Compound: Sapacitabine
SMILES: O=c1nc(NC(=O)CCCCCCCCCCCCCCC)ccn1[C@@H]2O[C@H](CO)[C@H]([C@@H]2C#N)O
InChIKey: LBGFKUUHOPIEMA-PEARBKPGSA-N
Synonyms: Sapacitabine, 151823-14-2, CS-682, CYC682, sapacitabina, CYC-682, CS682, CS 682, sapacitabinum, CYC 682, W335P73C3L, N-(1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl)hexadecanamide, CHEBI:145429, DTXSID90164887, Hexadecanamide, N-(1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl)-, 2'-C-cyano-2'-deoxy-1-arabinofuranosyl-N(4)-palmitoylcytosine, N-[1-(2-Cyano-2-deoxy-beta-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]hexadecanamide, CNDAC cpd, RefChem:931256, DTXCID9087378, N-(1-((2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)hexadecanamide, N-(1-(2-Cyano-2-deoxy-beta-D-arabinofuranosyl)-2-oxo-1,2-dihydropyrimidin-4-yl)-hexadecanamide, N-(1-((2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)palmitamide, N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide, PCNDAC, Sapacitabine [USAN:INN], CS682;CYC682, UNII-W335P73C3L, N-[1-(2-Cyano-2-deoxy-ss-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]hexadecanamide; CS 682; CS 682, MFCD00919466, Sapacitabine (USAN/INN), SAPACITABINE [INN], SAPACITABINE [USAN], Sapacitabine (CYC682)?, SAPACITABINE [MART.], SAPACITABINE [WHO-DD], SCHEMBL711854, orb1679012, CHEMBL2105681, LBGFKUUHOPIEMA-PEARBKPGSA-N, GLXC-10703, EX-A1617, NSC791785, DB06365, NSC-791785, AC-36130, HY-16445, MS-29120, N-[1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-2-oxo-1,2-dihydropyrimidine-4-yl]hexadecanamide, CS-0006340, NS00071064, D09722, G12879, Q7420893, 1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-4-(hexadecanoylamino)pyrimidin-2(1H)-one, 1-(2-Cyano-2-deoxy-beta-D-arabinofuranosyl)-4-hexadecanamidopyrimidin-2(1H)-one, HEXADECANAMIDE, N-(1-(2-CYANO-2-DEOXY-.BETA.-D-ARABINOFURANOSYL)-1,2-DIHYDRO-2-OXO-4- PYRIMIDINYL)-, N-(1-(2-CYANO-2-DEOXY-.BETA.-D-ARABINOFURANOSYL)-2-OXO-1,2-DIHYDROPYRIMIDIN-4- YL)HEXADECANAMIDE, N-[1-(2-Cyano-2-deoxy-|_-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]hexadecanamide, N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]hexadecanamide
Theoretical properties:
molecular_formula: C26H42N4O5
molecular_weight: 490.6 g/mol
exact_mass: 490.31552045 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 17
heavy_atom_count: 35
topological_polar_surface_area: 135 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 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.
chebi: 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).
chembl: SAPACITABINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Sapacitabine is a chemotherapeutic drug  developed by US biotechnology firm Cyclacel currently undergoing clinical trials against leukemia.
Sapacitabine is an orally available nucleoside analog prodrug of 2′-C-cyano-2′-deoxy-1-β-D-arabino-pentofuranosyl-cytosine (CNDAC) that acts through a dual mechanism. CNDAC lasts longer in the bloodstream by being metabolized from sapacitibine than it would do so by being directly administered. 
The compound interferes with DNA synthesis by causing single-strand DNA breaks due to CNDAC being incorporated into DNA during replication or repair, then inducing arrest of the cell division cycle at G2 phase.
Both sapacitabine and its major metabolite, CNDAC, have demonstrated potent anti-tumor activity in both blood and solid tumors in preclinical studies. In a liver metastatic mouse model, sapacitabine was shown to be superior to gemcitabine or 5-FU, two widely used nucleoside analogs, in delaying the onset and growth of liver metastasis.