Size | Price | Stock | Qty |
---|---|---|---|
5mg |
|
||
10mg |
|
||
25mg |
|
||
50mg |
|
||
100mg |
|
||
250mg |
|
||
500mg |
|
||
Other Sizes |
|
Purity: ≥98%
Targets |
anti-HBV, HepG2 cell(EC50=3.75 nM)
|
||
---|---|---|---|
ln Vitro |
Entecavir-triphosphate is a highly potent inhibitor of wild-type HBV Pol and is 100- to 300-fold more potent than lamivudine-triphosphate against 3TC-resistant HBV Pol. Entecavir inhibits the replication of 3TC-resistant HBV, but 20- to 30-fold higher concentrations are required. Entecavir results in an impressive reduction of serum viral DNA with covalently closed circular DNA and hepatitis B viral core antigen negativity in liver biopsy specimens. Entecavir has potent activity (EC50, 0.1 nM) against HIV in a unique single-cycle, single-cell-based pseudovirus assay (24) with CD4+ lymphocytes using a green fluorescent protein reporter fluorescence-activated cell sorter assay as the endpoint.
|
||
ln Vivo |
|
||
Enzyme Assay |
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. 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.
|
||
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.
|
||
Animal Protocol |
|
||
References | |||
Additional Infomation |
Entecavir (anhydrous) is guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B. It has a role as an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor and an antiviral drug. It is a member of 2-aminopurines, an oxopurine, a primary alcohol and a secondary alcohol.
Entecavir is an antiviral prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of chronic hepatitis B virus infection (HBV) in adults and children 2 years of age and older who meet certain requirements, as determined by a health care provider. HBV can be an opportunistic infection (OI) of HIV. Entecavir is an oral antiviral drug used in the treatment of hepatitis B infection. It is marketed under the trade name Baraclude (BMS). Entecavir is a guanine analogue that inhibits all three steps in the viral replication process, and the manufacturer claims that it is more efficacious than previous agents used to treat hepatitis B (lamivudine and adefovir). It was approved by the U.S. Food and Drug Administration (FDA) in March 2005. Entecavir anhydrous is a Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of entecavir anhydrous is as a Nucleoside Reverse Transcriptase Inhibitor. Entecavir is a guanosine nucleoside analogue used in the treatment of chronic hepatitis B virus (HBV) infection. Entecavir therapy can be associated with flares of the underlying hepatitis B during or after therapy, but has not been linked to cases of clinically apparent liver injury. Entecavir is a synthetic analog of 2-deoxyguanosine with antiviral activity against hepatitis B virus (HBV). Entecavir is activated in vivo to a 5-triphosphate metabolite. In turn, the triphosphate form competes with the natural substrate deoxyguanosine triphosphate (dGTP) for incorporation into viral DNA. The incorporation of the activated triphosphate metabolite of entecavir inhibits the reverse transcriptase (RT) viral RNA-dependent HBV DNA polymerase and, so, the replication of viral DNA and transcription. Entecavir Anhydrous is an anhydrous formulation of entecavir, a synthetic analog of 2-deoxyguanosine with antiviral activity against hepatitis B virus (HBV). Entecavir is activated in vivo to a 5-triphosphate metabolite. In turn, the triphosphate form competes with the natural substrate deoxyguanosine triphosphate (dGTP) for incorporation into viral DNA. The incorporation of the activated triphosphate metabolite of entecavir inhibits the reverse transcriptase (RT) viral RNA-dependent HBV DNA polymerase and, so, the replication of viral DNA and transcription. |
Molecular Formula |
C12H15N5O3
|
---|---|
Molecular Weight |
277.28
|
Exact Mass |
277.12
|
Elemental Analysis |
C, 51.98; H, 5.45; N, 25.26; O, 17.31
|
CAS # |
142217-69-4
|
Related CAS # |
Entecavir monohydrate;209216-23-9;Entecavir-13C2,15N;(1R,3S,4R)-ent-Entecavir;188399-46-4;Entecavir-d2
|
PubChem CID |
135398508
|
Appearance |
White to off-white solid powder
|
Density |
1.8±0.1 g/cm3
|
Boiling Point |
734.2ºC at 760 mmHg
|
Melting Point |
249-252ºC
|
Flash Point |
397.9ºC
|
Index of Refraction |
1.837
|
LogP |
-0.96
|
tPSA |
130.050
|
SMILES |
O=C1N=C(N)NC2=C1N=CN2[C@@H]3C([C@H](CO)[C@@H](O)C3)=C
|
InChi Key |
QDGZDCVAUDNJFG-FXQIFTODSA-N
|
InChi Code |
InChI=1S/C12H15N5O3/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)/t6-,7-,8-/m0/s1
|
Chemical Name |
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one
|
Synonyms |
Entecavir; Baraclude; BMS-200475; BMS-200475; BMS-200475; FT-0083013; FT0083013; FT0083013; D07896; SQ 34676; SQ-34676; SQ34676;
|
HS Tariff Code |
2934.99.9001
|
Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
Solubility (In Vitro) |
DMSO : ≥ 44~55 mg/mL (158.68~198.35 mM)
|
---|---|
Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 3.6065 mL | 18.0323 mL | 36.0646 mL | |
5 mM | 0.7213 mL | 3.6065 mL | 7.2129 mL | |
10 mM | 0.3606 mL | 1.8032 mL | 3.6065 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Detection of DHBV DNA (A) and DHBsAg (B) in the serum of ducks in groups 1 (ETV plus DHBV vaccine), 2 (ETV plus vector), 3 (water plus DHBV vaccine), and 4 (water plus vector). [2]. Antimicrob Agents Chemother.2003 Aug;47(8):2624-35. td> |
Liver tissue was extracted for total and cccDNA and then subjected to Southern blot hybridization using a 32P-labeled genome-length DHBV DNA probe. [2]. Antimicrob Agents Chemother.2003 Aug;47(8):2624-35. td> |
ETV treatment reduced the percentage of liver cells that contained detectable levels of DHBsAg.[2]. Antimicrob Agents Chemother.2003 Aug;47(8):2624-35. td> |
Detection of DHBsAg-positive cells in liver by indirect immunoperoxidase staining of ethanol-acetic acid-fixed liver tissue counterstained with hematoxylin from an ETV-treated duck from group 1 (167168) on day 287. [2]. Antimicrob Agents Chemother.2003 Aug;47(8):2624-35. td> |
(A to C) Average levels of the liver function enzymes GGT (A), AST (B), and ALT (C) in serum collected at weekly intervals for all ducks in groups 1 to 5. (D) Average body weights for all ducks in each group are shown at weekly intervals.[2]. Antimicrob Agents Chemother.2003 Aug;47(8):2624-35. td> |