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Entecavir

CAT: 0013-GTR19163259-08Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19163259-08Size:500 mg
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Description
Entecavir (BMS200475; SQ34676) is a guanosine analogue that inhibits reverse transcription, DNA replication and transcription in the viral replication process; oral antiHBV drug. (In Vitro) :BMS-200475 has a EC50 of 3.75 nM against HBV. It is incorporated into the protein primer of HBV and subsequently inhibits the priming step of the reverse transcriptase. The antiviral activity of BMS-200475 is significantly less against the other RNA and DNA viruses. Entecavir is more readily phosphorylated to its active metabolites than other deoxyguanosine analogs (penciclovir, ganciclovir, lobucavir, and aciclovir) or lamivudine. The intracellular half-life of entecavir is 15 h. (In Vivo) :Daily oral treatment with BMS-200475 at doses ranging from 0.02 to 0.5 mg/kg of body weight for 1 to 3 months effectively reduces the level of woodchuck hepatitis virus (WHV) viremia in chronically infected woodchucks.
CAS Number
142217-69-4
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO: 10 mM
Smiles
C=C1[C@H] (C[C@@H] ([C@H]1CO) O) N2C=NC3=C2NC (=NC3=O) N
Molecular Formula
C12H15N5O3
Molecular Weight
277.28
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

Entecavir

Entecavir (anhydrous) is 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 has no activity against HIV. It is used for the treatment of chronic hepatitis B. It has a role as an antiviral drug and an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor. It is a primary alcohol, a member of 2-aminopurines, an oxopurine and a secondary alcohol.

CAS Number142217-69-4
PubChem CID135398508
IUPAC Name2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
Molecular FormulaC12H15N5O3
Molecular Weight277.28
XLogP-1.3
Topological Polar Surface Area126
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Heavy Atom Count20
Formal Charge0
Complexity480
SMILES
C=C1[C@H](C[C@@H]([C@H]1CO)O)N2C=NC3=C2N=C(NC3=O)N
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
Chemical Structure
2D Structure
2D structure of Entecavir
CAS: 142217-69-4
CID: 135398508
Formula: C12H15N5O3
MW: 277.28
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight277.28
XLogP3-1.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass277.11748936
Monoisotopic Mass277.11748936
Topological Polar Surface Area126 Ų
Heavy Atom Count20
Formal Charge0
Complexity480
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BA1816-100Entecavir

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