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Sapacitabine

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ACTIVE PHARMA INGREDIENTS

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1 API Suppliers
1 USDMF

Synopsis

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Chemistry

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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

Sapacitabine

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 Formula	C₂₆H₄₂N₄O₅
Molecular Weight	490.6 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	17
Exact Mass	490.31552045 g/mol
Monoisotopic Mass	490.31552045 g/mol
Topological Polar Surface Area	135 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	775
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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