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Entecavir

CAS No.
142217-69-4
Chemical Name:
Entecavir
Synonyms
Etv;Baraclude;entikawei;2-amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one;CS-863;CS-1236;Entecavi;SQ 34676;Enticavir;ENTECAVIR
CBNumber:
CB0506719
Molecular Formula:
C12H15N5O3
Molecular Weight:
277.28
MDL Number:
MFCD00907887
MOL File:
142217-69-4.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

Entecavir Properties

Melting point 249-252°C
Boiling point 661.4±65.0 °C(Predicted)
Density 1.81±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility DMSO (Slightly), Methanol (Sparingly)
form powder
pka 14.22±0.60(Predicted)
color white to beige
optical activity [α]/D +25 to +40°, c = 0.2 in H2O
Stability Hygroscopic
CAS DataBase Reference 142217-69-4(CAS DataBase Reference)
FDA UNII NNU2O4609D
NCI Drug Dictionary Baraclude
ATC code J05AF10

Pharmacokinetic data

Protein binding 13%
Excreted unchanged in urine 75%
Volume of distribution Large
Biological half-life 128-149 / -

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H320-H335
Precautionary statements  P264-P270-P301+P312-P330
Safety Statements  24/25
WGK Germany  3
HS Code  29339900

Entecavir price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML1103 Entecavir ≥98% (HPLC) 142217-69-4 10MG $61 2023-06-20 Buy
Sigma-Aldrich SML1103 Entecavir ≥98% (HPLC) 142217-69-4 50MG $247 2023-06-20 Buy
Tocris 6234 Entecavir ≥98%(HPLC) 142217-69-4 10 $50 2021-12-16 Buy
Tocris 6234 Entecavir ≥98%(HPLC) 142217-69-4 50 $198 2021-12-16 Buy
TRC E558900 Entecavir 142217-69-4 250mg $130 2021-12-16 Buy
Product number Packaging Price Buy
SML1103 10MG $61 Buy
SML1103 50MG $247 Buy
6234 10 $50 Buy
6234 50 $198 Buy
E558900 250mg $130 Buy

Entecavir Chemical Properties,Uses,Production

Pharmacodynamics

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.

Description

Entecavir is a cyclopentyl guanosine analog launched for the once-daily oral treatment of chronic hepatitis B virus (HBV) infection, and it is the third nucleoside or nucleotide analog to be marketed for this indication. Lamivudine, a deoxythiacytosine analog, and adefovir dipivoxil, a nucleotide analog, have been marketed since 1998 and 2002, respectively. Entecavir and adefovir are specifically indicated for HBV, whereas lamivudine is indicated for both HBV and HIV infections.

Chemical Properties

White to Off-White/Yellow Crystalline Powder

Originator

BMS (US)

Uses

Entecavir is a new generation of guanine nucleoside analogues oral medicine for treatment of hepatitis B virus infection in, mainly for the treatment of adult patients with viral replication activity and serum transaminase continued to increase, or liver tissue for pathological activity of chronic hepatitis B, is currently down virus the fastest and the most powerful, the mutation rate lowest nucleoside analogues.

Definition

ChEBI: 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 ha no activity against HIV. It is used for the treatment of chronic hepatitis B.

Trade name

Baraclude (BMS)

Mechanism of action

Entecavir is a nucleoside analog, or more specifically, a deoxyguanosine analogue that belongs to a class of carbocyclic nucleosides and inhibits reverse transcription, DNA replication and transcription in the viral replication process.

Pharmacokinetics

Entecavir had a mean terminal half-life ranging from 128 to 149 hours and an effective half-life of approximately 24 hours. Elimination was predominantly through renal excretion, with mean urinary recovery ranging from 62% to 73%.

Clinical Use

Treatment of chronic hepatitis B virus infection in patients >16 years of age.
Entecavir comes as a tablet and solution (liquid) to take by mouth. It is usually taken once a day on an empty stomach, at least 2 hours after a meal and at least 2 hours before the next meal. Take entecavir at around the same time every day.

Side effects

The most common side effects of entecavir: the increase of ALT, fatigue, dizziness, nausea, abdominal pain, abdominal discomfort, abdominal discomfort, liver, muscle, insomnia, rubella and indigestion, also be found in neutrophils decreased slightly.
These adverse reactions were mild to moderate. It also found that, as the same type of antiviral drugs, entecavir and the first generation of antiviral drugs have similar side effects, such as acid poisoning, hepatomegaly, liver fatty degeneration in the withdrawal will appear rebound phenomenon.

Synthesis

Entecavir is synthesized from 4-trimethylsilyl-3-butyn-2-one and acrolein. The key features of its preparation are: (1) a stereoselective boron–aldol reaction to afford the acyclic carbon skeleton of the methylenecylopentane moiety; (2) its cyclization by a Cp2TiCl-catalyzed intramolecular radical addition of an epoxide to an alkyne; and (3) the coupling with a purine derivative by a Mitsunobu reaction.142217-69-4.png

storage

Store at -20°C

1383812-22-3
142217-69-4
Synthesis of Entecavir from Cyclopentanemethanol, 5-(acetyloxy)-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylene-, 1-acetate, (1R,3S,5S)-
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View Lastest Price from Entecavir manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Entecavir pictures 2024-11-22 Entecavir
142217-69-4
US $0.00-0.00 / g 1g 99% HPLC 1000kg HangZhou RunYan Pharma Technology Co.,LTD.
Entecavir pictures 2024-11-22 Entecavir
142217-69-4
US $0.00 / g 1g 99%min 1000g WUHAN FORTUNA CHEMICAL CO., LTD
Entecavir pictures 2024-11-22 Entecavir
142217-69-4
US $0.00 / Kg/Bag 2Kg/Bag 96% up 20 tons Sinoway Industrial co., ltd.
  • Entecavir pictures
  • Entecavir
    142217-69-4
  • US $0.00-0.00 / g
  • 99% HPLC
  • HangZhou RunYan Pharma Technology Co.,LTD.
  • Entecavir pictures
  • Entecavir
    142217-69-4
  • US $0.00 / g
  • 99%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Entecavir pictures
  • Entecavir
    142217-69-4
  • US $0.00 / Kg/Bag
  • 96% up
  • Sinoway Industrial co., ltd.
Aids098045 Aids-098045 Enticavir EntikaweiPian 2-Amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-3H-purin-6(9H)-one ,99.7% (1S,3R,4S)-9-[4-Hydroxy-3-(hydroxyMethyl)-2-Methylenecyclopentyl]guanine Entecavir Anhydrous 20MG/100MG/100G Entecavir Tablets Entecavir (as hydrate) Entecavir,99%e.e. Entecavi ENTECAVIR, 98-102% entecavir Baraclude 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylidene-cyclopentyl]-3H-purin-6-one, Baraclude ENTECAVIR 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylidene-cyclopentyl]-3H-purin-6-one SQ 34676 6-H-Purin-6-one-,2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl] Entecavir USP Impurity B 2-amino-9-[(1R,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-3H-purin-6-one hydrate CS-863 CS-1236 Entecavir, BMS200475 Entecavir(SQ 34676 Entecavir/Entecavir Monohydrate Entecavir USP/EP/BP 2-Amino-9-(4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl)-3,9-dihydro-purin-6-one Etv 2-amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one Baraclude entikawei 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylene-cyclopentyl]-1H-purin-6-one 142217-69-4 209216-23-6 12477-69-4 The latest anti hepatitis b anti-aids drugs Anti-virals Heterocycles API Nucleotides and Nucleosides Bases & Related Reagents Intermediates & Fine Chemicals Nucleotides Pharmaceuticals Inhibitors Antiviral Agents 142217-69-4