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Entecavir

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Identification
Molecular formula
C12H15N5O3
CAS number
142217-69-4
IUPAC name
(2R,3R,4S,5R)-2-[(8R)-8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
State
State

Entecavir is typically in a solid state at room temperature. It presents as a crystalline powder that is white to off-white in color.

Melting point (Celsius)
220.00
Melting point (Kelvin)
493.15
Boiling point (Celsius)
401.00
Boiling point (Kelvin)
674.15
General information
Molecular weight
278.30g/mol
Molar mass
278.3020g/mol
Density
1.7900g/cm3
Appearence

Entecavir is a white to off-white crystalline powder. It is sparingly soluble in water.

Comment on solubility

Solubility Overview

The compound (2R,3R,4S,5R)-2-[(8R)-8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol presents interesting considerations regarding its solubility characteristics. Evaluating the solubility of this complex structure is essential for understanding its potential applications.

Factors Influencing Solubility

  • Polarity: Given the presence of multiple hydroxyl groups in the structure, which enhance hydrogen bonding, the compound is likely to be more soluble in polar solvents.
  • Hydrogen Bonding: The imidazo and tetrahydrofuran moieties contribute to possible hydrogen bonding interactions, which can further affect solubility.
  • Steric Hindrance: The spatial arrangement of substituents can create steric hindrance that may impact the extent to which the compound interacts with solvents.

Solvent Compatibility

The solubility of this compound is expected to vary significantly between solvents. It may exhibit the following trends:

  • High solubility in water: Due to the numerous –OH functional groups, the compound can interact favorably with water molecules.
  • Low solubility in non-polar solvents: Compounds with substantial polar character tend to have limited solubility in organic solvents like hexane or toluene.

In conclusion, the solubility of (2R,3R,4S,5R)-2-[(8R)-8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol showcases the intricate balance of chemical structure and solvent interactions, emphasizing the importance of *solvent selection* in any practical application.

Interesting facts

Interesting Facts about (2R,3R,4S,5R)-2-[(8R)-8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

This compound is a fascinating example of a complex structure that incorporates multiple functional groups and stereocenters, granting it unique properties and potential applications in medicinal chemistry. Here are some intriguing facts about this compound:

Structural Intricacies

  • The presence of multiple stereogenic centers makes this compound a chiral molecule, meaning it can exist in different configurations that may exhibit varying biological activities.
  • The inclusion of an imidazodiazepine moiety is notable; these structures are often found in several pharmaceutical agents, particularly those targeting the central nervous system.

Biological Significance

  • Compounds with imidazole components often exhibit biological activities such as antiviral, antibacterial, and antifungal properties.
  • Given its structural complexity, this compound could potentially serve as a lead structure for developing new therapeutic agents, especially in the treatment of neurological disorders.

Potential Applications

  • Researchers are exploring similar imidazodiazepine derivatives as anxiolytics and sedatives, showcasing their possible application in the realm of mental health.
  • The tetrahydrofuran ring contributes to solubility and bioavailability, important factors when considering drug formulation.

This compound exemplifies the intricate relationships between chemical structure and biological activity, underscoring the importance of detailed structural analysis in drug development. As science progresses, the exploration of such compounds may unlock new therapeutic avenues and improve existing treatments.

Synonyms
coformycin
11033-22-0
UNII-E49510ZL0H
(R)-3,4,7,8-Tetrahydro-3-beta-D-ribofuranosylimidazo(4,5-d)(1,3)diazepin-8-ol
CHEBI:16213
E49510ZL0H
Imidazo(4,5-d)(1,3)diazepin-8-ol, 3,4,7,8-tetrahydro-3-beta-D-ribofuranosyl-, (R)-
NSC-277817
(8R)-3-beta-D-ribofuranosyl-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
(2R,3R,4S,5R)-2-[(8R)-8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)oxolane-3,4-diol
NSC 277817
IMIDAZO(4,5-D)(1,3)DIAZEPIN-8-OL, 3,4,7,8-TETRAHYDRO-3-.BETA.-D-RIBOFURANOSYL-, (8R)-
(8R)-3-beta-D-ribofuranosyl-3,6,7,8-tetrahydroimidazo(4,5-d)(1,3)diazepin-8-ol
(2R,3R,4S,5R)-2-((8R)-8-hydroxy-7,8-dihydro-4H-imidazo(4,5-d)(1,3)diazepin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol
(R)-3,4,7,8-Tetrahydro-3-b-D-ribofuranosylimidazo(4,5-D)(1,3)diazepin-8-ol
(R)-3,4,7,8-Tetrahydro-3-I2-D-ribofuranosylimidazo(4,5-D)(1,3)diazepin-8-ol
IMIDAZO(4,5-D)(1,3)DIAZEPIN-8-OL, 3,4,7,8-TETRAHYDRO-3-BETA-D-RIBOFURANOSYL-, (8R)-
CHEMBL284483
NSC277817
SCHEMBL442534
YOOVTUPUBVHMPG-LODYRLCVSA-N
BDBM50367032
AKOS040745679
DA-64416
HY-117260
CS-0064597
C01677
Q27098587
Imidazo[4,5-d][1,3]diazepin-8-ol, 3,4,7,8-tetrahydro-3-.beta.-D-ribofuranosyl-, (8R)
Imidazo[4,5-d][1,3]diazepin-8-ol,3,4,7,8-tetrahydro-3-b-D-ribofuranosyl-, (8R)-
(2R,3R,4S,5R)-2-[(8R)-8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol