Sapacitabine
N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide
Molecular Identity
Sapacitabine
N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide
PubChem CID: 153970
Sapacitabine is a nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical development for the treatment of acute myeloid leukemia (AML). It has a role as an antimetabolite, an antineoplastic agent, a prodrug and a DNA synthesis inhibitor. It is a secondary carboxamide, a nitrile and a nucleoside analogue. It is functionally related to a CNDAC and a hexadecanoic acid.
2D Structure
Properties
C26H42N4O5
Molecular Formula
490.60
Molecular Weight
g/mol
490.3155
Exact Mass
Da
5.2
XLogP
Above Lipinski threshold
135
TPSA
Good oral absorption (< 140 A²)
3
H-Bond Donors
6
H-Bond Acceptors
775
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Sapacitabine151823-14-2CS-682CYC682sapacitabinaCYC-682CS682CS 682sapacitabinumCYC 682W335P73C3LN-(1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl)hexadecanamideCHEBI:145429DTXSID90164887Hexadecanamide, N-(1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl)-
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Sapacitabine
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