3595. Entecavir

Nomenclature

CAS number: 142217-69-4
2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one.
C12H15N5O3; mol wt 277.28.
C 51.98%, H 5.45%, N 25.26%, O 17.31%.

Description and references

Deoxyguanine nucleoside analog; inhibits hepatitis B virus (HBV) DNA polymerase. Prepn: R. Zahler, W. A. Slusarchyk, EP 481754; eidem, US 5206244 (1992, 1993 both to Squibb); G. S. Bisacchi et al., Bioorg. Med. Chem. Lett. 7, 127 (1997). In vitro antiviral activity: S. F. Innaimo et al, Antimicrob. Agents Chemother. 41, 1444 (1997). Review of pharmacology and clinical experience: P. Honkoop, R. A. de Man, Expert Opin. Invest. Drugs 12, 683-688 (2003); T. Shaw, S. Locarnini, Expert Rev. Anti Infect. Ther. 2, 853-871 (2004). Clinical comparisons with lamivudine in chronic hepatitis B: T.-T. Chang et al., N. Engl. J. Med. 354, 1001 (2006); C.-L. Lai et al., ibid. 1011.

Chemical structure

Derivative

Monohydrate.

Nomenclature

CAS number: 209216-23-9
BMS-200475; SQ-200475; Baraclude (BMS).
C12H15N5O3.H2O; mol wt 295.29.
C 48.81%, H 5.80%, N 23.72%, O 21.67%.

Properties

White to off-white powder, mp >220°. [α]D +35.0° (c = 0.38 in water). Soly in water: 2.4 mg/ml. pH of saturated soln in water is 7.9 at 25°±0.5°.

Therapeutic Category

Antiviral.

Keywords

Antiviral; Nucleosides/Nucleotides