55726-42-6

Basic information

• Product Name: 1-β-D-Arabinofuranosyl-4-lauroylaminopyrimidin-2(1H)-one
• Synonyms: 1-β-D-Arabinofuranosyl-4-lauroylaminopyrimidin-2(1H)-one
• CAS NO: 55726-42-6
• Molecular Formula: C21H35N3O6
• Molecular Weight: 425.522
• Mol File: 55726-42-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.3g/cm³
• Refractive Index: 1.589
• PKA: 10.14±0.20(Predicted)
• CAS DataBase Reference: 1-β-D-Arabinofuranosyl-4-lauroylaminopyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-β-D-Arabinofuranosyl-4-lauroylaminopyrimidin-2(1H)-one(55726-42-6)
• EPA Substance Registry System: 1-β-D-Arabinofuranosyl-4-lauroylaminopyrimidin-2(1H)-one(55726-42-6)

Safety Data

• Hazardous Substances Data: 55726-42-6(Hazardous Substances Data)

Usage

General Description

1-β-D-Arabinofuranosyl-4-lauroylaminopyrimidin-2(1H)-one, also known as LA-4-ara-C, is a synthetic derivative of cytarabine, a commonly used chemotherapy drug. LA-4-ara-C is designed to be more lipophilic and have increased membrane permeability compared to cytarabine, which may enhance its effectiveness in treating certain cancers. It is believed to work by inhibiting DNA synthesis in cancer cells, ultimately leading to cell death. LA-4-ara-C has been studied for its potential use in the treatment of various solid tumors and leukemia, and is undergoing further research to determine its efficacy and safety in clinical settings.

InChI:InChI=1/C21H35N3O6/c1-2-3-4-5-6-7-8-9-10-11-17(26)22-16-12-13-24(21(29)23-16)20-19(28)18(27)15(14-25)30-20/h12-13,15,18-20,25,27-28H,2-11,14H2,1H3,(H,22,23,26,29)/t15-,18-,19+,20-/m1/s1

Upstream product

• 143-07-7 lauric acid 
• 147-94-4 arabinosyl cytosine 

Relevant articles and documents

Highly enhanced leukemia therapy and oral bioavailability from a novel amphiphilic prodrug of cytarabine

Cytarabine (1-β-d-arabinofuranosylcytosine, Ara-C), an attractive medicinal treatment for myeloblastic leukemia, is subject to low oral bioavailability due to its weak membrane permeability and lipophilicity as well as its poor metabolic stability. Based on these considerations, we proposed a chemical linkage of cytarabine with lauric acid (LA), a long-chain fatty acid with 12 carbons, leading to a new prodrug, LA-Ara. The NH2 group of Ara-C is protected by conjugation and thus cannot not be deactivated by deamination; moreover, notably high liposolubility and penetrability were obtained. When dispersed in water, this new amphiphilic molecule can adopt a nanofiber configuration. It was found that LA-Ara molecules are stable in artificial biological media, indicating that the prodrug could be administrated orally. MTT assays on HL60 and K562 cells were performed, and the significantly higher cytotoxicity compared to the pure drug suggested that the prodrug has conspicuously superior antiproliferative activity. Following oral administration, the elimination half-life and bioavailability of the LA-Ara group dramatically increased to 6.6- and 32.8-fold of those of free Ara-C, respectively. It appears that this new prodrug could be an effective oral alternative treatment to Ara-C and supply a promising therapy index for leucocythemia.