used as a pharmacoenhancer of drugs that are subject to CDA-mediated breakdown, for example the cytidine analogue antineoplastic hypomethylating agent decitabine. This mechanism permits oral delivery of decitabine (by inhibiting decitabine degradation in the gut and liver). It also allows lower doses of decitabine to be used, which improves tolerability to this cancer drug, whose administration is associated with GI-toxicity.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 102.26
Molecular weight 268.09
XLogP -1.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES OC[C@H]1O[C@H](C([C@@H]1O)(F)F)N1CC[C@H](NC1=O)O
Isomeric SMILES OC[C@H]1O[C@H](C([C@@H]1O)(F)F)N1CC[C@H](NC1=O)O
InChI InChI=1S/C9H14F2N2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h4-7,14-16H,1-3H2,(H,12,17)/t4-,5-,6-,7-/m1/s1
InChI Key VUDZSIYXZUYWSC-DBRKOABJSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
IUPAC Name Click here for help
(4R)-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one
International Nonproprietary Names Click here for help
INN number INN
10741 cedazuridine
Synonyms Click here for help
(4R)-2'-deoxy-2',2'-difluoro-3,4,5,6-tetrahydrouridine | ASTX727 (cedazuridine + decitabine) | compound 7a [PMID: 24520856]
Database Links Click here for help
BindingDB Ligand 50007029
CAS Registry No. 1141397-80-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL3237547
DrugCentral Ligand 5402
GtoPdb PubChem SID 434122162
PubChem CID 25267009
Search Google for chemical match using the InChIKey VUDZSIYXZUYWSC-DBRKOABJSA-N
Search Google for chemicals with the same backbone VUDZSIYXZUYWSC
Search PubMed clinical trials cedazuridine
Search PubMed titles cedazuridine
Search PubMed titles/abstracts cedazuridine
UniChem Compound Search for chemical match using the InChIKey VUDZSIYXZUYWSC-DBRKOABJSA-N
UniChem Connectivity Search for chemical match using the InChIKey VUDZSIYXZUYWSC-DBRKOABJSA-N