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142217-69-4 分子结构
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2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one

ChemBase编号:325
分子式:C12H15N5O3
平均质量:277.2792
单一同位素质量:277.11748937
SMILES和InChIs

SMILES:
O[C@@H]1[C@H](C(=C)[C@@H](n2c3[nH]c(nc(=O)c3nc2)N)C1)CO
Canonical SMILES:
OC[C@@H]1[C@@H](O)C[C@@H](C1=C)n1cnc2c1[nH]c(N)nc2=O
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
InChIKey:
QDGZDCVAUDNJFG-FXQIFTODSA-N

引用这个纪录

CBID:325 http://www.chembase.cn/molecule-325.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one
IUPAC传统名
baraclude
商标名
Baraclude
别名
entecavir
Entecavir
CAS号
142217-69-4
PubChem SID
160963788
46504864
PubChem CID
153941

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00442 external link
PubChem 153941 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 8.0033045  质子受体
质子供体 LogD (pH = 5.5) -1.4469311 
LogD (pH = 7.4) -1.5362015  Log P -1.4446591 
摩尔折射率 71.0008 cm3 极化性 26.432161 Å3
极化表面积 125.76 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -0.81  LOG S -1.62 
溶解度 6.59e+00 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
Slightly soluble (2.4 mg/mL at pH 7.9, 25oC) expand 查看数据来源
疏水性(logP)
-0.8 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00442 external link
Item Information
Drug Groups approved; investigational
Description 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.
Indication For the treatment of chronic hepatitis B virus infection in adults with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease.
Pharmacology Entecavir is a guanosine nucleoside analogue with selective activity against hepatitis B virus (HBV). It is designed to selectively inhibit the Hepatitis B virus, blocking all three steps in the replication process. Entecavir is more efficient than an older Hepatitis B drug, lamivudine.
Toxicity Healthy subjects who received single entecavir doses up to 40 mg or multiple doses up to 20 mg/day for up to 14 days had no increase in or unexpected adverse events. If overdose occurs, the patient must be monitored for evidence of toxicity, and standard supportive treatment applied as necessary.
Affected Organisms
Hepatitis B virus
Biotransformation Entecavir is not a substrate, inhibitor, or inducer of the cytochrome P450 (CYP450) enzyme system. Entecavir is efficiently phosphorylated to the active triphosphate form.
Absorption Absorption Following oral administration in healthy subjects, entecavir peak plasma concentrations occurred between 0.5 and 1.5 hours. In healthy subjects, the bioavailability of the tablet is 100% relative to the oral solution.
Half Life After reaching peak concentration, entecavir plasma concentrations decreased in a bi-exponential manner with a terminal elimination half-life of approximately 128-149 hours. The phosphorylated metabolite has a half-life of 15 hours.
Protein Binding Binding of entecavir to human serum proteins in vitro is approximately 13%.
Clearance * renal cl=383.2 +/- 101.8 mL/min [Unimpaired renal function]
* renal cl=197.9 +/- 78.1 mL/min [Mild impaired renal function]
* renal cl=135.6 +/- 31.6 mL/min [Moderate impaired renal function]
* renal cl=40.3 +/- 10.1 mL/min [severe impaired renal function]
* apparent oral cl=588.1 +/- 153.7 mL/min [Unimpaired renal function]
* apparent oral cl=309.2 +/- 62.6 mL/min [Mild impaired renal function]
* apparent oral cl=226.3 +/- 60.1 mL/min [Moderate impaired renal function]
* apparent oral cl=100.6 +/- 29.1 mL/min [severe impaired renal function]
* apparent oral cl=50.6 +/- 16.5 mL/min [severe impaired renal function amnaged with Hemodialysis]
* apparent oral cl=35.7 +/- 19.6 mL/min [severe impaired renal function amnaged with CAPD]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

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专利

专利

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