261909-26-6

Basic information

• Product Name: methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
• Synonyms: methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
• CAS NO: 261909-26-6
• Molecular Weight: 527.52
• Mol File: 261909-26-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate(261909-26-6)
• EPA Substance Registry System: methyl ((((1S,4R)-4-(2-amino-6-(cyclopropyl-amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate(261909-26-6)

Safety Data

• Hazardous Substances Data: 261909-26-6(Hazardous Substances Data)

Upstream product

• 770-12-7 O-phenyl phosphorodichloridate 
• 136470-78-5 abacavir 
• 142629-80-9 phenyl methoxyalaninyl phosphorochloridate 

Relevant articles and documents

ProTide generated long-acting abacavir nanoformulations

Abacavir pronucleotide nanoformulations (NM3ABC) were prepared as a novel long acting slow effective release antiretroviral therapy. Single NM3ABC treatment of human monocyte-derived macrophages produced sustained intracellular carbovir-triphosphate and antiretroviral activities for up to 30 days.

Application of phosphoramidate pronucleotide technology to abacavir leads to a significant enhancement of antiviral potency

We report the first application of pronucleotide (ProTide) technology to the antiviral agent abacavir (Ziagen), used for the treatment of HIV infection. The phenylmethoxyalaninyl phosphoramidate of abacavir was prepared in good yield in one step. Also prepared was the corresponding phosphoramidate of the guanine nucleoside analogue "carbovir". The antiviral profile of each of the parent nucleosides was compared to that of the phosphoramidate ProTides. A significant (28- to 60-fold) increase in anti-HIV potency was noted for the ProTide of abacavir but not for that of carbovir. These findings were in agreement with the markedly higher (ca. 37-fold) levels of carbovir triphosphate that are formed in CEM cells upon response to the abacavir ProTide compared with the parent abacavir compound. In contrast the anti-HBV potency of both abacavir and carbovir were improved (10- and 20-fold, respectively) by ProTide formation. As in CEM cells, the abacavir ProTide provided significantly enhanced carbovir triphosphate levels in HepG2 2.2.15 cells over that of the parent nucleoside. On the basis of these data, a series of phosphoramidate analogues with structural variation in the ester and amino acid regions were prepared and their antiviral profiles described. In addition, the pharmacokinetic disposition of the abacavir phenylethoxyalaninyl phosphoramidate was evaluated in Cynomolgus monkeys.