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

ChemBase ID: 325
Molecular Formular: C12H15N5O3
Molecular Mass: 277.2792
Monoisotopic Mass: 277.11748937
SMILES and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one
IUPAC Traditional name
baraclude
Brand Name
Baraclude
Synonyms
entecavir
Entecavir
CAS Number
142217-69-4
PubChem SID
160963788
46504864
PubChem CID
153941

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.0033045  H Acceptors
H Donor LogD (pH = 5.5) -1.4469311 
LogD (pH = 7.4) -1.5362015  Log P -1.4446591 
Molar Refractivity 71.0008 cm3 Polarizability 26.432161 Å3
Polar Surface Area 125.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.81  LOG S -1.62 
Solubility (Water) 6.59e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Slightly soluble (2.4 mg/mL at pH 7.9, 25oC) expand Show data source
Hydrophobicity(logP)
-0.8 expand Show data source

DETAILS

DETAILS

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

REFERENCES

REFERENCES

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PATENTS

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