Skip to main content

Entecavir

ADVERTISEMENT
Identification
Molecular formula
C12H15N5O3F
CAS number
209216-23-9
IUPAC name
(2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
State
State

At room temperature, Entecavir is a solid. It is stable under normal temperatures and pressures and remains in its powder form unless processed further into a pharmaceutical preparation.

Melting point (Celsius)
220.00
Melting point (Kelvin)
493.15
Boiling point (Celsius)
265.00
Boiling point (Kelvin)
538.15
General information
Molecular weight
295.27g/mol
Molar mass
295.2710g/mol
Density
1.8880g/cm3
Appearence

Entecavir is a white to off-white crystalline powder. It is often used in its hydrate form, which has no distinct odor, and is visually similar to many other pharmaceutical-grade powders.

Comment on solubility

Solubility of (2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

This fascinating compound, often referred to as a modified nucleoside, exhibits notable solubility characteristics that are essential for its functional applications. The solubility of this compound can be influenced by various factors such as:

  • Polarity: Given the presence of hydroxymethyl and amino groups, the compound is likely to be polar, enhancing its solubility in polar solvents such as water.
  • Hydrogen Bonding: The formation of hydrogen bonds with surrounding solvent molecules can significantly increase solubility. These functional groups participate in strong hydrogen bonding interactions.
  • pH Sensitivity: The solubility can also be pH-dependent, particularly for molecules containing amine functionalities, which may become protonated under acidic conditions, potentially increasing solubility.

In laboratory settings, it is crucial to consider these properties, as they dictate how the compound behaves in various solutions. For example, quotes like "like dissolves like" highlight the relationship between the solvent and the solute regarding their polarity. Thus, when investigating solutions containing this compound, one can expect it to show favorable solubility in aqueous environments compared to non-polar solvents.

In summary, the solubility of (2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol is fundamentally influenced by its molecular structure, intermolecular interactions, and external conditions.

Interesting facts

Interesting Facts About (2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

This fascinating compound boasts a complex structure that showcases the intricate relationships between carbohydrates and nucleobases. Here are some key points that highlight its significance:

  • Biological Relevance: This molecule is a derivative of purine, an essential component of nucleic acids (DNA and RNA). Its structure allows it to participate in various biochemical pathways, especially in nucleotide metabolism.
  • Fluorinated Features: The presence of a fluorine atom in the structure indicates that this compound may possess unique pharmacological properties compared to its non-fluorinated counterparts. Fluorination often enhances the metabolic stability and bioactivity of compounds.
  • Potential Therapeutic Applications: Given its composition, this compound could serve as a valuable scaffold in drug design, particularly in anticancer or antiviral therapies, where nucleoside analogs are critical.
  • Stereochemistry: The specification of stereocenters (2R, 3R, 4S, 5R) indicates the compound's chirality, which plays a crucial role in its biological activity. The spatial arrangement of atoms can dramatically influence how this compound interacts with biological targets.
  • Research Tool: Compounds like this one are often used in scientific studies to better understand metabolic pathways and cellular processes involving nucleic acids.

Overall, (2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol is a remarkable compound that epitomizes the blend of chemistry and biology. As scientists unravel its potential applications, it stands as a testament to how a single molecule can have extensive implications in health and medicine.

Synonyms
2-Fluoroadenosine
146-78-1
ADENOSINE, 2-FLUORO-
(2R,3R,4S,5R)-2-(6-Amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
2-Fas
6-Amino-2-fluoro-9-beta-D-ribofuranosylpurine
SRI 727
NSC 30605
UNII-0S67290CRJ
2-(6-AMINO-2-FLUORO-PURIN-9-YL)-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-3,4-DIOL
BRN 0043956
2-Far
Purine, 6-amino-2-fluoro-9-beta-D-ribofuranosyl-
CHEBI:39740
AI3-52599
0S67290CRJ
MFCD00866394
(2R,3R,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CHEMBL290077
DTXSID70163252
4-26-00-03723 (Beilstein Handbook Reference)
NSC-30605
2-FLUORO-9-.BETA.-D-RIBOFURANOSYLADENINE
Purine, 6-amino-2-fluoro-9-.beta.-D-ribofuranosyl-
2FA
2-Fluoro-9-beta-D-ribofuranosyladenine; NSC 30605;
2-FluoroAdo
NCGC00181336-01
2-fluoroade-nosine
2-Fluoroadenosine, 97%
cid_8975
MLS001066367
SCHEMBL977919
DTXCID0085743
HMS2231E03
BDBM50118807
PDSP1_001071
PDSP2_001055
AKOS015853307
AKOS015920272
BCP9000107
DB04441
NF08852
(2R,3R,4S,5R)-2-(6-amino-2-fluoro-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
NCGC00181336-02
AC-22363
BP-58636
DS-15294
PD016313
SMR000471849
BCP0726000182
NS00069546
2-FLUORO-9-BETA-D-RIBOFURANOSYLADENINE
6-Amino-2-fluoro-9-(b-D-ribofuranosyl)purine
EN300-7361945
BRD-K72238567-001-12-4
Q27095228
Z2065671281
(2R,3R,4S,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
633-923-8