CAS Number142217-69-4
Synonyms2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one; entecavir (anhydrous); 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one; Baraclude; entecavir; UNII-NNU2O4609D; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-9H-purin-6-ol
Molecular FormulaC12H15N5O3
Molecular Weight295.29
Purity97%
Density1.8±0.1 g/cm3
Boiling Point734.2ºC at 760 mmHg
Melting Point249-252ºC
AppearanceWhite to off-white/yellow crystalline powder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 142217-69-4 |
| Catalog No. | 2A-9090343 |
| Chinese Name | 恩替卡韦 |
| Synonyms | 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one; entecavir (anhydrous); 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one; Baraclude; entecavir; UNII-NNU2O4609D; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-9H-purin-6-ol |
| Molecular Formula | C12H15N5O3 |
| Molecular Weight | 295.29 |
| Purity | 97 |
| Density | 1.8±0.1 g/cm3 |
| Boiling Point | 734.2ºC at 760 mmHg |
| Melting Point | 249-252ºC |
| Appearance | White to off-white/yellow crystalline powder |
| Storage Condition | -20°C Freezer |
| Application | Entecavir (SQ 34676; BMS 200475) is a selective and effective HBV inhibitor. The EC50 value in HepG2 cells is 3.75 nM. |
| HTC | 2933990090 |
| PubChem ID | 641041 |
| SMILES | C=C1C(CO)C(O)CC1n1cnc2c(=O)[nH]c(N)nc21 |
| InChI | 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 |
| InChI Key | QDGZDCVAUDNJFG-FXQIFTODSA-N |
| Bioactivity | 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 >> HBV Research 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 |
| Use of | Properties Articles18 Name entecavir (anhydrous) Synonym More Synonyms Entecavir Biological Activity Related Catalog Signaling Pathways >> Anti-infection >> HBV Research Areas >> Infection 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]. 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 Molecular Formula C12H15N5O3 Exact Mass 277.117493 PSA 130.05000 LogP -0.96 Index of Refraction 1.837 InChIKey QDGZDCVAUDNJFG-FXQIFTODSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: 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% |
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