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Synopsis

Synopsis

ACTIVE PHARMA INGREDIENTS

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JDMF

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EU WC

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NDC API

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NDC API

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Listed Suppliers

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API REF. PRICE (USD/KG)

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$ 0

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API

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FDF

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Europe

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Canada

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Australia

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Listed Dossiers

Listed Dossiers

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DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

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EDQM

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USP

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JP

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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
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 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.


ABOUT THIS PAGE

Sapacitabine Manufacturers

A Sapacitabine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Sapacitabine, including repackagers and relabelers. The FDA regulates Sapacitabine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Sapacitabine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Sapacitabine Suppliers

A Sapacitabine supplier is an individual or a company that provides Sapacitabine active pharmaceutical ingredient (API) or Sapacitabine finished formulations upon request. The Sapacitabine suppliers may include Sapacitabine API manufacturers, exporters, distributors and traders.

click here to find a list of Sapacitabine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Sapacitabine USDMF

A Sapacitabine DMF (Drug Master File) is a document detailing the whole manufacturing process of Sapacitabine active pharmaceutical ingredient (API) in detail. Different forms of Sapacitabine DMFs exist exist since differing nations have different regulations, such as Sapacitabine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Sapacitabine DMF submitted to regulatory agencies in the US is known as a USDMF. Sapacitabine USDMF includes data on Sapacitabine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Sapacitabine USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Sapacitabine suppliers with USDMF on PharmaCompass.

Sapacitabine GMP

Sapacitabine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Sapacitabine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Sapacitabine GMP manufacturer or Sapacitabine GMP API supplier for your needs.

Sapacitabine CoA

A Sapacitabine CoA (Certificate of Analysis) is a formal document that attests to Sapacitabine's compliance with Sapacitabine specifications and serves as a tool for batch-level quality control.

Sapacitabine CoA mostly includes findings from lab analyses of a specific batch. For each Sapacitabine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Sapacitabine may be tested according to a variety of international standards, such as European Pharmacopoeia (Sapacitabine EP), Sapacitabine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Sapacitabine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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