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SML1103

Sigma-Aldrich

Entecavir

≥98% (HPLC)

Synonym(s):

2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one, 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-3,9-dihydro-purin-6-one, BMS 200475, SQ 34,676

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About This Item

Empirical Formula (Hill Notation):
C12H15N5O3
CAS Number:
142217-69-4
Molecular Weight:
277.28
MDL number:
MFCD11046562
UNSPSC Code:
51111800
PubChem Substance ID:
329825478
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +25 to +40°, c = 0.2 in H2O

storage condition

desiccated

color

white to beige

solubility

H2O: 0.5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

O=C1C2=C(N([C@H]3C[C@H](O)[C@@H](CO)C3=C)C=N2)NC(N)=N1

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

InChI key

QDGZDCVAUDNJFG-FXQIFTODSA-N

Biochem/physiol Actions

Entecavir is an antiviral guanine analog that inhibits reverse transcription, DNA replication and transcription in the viral replication process. Entecavir is used to treat hepatitis B.
Entecavir is used as an effective drug to treat lamivudine-refractory patients with chronic hepatitis B virus (CHB) at a dose of 1 mg daily.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Philip Rosenthal et al.
Hepatology (Baltimore, Md.), 69(6), 2326-2337 (2018-10-16)
The optimal management strategy for children with immune-tolerant chronic hepatitis B virus (HBV) infection remains unknown. The purpose of this clinical trial was to determine the safety and efficacy of therapy with entecavir and peginterferon in a group of children
Amir Shlomai et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(33), 12193-12198 (2014-08-06)
Hepatitis B virus (HBV) chronically infects 400 million people worldwide and is a leading driver of end-stage liver disease and liver cancer. Research into the biology and treatment of HBV requires an in vitro cell-culture system that supports the infection
Masashi Iwamoto et al.
Scientific reports, 7(1), 10620-10620 (2017-09-08)
Viruses exploit host factors and environment for their efficient replication. The virus-host interaction mechanisms for achieving an optimal hepatitis B virus (HBV) replication have been largely unknown. Here, a single cell cloning revealed that HepAD38 cells, a widely-used HBV-inducible cell
Michiyo Hayakawa et al.
Scientific reports, 10(1), 47-47 (2020-01-09)
Nucleos(t)ide analog (NA) therapy has proven effective in treating chronic hepatitis B. However, NAs frequently result in viral relapse after the cessation of therapy. This is because NAs cannot fully eliminate the viral episomal covalently closed circular DNA (cccDNA) in
Chia-Chi Wang et al.
Journal of the Formosan Medical Association = Taiwan yi zhi, 113(11), 786-793 (2013-08-06)
Several anti-viral drugs are approved for the treatment of hepatitis B virus (HBV) infection. However, whether quantitative hepatitis B surface antigen (qHBsAg) can predict the therapeutic response during long-term entecavir treatment remains unclear. Fifty-five chronic hepatitis B (CHB) patients who
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