151823-14-2

Basic information

• Product Name: Sapacitabine
• Synonyms: N-[1-[(2R,3S,4S,5R)-3-cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2- oxo-pyrimidin-4-yl]hexadecanamide;CS-682;Sapacitabine;1-(2-C-Cyano-2-deoxy-β-D-arabino-pentofuranosyl)cytosine;1-(2-Deoxy-2-cyano-β-D-arabinofuranosyl)cytosine;4-Amino-1-[(3β-cyano-4α-hydroxy-5β-hydroxymethyltetrahydrofuran)-2β-yl]pyrimidin-2(1H)-one;CNDAC;1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-4-(palMitoylaMino)pyriMidin-2(1H)-one,Sapacitabine
• CAS NO: 151823-14-2
• Molecular Formula: C26H42N4O5
• Molecular Weight: 490.63
• Mol File: 151823-14-2.mol

Chemical Properties

• Appearance: /
• Density: 1.21 g/cm³
• Refractive Index: 1.574
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 10.04±0.20(Predicted)
• CAS DataBase Reference: Sapacitabine(CAS DataBase Reference)
• NIST Chemistry Reference: Sapacitabine(151823-14-2)
• EPA Substance Registry System: Sapacitabine(151823-14-2)

Safety Data

• Hazardous Substances Data: 151823-14-2(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Sapacitabine is used as a chemotherapy agent for its potential in treating various types of cancer. It acts through a dual mechanism, which allows it to be effective against cancer cells and contribute to tumor growth inhibition and progression.
Used in Drug Development:
Sapacitabine is used as a pharmaceutical candidate in drug development due to its unique dual mechanism of action. This characteristic makes it a valuable asset in the creation of new cancer treatment options and potentially improving the efficacy of existing treatments.
Used in Clinical Trials:
Sapacitabine is used as a subject in clinical trials to evaluate its safety, efficacy, and potential side effects when used as a chemotherapy agent. These trials are essential in determining the drug's suitability for widespread use in cancer treatment.

Biochem/physiol Actions

Sapacitabine is an orally active prodrug of nucleoside analog CNDAC that exhibits potent anti-tumor activity in both blood and solid tumors. CNDAC incorporates into DNA where it causes single-strand breaks (SSBs), which are converted into double strand breaks (DSBs) during S phase.

InChI:InChI=1/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

Upstream product

• 623-65-4 palmitic anhydride 
• 135598-68-4 1-(2-cyano-2-deoxy-beta-D-arabinofuranosyl)cytosine 

Relevant articles and documents

PREPARATION OF INTERMEDIATES USEFUL IN THE SYNTHEIS OF 2'-CYANO-2'-DEOXY-N4-PALMITOYL-1-BETA-D-ARABINOFURANOSYLCYTOSINE

The present invention relates to a process for preparing a compound of formula 682-4, said process comprising the steps of: (i) converting a compound of formula 682-1 into a compound of formula 682-2'; (ii) converting said compound of formula 682-2' into a compound of formula 682-3; and (iii) converting said compound of formula 682-3 into a compound of formula 682-4. Further aspects of the invention relate to the use of the above process in the preparation of 2'-cyano-2'-deoxy-N4 -palmitoyl-1-β-D-arabmofuranosylcytosine, a pyrimidine nucleoside which is therapeutically useful in the treatment and/or prevention of cancer.

INTERMEDIATE AND PROCESSES INVOLVED IN THE PREPARATION OF 2 ' -CYANO-2 ' -DE0XY-N4-PALMIT0YL-1-BETA-ARABIN0FURAN0SYLCYTOSINE

The present invention relates to a process for preparing a compound of formula (682-6'), said process comprising the steps of: formula (682-4), (682-5), (682-6'): (i) converting a compound of formula (682-4) into a compound of formula (682-5); and (ii) converting said compound of formula (682-5) into a compound of formula (682- 6'). Further aspects of the invention relate to the use of the above process in the preparation of 2'-cyano-2'-deoxy-N4-palmitoyl-l-β-D-arabinofuranosylcytosine, a pyrimidine nucleoside which is therapeutically useful in the treatment and/or prevention of cancer.

Pyrimidine nucleoside derivatives having anti-tumor activity, their preparation and use

Compounds of formula (I): STR1 wherein: R1, R2 and R3 are independently selected from the group consisting of hydrogen atoms, optionally substituted alkanoyl groups and alkenylcarbonyl groups, PROVIDED THAT at least one of R1, R2 and R3 represents an unsubstituted alkanoyl group having from 5 to 24 carbon atoms, said substituted alkanoyl group or said alkenylcarbonyl group; and one of R4 and R5 represents a hydrogen atom and the other represents a cyano group; have valuable anti-tumor activity.