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151823-14-2

151823-14-2 Structure

151823-14-2 Structure
IdentificationBack Directory
[Name]

Sapacitabine
[CAS]

151823-14-2
[Synonyms]

CNDAC
CS-682
CS-2513
CYC 682
Sapacitabine
10G, 50G, 100G, 1KG
Sapacitabine (CYC682)
CYC 682; CYC-682; CS-682; CS682; CS 682
1-(2-Deoxy-2-cyano-β-D-arabinofuranosyl)cytosine
1-(2-C-Cyano-2-deoxy-β-D-arabino-pentofuranosyl)cytosine
2'-cyano-2'-deoxy-N4-palMitoyl-1-β-D-arabinofuranosyl-cytosine, sapacitabine, CYC682
4-Amino-1-[(3β-cyano-4α-hydroxy-5β-hydroxymethyltetrahydrofuran)-2β-yl]pyrimidin-2(1H)-one
1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-4-(palMitoylaMino)pyriMidin-2(1H)-one,Sapacitabine
Hexadecanamide, N-[1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]-
N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2- oxo-pyrimidin-4-yl]hexadecanamide
[Molecular Formula]

C26H42N4O5
[MDL Number]

MFCD00919466
[MOL File]

151823-14-2.mol
[Molecular Weight]

490.64
Chemical PropertiesBack Directory
[Melting point ]

>177°C (dec.)
[density ]

1.21±0.1 g/cm3(Predicted)
[storage temp. ]

-20°C Freezer, Under inert atmosphere
[solubility ]

DMSO (Slightly), Methanol (Slightly, Heated)
[form ]

Solid
[pka]

10.04±0.20(Predicted)
[color ]

White to Off-White
[InChIKey]

LBGFKUUHOPIEMA-PEARBKPGSA-N
[SMILES]

N1\C(=N\C(=O)CCCCCCCCCCCCCCC)\C=CN(C1=O)[C@@H]2O[C@@H]([C@H]([C@@H]2C#N)O)CO
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

Sapacitabine, it is an orally available nucleoside analog prodrug of CNDAC that acts through a dual mechanism. It has potential use in chemotherapy.
[Definition]

ChEBI: 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 nucleoside analogue, a nitrile and a secondary carboxamide. It is functionally related to a hexadecanoic acid and a CNDAC.
[Biochem/physiol Actions]

Sapacitabine is an orally active prodrug of nucleoside analog CNDAC that exhibits potent anti-tumor activity in both blood and solid tumors. CNDAC incorporates into DNA where it causes single-strand breaks (SSBs), which are converted into double strand breaks (DSBs) during S phase.
[in vivo]

On Day 14, the Sapacitabine (5?mg/kg)+vorinostat (33?mg/kg) group has a mean tumour volume of 245?mm3 and a tumour growth inhibition (TGI) of 92%, whereas the Sapacitabine (15?mg/kg)+vorinostat (33 mg/kg) group has a mean tumour volume of 107?mm3 and a TGI of 112%[2].

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