CHEMICAL AND PHYSICAL PROPERTIES
Physical Description | Solid |
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Color/Form | White to off white powder |
Solubility | Slightly soluble (2.4 mg/mL at pH 7.9, 25 °C) |
LogP | -0.8 |
pH | pH = 7.9 in a saturated solution of water at 25 °C |
Other Experimental Properties | White to off-white powder, mp: >220 °C. Specific optical rotation: +35 deg at 25 °C/D (c = 0.38 in water). Solubility in water: 2.4 mg/mL. pH of saturated solution in water is 7.9 at 25 °C /Entecavir monohydrate/ |
COMPUTED DESCRIPTORS
Molecular Weight | 277.28 g/mol |
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XLogP3 | -1.3 |
Hydrogen Bond Donor Count | 4 |
Hydrogen Bond Acceptor Count | 5 |
Rotatable Bond Count | 2 |
Exact Mass | 277.11748936 g/mol |
Monoisotopic Mass | 277.11748936 g/mol |
Topological Polar Surface Area | 126 Ų |
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 |
PRODUCT INTRODUCTION
description
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 EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor and an antiviral drug. It is a member of 2-aminopurines, an oxopurine, a primary alcohol and a secondary alcohol.