Entecavir

CAT: 0013-GTR19163259-02Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0013-GTR19163259-02Size:5 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 Number	142217-69-4
PubChem CID	135398508
IUPAC Name	2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
Molecular Formula	C12H15N5O3
Molecular Weight	277.28
XLogP	-1.3
Topological Polar Surface Area	126
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Heavy Atom Count	20
Formal Charge	0
Complexity	480

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

CAS: 142217-69-4

CID: 135398508

Formula: C12H15N5O3

MW: 277.28

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	277.28
XLogP3	-1.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	277.11748936
Monoisotopic Mass	277.11748936
Topological Polar Surface Area	126 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	480
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
BA1816-100	Entecavir

Entecavir

Chemical Information

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