Sapacitabine
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Sapacitabine
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CAS No:
151823-14-2
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Formula:
C26H42N4O5
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Chemical Name:
Sapacitabine
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Synonyms:
Hexadecanamide,N-[1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]-;N-[1-(2-Cyano-2-deoxy-β-D-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]hexadecanamide;CS 682;Sapacitabine;CYC 682
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CAS No:
Description
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 derives from a hexadecanoic acid and a CNDAC.|Sapacitabine is an orally bioavailable pyrimidine analogue prodrug with potential antineoplastic activity. Sapacitabine is hydrolyzed by amidases to the deoxycytosine analogue CNDAC (2'-Cyano-2'-deoxyarabinofuranosylcytosine), which is then phosphorylated into the active triphosphate form. As an analogue of deoxycytidine triphosphate, CNDAC triphosphate incorporates into DNA strands during replication, resulting in single-stranded DNA breaks during polymerization due to beta-elimination during the fidelity checkpoint process; cell cycle arrest in the G2 phase and apoptosis ensue. The unmetabolized prodrug may exhibit antineoplastic activity as well.
Drug Information
Investigated for use/treatment in solid tumors, cutaneous t-cell lymphoma, myelodysplastic syndrome, and leukemia (lymphoid).
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
Sapacitabine appears to act through a dual mechanism. It interferes with DNA synthesis by causing single-strand DNA breaks and also induces arrest of cell cycle progression mainly at G2/M-Phase. Both sapacitabine and CNDAC, its major metabolite or a substance into which the drugs converts after ingestion by patients, have demonstrated potent anti-tumor activity in preclinical studies.
2'-C-cyano-2'-deoxy-1-arabinofuranosyl-N(4)-palmitoylcytosine
Computed Properties
Molecular Weight:490.6
XLogP3:5.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:17
Exact Mass:490.31552045
Monoisotopic Mass:490.31552045
Topological Polar Surface Area:135
Heavy Atom Count:35
Complexity:775
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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