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    Sapacitabine

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 151823-14-2, Cs-682, Cyc682, Cyc-682, Cs682, Cs 682
    Molecular Formula
    C26H42N4O5
    Molecular Weight
    490.6  g/mol
    InChI Key
    LBGFKUUHOPIEMA-PEARBKPGSA-N
    FDA UNII
    W335P73C3L
    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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide
    2.1.2 InChI
    InChI=1S/C26H42N4O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(32)28-22-16-17-30(26(34)29-22)25-20(18-27)24(33)21(19-31)35-25/h16-17,20-21,24-25,31,33H,2-15,19H2,1H3,(H,28,29,32,34)/t20-,21+,24-,25+/m0/s1
    2.1.3 InChI Key
    LBGFKUUHOPIEMA-PEARBKPGSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)C#N
    2.1.5 Isomeric SMILES
    CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)C#N
    2.2 Other Identifiers
    2.2.1 UNII
    W335P73C3L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2'-c-cyano-2'-deoxy-1-arabinofuranosyl-n(4)-palmitoylcytosine

    2. Cndac Cpd

    3. Cs-682

    4. Cyc 682

    5. Cyc-682

    2.3.2 Depositor-Supplied Synonyms

    1. 151823-14-2

    2. Cs-682

    3. Cyc682

    4. Cyc-682

    5. Cs682

    6. Cs 682

    7. Pcndac

    8. Cyc 682

    9. W335p73c3l

    10. N-(1-(2-cyano-2-deoxy-beta-d-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl)hexadecanamide

    11. N-(1-((2r,3s,4s,5r)-3-cyano-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)palmitamide

    12. Sapacitabine [usan:inn]

    13. Sapacitabina

    14. Sapacitabinum

    15. Unii-w335p73c3l

    16. Sapacitabine (cyc682)

    17. Sapacitabine (usan/inn)

    18. Sapacitabine [inn]

    19. Sapacitabine [usan]

    20. Sapacitabine [mart.]

    21. N-[1-[(2r,3s,4s,5r)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide

    22. Sapacitabine [who-dd]

    23. Schembl711854

    24. Chembl2105681

    25. Dtxsid90164887

    26. Chebi:145429

    27. Ex-a1617

    28. Nsc791785

    29. Zinc14263648

    30. Db06365

    31. Nsc-791785

    32. Ac-36130

    33. Hexadecanamide, N-(1-(2-cyano-2-deoxy-beta-d-arabinofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl)-

    34. Hy-16445

    35. Cs-0006340

    36. D09722

    37. 823s142

    38. Q7420893

    39. 2'-c-cyano-2'-deoxy-1-arabinofuranosyl-n(4)-palmitoylcytosine

    40. 1-(2-cyano-2-deoxy-beta-d-arabinofuranosyl)-4-(hexadecanoylamino)pyrimidin-2(1h)-one

    41. Hexadecanamide, N-(1-(2-cyano-2-deoxy-.beta.-d-arabinofuranosyl)-1,2-dihydro-2-oxo-4- Pyrimidinyl)-

    42. N-(1-(2-cyano-2-deoxy-.beta.-d-arabinofuranosyl)-2-oxo-1,2-dihydropyrimidin-4- Yl)hexadecanamide

    43. N-[1-(2-cyano-2-deoxy-beta-d-arabinofuranosyl)-2-oxo-1,2-dihydropyrimidine-4-yl]hexadecanamide

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 490.6 g/mol
    Molecular Formula C26H42N4O5
    XLogP35.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count17
    Exact Mass490.31552045 g/mol
    Monoisotopic Mass490.31552045 g/mol
    Topological Polar Surface Area135 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity775
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in solid tumors, cutaneous t-cell lymphoma, myelodysplastic syndrome, and leukemia (lymphoid).

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    5.2 Mechanism of Action

    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.