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.
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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
IUPAC Name Click here for help
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
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