Sapacitabine - ≥98% , DNA inhibitor, CAS No.151823-14-2, DNA inhibitor

CAS: 151823-14-2 Cat. No.: S649020 Formula: C₂₆H₄₂N₄O₅ Molecular Weight: 490.64 PubChem CID: 153970

GRADE & PURITY ≥98%

Synonyms

2'-C-cyano-2'-deoxy-1-arabinofuranosyl-N(4)-palmitoylcytosine | N-(1-((2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)palmitamide | SAPACITABINE [USAN] | 1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-4-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Sapacitabine is an orally available nucleoside analog proagent that is structurally related to cytarabine.

In Vitro

Concentrations of Sapacitabine required to achieve an IC 50 range from 3±0.6 μM for the colon cancer cell line HCT116 to 67±14 μM for the breast cancer cell line MDA-MB-435. Cell cycle analysis shows that 35% Sapacitabine-treated cells are arrested in late-S phase and 41% in G 2 /M phase. L1210 cells with deoxycytidine kinase (dCK) activity are sensitive to Sapacitabine, (IC 50 20±6 μM). In the docetaxel/Sapacitabine combinations, synergistic effects (CI<1) are observed when docetaxel is given before Sapacitabine in both cell lines. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

On Day 14, the Sapacitabine (5 mg/kg)+vorinostat (33 mg/kg) group has a mean tumour volume of 245 mm 3 and a tumour growth inhibition (TGI) of 92%, whereas the Sapacitabine (15 mg/kg)+vorinostat (33 mg/kg) group has a mean tumour volume of 107 mm 3 and a TGI of 112%. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Animal administration

Female (nu/nu) mice are injected subcutaneously with 1×10 7 MV4-11 cells resuspended in 50% Matrigel at a single site on their flanks. Once tumour volumes are 126 to 256 mm 3 (16 days post-implantation) animals are pair matched by tumour size into treatment groups (minimum of six mice per group) with a mean tumour size of ~190 mm 3 . Tumour measurements are calculated using the formula: volume (mm 3 )=width 2 (mm)×length (mm)×0.5. Sapacitabine is administered once a day orally (5 or 15 mg/kg) for 4 days , followed by a 3-day break before another 4 days of treatment; dosing starts on the same day as distribution to the treatment groups . aladdin has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:nucleoside analog

Specifications

Synonyms

2'-C-cyano-2'-deoxy-1-arabinofuranosyl-N(4)-palmitoylcytosine | N-(1-((2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)palmitamide | SAPACITABINE [USAN] | 1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)-4-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Sapacitabine is an orally available nucleoside analog proagent that is structurally related to cytarabine.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

DNA inhibitor

Purity

≥98%

Product Properties

• ALogP: 5.2

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)C2C(C(C(O2)CO)O)C#N
• IUPAC Name: N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide
• InChIKey: LBGFKUUHOPIEMA-PEARBKPGSA-N
• 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
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)C#N
• Alternate CAS: 151823-14-2
• PubChem CID: 153970
• MeSH Entry Terms: 2'-C-cyano-2'-deoxy-1-arabinofuranosyl-N(4)-palmitoylcytosine;CNDAC cpd;CS-682;CYC 682;CYC-682;sapacitabine
• Molecular Weight: 490.64

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Pyrimidine nucleosides
      • Subclass Pyrimidine 2'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Pyrimidine nucleosides
• Subclass: Pyrimidine 2'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine 2'-deoxyribonucleosides
• Alternative Parents: N-arylamides Pyrimidones Fatty amides Imidolactams Hydropyrimidines Tetrahydrofurans Heteroaromatic compounds Secondary carboxylic acid amides Secondary alcohols Azacyclic compounds Oxacyclic compounds Nitriles Hydrocarbon derivatives Organic oxides Organopnictogen compounds Carbonyl compounds Primary alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - N-arylamide - Pyrimidone - Fatty amide - Hydropyrimidine - Pyrimidine - Fatty acyl - Imidolactam - Heteroaromatic compound - Tetrahydrofuran - Carboxamide group - Secondary alcohol - Secondary carboxylic acid amide - Carboxylic acid derivative - Carbonitrile - Nitrile - Oxacycle - Azacycle - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organopnictogen compound - Primary alcohol - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Alcohol - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 33.33 mg/mL (67.93 mM; Need ultrasonic)
• Molecular Weight: 490.600 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 17
• Exact Mass: 490.316 Da
• Monoisotopic Mass: 490.316 Da
• Topological Polar Surface Area: 135.000 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 775.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 151823-14-2, the molecular formula is C26H42N4O5, and the molecular weight is 490.64 g/mol. InChIKey LBGFKUUHOPIEMA-PEARBKPGSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.