恩替卡韦, Entecavir

Entecavir is an antiviral nucleoside analog of 2'-deoxyguanosine and inhibitor of hepatitis B virus (HBV) reverse transcriptase (IC50 = 0.5 nM). It undergoes phosphorylation by cellular kinases to its active form, entecavir triphosphate. Entecavir reduces virion DNA in the culture supernatant of HepG2 2.2. 5 cells infected with hepatitis B virus (HBV; EC50 = 3.75 nM). It reduces serum and hepatic levels of viral DNA in a duckling model of HBV infection when administered at a dose of 1 mg/kg. Formulations containing entecavir have been used in the treatment of chronic HBV infection.

Entecavir is an oral antiviral drug used in the treatment of hepatitis B virus (HBV) infection. Entecavir is a reverse transcriptase inhibitor. It prevents the hepatitis B virus from multiplying and reduces the amount of virus in the body. More specifically, it is a deoxyguanosine analogue belonging to a class of carbocyclic nucleosides, that inhibits reverse transcription, DNA replication and transcription in the viral replication process.

Title: Entecavir

CAS Registry Number: 142217-69-4

CAS Name: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one

Molecular Formula: C12H15N5O3

Molecular Weight: 277.28

Percent Composition: C 51.98%, H 5.45%, N 25.26%, O 17.31%

Literature 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.

Derivative Type: Monohydrate

CAS Registry Number: 209216-23-9

Manufacturers' Codes: BMS-200475; SQ-200475

Trademarks: Baraclude (BMS)

Molecular Formula: C12H15N5O3.H2O

Molecular Weight: 295.29

Percent Composition: C 48.81%, H 5.80%, N 23.72%, O 21.67%

Properties: White to off-white powder, mp >220°. [a]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°.

Melting point: mp >220°

Optical Rotation: [a]D +35.0° (c = 0.38 in water)

Therap-Cat: Antiviral.

Keywords: Antiviral; Purines/Pyrimidinones.