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Cedazuridine

CAT: 0127-BUP07818-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0127-BUP07818-01Size:1 mg
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CAS Number
1141397-80-9
Synonyms
(4R) -2'-Deoxy-2',2'-difluoro-3,4,5,6-tetrahydrouridine
Purity
=98%
Smiles
OC[C@H]1O[C@@H](N2CC[C@@H](O)NC2=O)C(F)(F)[C@@H]1O

Chemical Information

Cedazuridine

Myelodysplastic syndromes (MDS) are a group of hematopoietic neoplasms that give rise to variable cytopenias progressing to secondary acute myeloid leukemia (sAML), which is invariably fatal if untreated. Hypomethylating agents such as [decitabine] and [azacitidine] are used to treat MDS through inducing DNA hypomethylation and apoptosis of cancerous cells. Although effective, these compounds are rapidly metabolized by cytidine deaminase (CDA) prior to reaching systemic circulation when administered orally, necessitating intramuscular or intravenous administration routes. Cedazuridine is a fluorinated tetrahydrouridine derivative specifically designed to inhibit CDA and facilitate oral administration of hypomethylating agents. Cedazuridine was first reported in 2014, and was subsequently approved by the FDA on July 7, 2020, in combination with [decitabine] for sale by Astex Pharmaceuticals Inc under the name INQOVI®.

CAS Number1141397-80-9
PubChem CID25267009
IUPAC Name(4R)-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one
Molecular FormulaC9H14F2N2O5
Molecular Weight268.21
XLogP-1.1
Topological Polar Surface Area102
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count18
Formal Charge0
Complexity343
SMILES
C1CN(C(=O)N[C@@H]1O)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
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
InChIKey
VUDZSIYXZUYWSC-DBRKOABJSA-N
Chemical Structure
2D Structure
2D structure of Cedazuridine
CAS: 1141397-80-9
CID: 25267009
Formula: C9H14F2N2O5
MW: 268.21
Interactive 3D Structure
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View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight268.21
XLogP3-1.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass268.08707788
Monoisotopic Mass268.08707788
Topological Polar Surface Area102 Ų
Heavy Atom Count18
Formal Charge0
Complexity343
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
MBS5776695Cedazuridine
T60708-01Cedazuridine hydrochloride
HY-109081R-01Cedazuridine (Standard)
HY-109081ACedazuridine (hydrochloride)
RM-C582005-01Cedazuridine Impurity 5
RM-C582003-01Cedazuridine Impurity 3
RM-C582001-01Cedazuridine Impurity 1
RM-C582004-01Cedazuridine Impurity 4
RM-C582002-01Cedazuridine Impurity 2

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