CAS 142217-69-4|Entecavir
| Common Name | Entecavir | ||
|---|---|---|---|
| CAS Number | 142217-69-4 | Molecular Weight | 277.279 |
| Density | 1.8±0.1 g/cm3 | Boiling Point | 734.2ºC at 760 mmHg |
| Molecular Formula | C12H15N5O3 | Melting Point | 249-252ºC |
| MSDS | USA | Flash Point | 397.9ºC |
Names
| Name | entecavir (anhydrous) |
|---|---|
| Synonym | More Synonyms |
Entecavir BiologicalActivity
| Description | Entecavir (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 >>HBVResearch Areas >>Infection |
| Target | EC50: 3.75 nM (anti-HBV, HepG2 cell)[2] |
| 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):1444-9. [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):1845-57. [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):3209-18. |
Chemical & Physical Properties
| Density | 1.8±0.1 g/cm3 |
|---|---|
| Boiling Point | 734.2ºC at 760 mmHg |
| Melting Point | 249-252ºC |
| Molecular Formula | C12H15N5O3 |
| Molecular Weight | 277.279 |
| Flash Point | 397.9ºC |
| Exact Mass | 277.117493 |
| PSA | 130.05000 |
| LogP | -0.96 |
| Index of Refraction | 1.837 |
| InChIKey | QDGZDCVAUDNJFG-FXQIFTODSA-N |
| SMILES | C=C1C(CO)C(O)CC1n1cnc2c(=O)[nH]c(N)nc21 |
| Storage condition | -20°C Freezer |
Safety Information
| RIDADR | NONH for all modes of transport |
|---|---|
| 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% |
Articles18
More Articles| Formation of covalently closed circular DNA in Hep38.7-Tet cells, a tetracycline inducible hepatitis B virus expression cell line. Biochem. Biophys. Res. Commun. 452(3) , 315-21, (2014) Hepatitis B virus (HBV) covalently closed circular DNA (cccDNA) plays a central role in chronic HBV infection. However, analysis of the molecular mechanism of cccDNA formation is difficult because of ... | |
| Influence of the basal core promoter and precore mutation on replication of hepatitis B virus and antiviral susceptibility of different genotypes. J. Med. Virol. 87(4) , 601-8, (2015) Mutations in the basal core promoter (BCP) and precore (PC) regions of the hepatitis B virus (HBV) are more common in genotypes B and C than in genotype A, suggesting that these mutations might affect... | |
| Decreased liver distribution of entecavir is related to down-regulation of Oat2/Oct1 and up-regulation of Mrp1/2/3/5 in rat liver fibrosis. Eur. J. Pharm. Sci. 71 , 73-9, (2015) We aimed to elucidate whether entecavir was taken-up into liver by transporters and clarify the possible molecular mechanisms of changes in the distribution of entecavir in rat liver fibrosis.Thioacet... |
Synonyms
| 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one |
| entecavir (anhydrous) |
| 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)- |
| 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one |
| 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one |
| 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]- |
| Baraclude |
| entecavir |
| 9H-purin-6-ol, 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]- |
| UNII-NNU2O4609D |
| 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-9H-purin-6-ol |
