Entecavir Hydrate

Antiviral drug used in hepatitis B infection CAS# 209216-23-9

Entecavir Hydrate

Catalog No. BCC1109----Order now to get a substantial discount!

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Entecavir Hydrate: 5mg $92 In Stock
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Chemical structure

Entecavir Hydrate

3D structure

Chemical Properties of Entecavir Hydrate

Cas No. 209216-23-9 SDF Download SDF
PubChem ID 170342 Appearance Powder
Formula C12H15N5O3.H2O M.Wt 295.29
Type of Compound N/A Storage Desiccate at -20°C
Synonyms SQ 34676; BMS-200475
Solubility DMSO : ≥ 50 mg/mL (169.33 mM)
H2O : 2.8 mg/mL (9.48 mM; Need ultrasonic and warming)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-amino-9-[(3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one;hydrate
SMILES C=C1C(CC(C1CO)O)N2C=NC3=C2NC(=NC3=O)N.O
Standard InChIKey YXPVEXCTPGULBZ-JBDQBEHPSA-N
Standard InChI InChI=1S/C12H15N5O3.H2O/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20;/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20);1H2/t6-,7?,8-;/m0./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Entecavir Hydrate

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

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.

Protocol

Cell Assay [1]
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.

Entecavir Hydrate Dilution Calculator

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Entecavir Hydrate Molarity Calculator

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Preparing Stock Solutions of Entecavir Hydrate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3865 mL 16.9325 mL 33.865 mL 67.73 mL 84.6625 mL
5 mM 0.6773 mL 3.3865 mL 6.773 mL 13.546 mL 16.9325 mL
10 mM 0.3387 mL 1.6933 mL 3.3865 mL 6.773 mL 8.4663 mL
50 mM 0.0677 mL 0.3387 mL 0.6773 mL 1.3546 mL 1.6933 mL
100 mM 0.0339 mL 0.1693 mL 0.3387 mL 0.6773 mL 0.8466 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Entecavir Hydrate

Entecavir hydrate is a reverse transcriptase inhibitor.
Reverse transcriptase (RT) is used to generate complementary DNA (cDNA) from an RNA template, which is mainly associated with retroviruses, such as HBV.
Entecavir hydrate is an oral antiviral drug used in the treatment of hepatitis B virus (HBV) infection. In 17 patients with hepatitis B virus (HBV) genotype C, treatment with peginterferon
(PEG-IFN) a-2b combination with entecavir hydrate (ETV) for 48 weeks. Among 11 patients exhibited pretherapy HBeAg, 8 showed HBeAg seroconversion. Serum HBV DNA levels reduced by 5.2 and 3.3 log copies/ml by the end of the therapy and follow-up periods, respectively. Intrahepatic cccDNA reduced to 1.4 log copies/mg.  
References:
[1]. Hagiwara S, Kudo M, Osaki Y, et al. Impact of peginterferon alpha-2b and entecavir hydrate combination therapy on persistent viral suppression in patients with chronic hepatitis B. J Med Virol, 2013, 85(6): 987-995.

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References on Entecavir Hydrate

Impact of peginterferon alpha-2b and entecavir hydrate combination therapy on persistent viral suppression in patients with chronic hepatitis B.[Pubmed:23588724]

J Med Virol. 2013 Jun;85(6):987-95.

The ideal approach to treat chronic hepatitis B remains controversial. This pilot study aimed to evaluate the effectiveness of peginterferon (PEG-IFN) alpha-2b and Entecavir Hydrate (ETV) as a combination therapy for patients with chronic hepatitis B, particularly in the context of virological response and the reduction of intrahepatic covalently closed circular DNA (cccDNA). A total of 17 patients with hepatitis B virus (HBV) genotype C were enrolled in this study. All subjects were treated with this combination therapy for 48 weeks and observed for an additional 24 weeks. All patients underwent liver biopsy before and after the therapy period. Changes in cccDNA levels and liver histology were monitored between biopsies. Among the 11 patients who exhibited pre-therapy hepatitis B e antigen (HBeAg), 8 (73%) showed evidence of HBeAg seroconversion by the end of the follow-up period. Serum HBV DNA levels decreased by 5.2 and 3.3 log copies/ml (mean) by the end of the therapy and follow-up periods, respectively. In addition, intrahepatic cccDNA decreased significantly to 1.4 log copies/microg (mean) by the end of the therapy period. Among the 11 patients who did not experience viral relapse, only 2 (18%) exhibited high levels of cccDNA (>4.5 log copies/microg) by the end of the treatment period. In contrast, all relapsed subjects exhibited significantly higher levels of cccDNA than subjects who did not relapse (P = 0.027). The combination regimen is a promising approach to treat chronic hepatitis B and may achieve significant reduction in serum HBV DNA and intrahepatic cccDNA. Wiley Periodicals, Inc.

Description

Entecavir monohydrate (BMS200475 monohydrate; SQ34676 monohydrate) is a potent and selective inhibitor of HBV, with an EC50 of 3.75 nM in HepG2 cell.

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