Entecavir A guanine analog that inhibits reverse transcription

Entecavir (CAS 142217-69-4)

Entecavir | CAS 142217-69-4 is rated 5.0 out of 5 by 1.
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Synonym: 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one
Application: A guanine analog that inhibits reverse transcription
CAS Number: 142217-69-4
Purity: ≥99%
Molecular Weight: 277.28
Molecular Formula: C12H15N5O3
* Refer to Certificate of Analysis for lot specific data (including water content).
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Entecavir is a deoxyguanosine nucleoside analogue with antiviral activity against the hepatitis B virus (HBV). The compound has a mechanism of action by inhibiting priming and chain extension through inhibition of HBV DNA polymerase. Entecavir is also documented as the most potent HBV DNA polymerase inhibitor and superior to Lamivudine (sc-221830) due to its effectiveness against Lamivudine resistant HBV strains and being 30 fold more active.


References

1. Thomas, H., et al. 2003. J. Hepatol. 39: S93-S98. PMID: 14708685
2. Rivkin, A. 2007. Drugs Today. 43: 201-220. PMID: 17460784

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in water (2.2-3 mg/ml), DMSO, and methanol.
Storage :
Store at room temperature
Melting Point :
238-244° C
Boiling Point :
661.40° C at 760 mmHg (Predicted)
Density :
1.81 g/cm3 (Predicted)
Refractive Index :
n20D 1.84 (Predicted)
Optical Activity :
α20/D +36.8°, c = 0.1 in methanol
IC50 :
Human immunodeficiency virus: EC5050 = 0.1 nM; Hepatitis B virus: EC5050 = 2.4 nM; HepG2: EC5050 = 3 nM (human); HIV-1: EC5050 = 9 µM (MT-2); HIV-PSEUDOTYPED NL4-3: EC5050 = 12.6 µM (HEK-293)
pK Values :
pKa: 9.64 (Predicted), pKb: 2.64 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
UP0789600
PubChem CID :
153941
MDL Number :
MFCD00907887
Beilstein Registry :
7692760
SMILES :
C=C1[C@H](C[C@@H]([C@H]1CO)O)N2C=NC3=C2NC(=NC3=O)N

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Certificate of Analysis

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Entecavir  Product Citations

See how others have used Entecavir. Click on the entry to view the PubMed entry .

Citations 1 to 5 of 5 total

PMID: # 26779022  Mandíková, J. et al. 2015. Frontiers in pharmacology. 6: 304.

PMID: # 25550158  Tsukuda, S. et al. 2015. J. Biol. Chem. 290: 5673-84.

PMID: # 24126184  Vlčková, H. et al. 2014. J Pharm Biomed Anal. 88: 337-44.

PMID: # 24025329  Watashi, K. et al. 2013. J. Biol. Chem. 288: 31715-27.

PMID: # 22520634  Nováková, L. et al. 2012. J Chromatogr A. 1259: 237-43.

Citations 1 to 5 of 5 total
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Rated 5 out of 5 by from Geipel Geipel, A. et al. (PubMed 25560463) reported that the antiviral Entecavir allows an unexpectedly high residual replication of HBV mutants resistant to lamivudine. -SCBT Publication Review
Date published: 2015-05-10
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