Entecavir monohydrate

Names

[ CAS No. ]:
209216-23-9

[ Name ]:
Entecavir monohydrate

[Synonym ]:
Entecavirhydrate
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidencyclopentyl]-1,9-dihydro-6H-purin-6-onhydrat
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one hydrate
Entecavir hydrate
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxyméthyl)-2-méthylidènecyclopentyl]-1,9-dihydro-6H-purin-6-one hydrate
6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-, hydrate (1:1)
entecavir
Entecavir Monohydrate IsoMers
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one hydrate (1:1)
BMS 200475-01
2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one Monohydrate
9-[(1S,3R,4S)-4-Hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]guanine Monohydrate
Entecavir (monohydrate)
Entecavir monohydrate
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one hydrate
6H-purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-, monohydrate
9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-guanine Monohydrate
6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-, monohydrate

Biological Activity

[Description]:

Entecavir monohydrate (SQ 34676; BMS 200475) is a potent and selective inhibitor of HBV, with an EC50 of 3.75 nM in HepG2 cell.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HBV

Research Areas >> Infection

[Target]

EC50：3.75 nM (anti-HBV, HepG2 cell)[1]

[In Vitro]

BMS-200475 has a EC50 of 3.75 nM against HBV. It is incorporated into the protein primer of HBV and subsequently inhibits the priming step of the reverse transcriptase. The antiviral activity of BMS-200475 is significantly less against the other RNA and DNA viruses[1]. Entecavir is more readily phosphorylated to its active metabolites than other deoxyguanosine analogs (penciclovir, ganciclovir, lobucavir, and aciclovir) or lamivudine. The intracellular half-life of entecavir is 15 h[2].

[In Vivo]

Daily oral treatment with BMS-200475 at doses ranging from 0.02 to 0.5 mg/kg of body weight for 1 to 3 months effectively reduces the level of woodchuck hepatitis virus (WHV) viremia in chronically infected woodchucks[3].

[Cell Assay]

BMS 200475 is prepared in phosphate-buffered saline (PBS) and diluted with appropriate medium containing 2% fetal bovine serum. HepG2 2.2.15 cells are plated at a density of 5×105 cells per well on 12-well Biocoat collagen-coated plates and are maintained in a confluent state for 2 to 3 days before being overlaid with 1 mL of medium spiked with BMS 200475. Quantification of HBV was performed on day 10[1].

[References]

[1]. Innaimo SF, et al. Identification of?BMS-200475?as a potent and selective inhibitor of hepatitis B virus. Antimicrob Agents Chemother. 1997 Jul;41(7):1444-8.

[2]. Rivkin A, et al. A review of entecavir in the treatment of chronic hepatitis B infection. Curr Med Res Opin.?2005 Nov;21(11):1845-56.

[3]. Genovesi EV, et al. Efficacy of the carbocyclic 2'-deoxyguanosine nucleoside?BMS-200475?in the woodchuck model of hepatitis B virus infection. Antimicrob Agents Chemother.?1998 Dec;42(12):3209-17.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.81

[ Boiling Point ]:
661.4ºC at 760 mmHg

[ Melting Point ]:
259 °C(dec.)

[ Molecular Formula ]:
C₁₂H₁₇N₅O₄

[ Molecular Weight ]:
295.294

[ Exact Mass ]:
295.128052

[ PSA ]:
139.28000

[ Vapour Pressure ]:
2.15E-18mmHg at 25°C

[ Storage condition ]:
2-8°C

Safety Information

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%