Entecavir

Structural formula
General
Non-proprietary name	Entecavir
other names	(1 S , 3 R , 4 S ) -2-Amino-1,9-dihydro-9- [4-hydroxy-3-hydroxymethyl-2-methylenecyclopentyl] -6 H -purin-6-one
Molecular formula	C 12 H 15 N 5 O 3
External identifiers / databases
CAS number 142217-69-4 (entecavir) 209216-23-9 (entecavir monohydrate) EC number 604-279-5 ECHA InfoCard 100.111.234 PubChem 153941 ChemSpider 135679 DrugBank DB00442 Wikidata Q418586
Drug information
ATC code	J05 AF10
Drug class	Antiviral
properties
Molar mass	277.28 g · mol -1
Melting point	> 220 ° C (entecavir monohydrate)
solubility	slightly soluble in water (2.4 mg ml −1 at 25 ° C)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Entecavir is a chemical analog of the nucleoside guanosine . It is an antiviral selected from the group of nucleoside reverse transcriptase inhibitors ( NRTI ) and is used as drug (trade name Baraclude ^® , Bristol-Myers Squibb ), for the treatment of hepatitis B used.

pharmacology

The nucleoside entecavir is phosphorylated to a nucleotide in the cell . Entecavir triphosphate is incorporated into the DNA in competition with the natural nucleotide deoxyguanosine triphosphate (dGTP). This leads to the inhibition of the viral reverse transcriptase :

• the primer formation by the HBV polymerase ,
• the reverse transcription of the negative DNA strand from the pregenomic mRNA ,
• the synthesis of the positive strand of HBV DNA.

literature

• Delaney, William E .; Yang, Huiling; Miller, Michael D .; Gibbs, Craig S .; Xiong, Shelly, Antimicrobial Agents and Chemotherapy , 3702-3710 (2004).
• Innaimo, SF et al., Antimicrob. Agents & Chemother., 1444-1448 (1997).
• Chang, T.-T. et al., N. Engl. J. Med. , 1001-1010 (2006).

Trade names

Entecavir is commercially available in Germany, Austria and Switzerland under the name Baraclude.

Individual evidence

1. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 613, ISBN 978-0-911910-00-1 .
2. ↑ Entecavir entry in the DrugBank of the University of Alberta , accessed November 28, 2018.
3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
4. ↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) , Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10 -9 , p. 180.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !