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Entecavir

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Identification
Molecular formula
C12H15N5O3
CAS number
209216-23-9
IUPAC name
(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
State
State

Entecavir is typically available in solid state, usually formulated into tablets for oral administration.

Melting point (Celsius)
220.30
Melting point (Kelvin)
493.50
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
277.28g/mol
Molar mass
277.2780g/mol
Density
1.7400g/cm3
Appearence

Entecavir appears as a white to off-white powder. It is a synthetic purine nucleoside analogue with selective activity against hepatitis B virus (HBV).

Comment on solubility

Solubility of (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

The solubility of the compound (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (C12H15N5O3) can be characterized as follows:

  • Aqueous Solubility: This compound exhibits moderate solubility in water due to the presence of multiple hydroxyl (-OH) groups, which can form hydrogen bonds with water molecules.
  • Solvent Compatibility: It is more soluble in polar solvents compared to non-polar solvents. Organic solvents such as methanol or dimethyl sulfoxide (DMSO) may enhance its solubility.
  • Influence of pH: The solubility may be influenced by the pH of the solution. Basic conditions could aid in protonation of the amino group, potentially increasing solubility.
  • Temperature Effects: Like many compounds, solubility may increase with temperature; hence, higher temperatures can lead to better dissolution.

In summary, the solubility of this compound is a result of its molecular structure, with key factors including solvent choice, temperature, and pH significantly impacting its solubility characteristics. Understanding these aspects is crucial for applications in medicinal chemistry and pharmaceutical formulations.

Interesting facts

Interesting Facts about (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

This complex organic compound, often studied in the realm of medicinal chemistry, is known for its intricate structure and potential biological activity. Below are some captivating insights about this compound:

  • Structural Complexity: The stereochemistry of this compound is significant as it contains multiple chiral centers, which can influence its interaction with biological systems.
  • Biological Implications: The presence of the 4-aminopyrrolo[2,3-d]pyrimidine moiety suggests potential applications in drug development, particularly as a scaffold for designing new therapeutics targeting various diseases.
  • Research Potential: This compound is of interest in pharmacological studies due to its potential to act on specific enzymes or receptors in the body, possibly contributing to the treatment of conditions like cancer or neurological disorders.
  • Hydroxymethyl Group: The unique hydroxymethyl group may enhance its solubility and biological activity, making it a subject of synthesis optimization in laboratories.
  • Importance of Stereochemistry: The specific configuration of the chiral centers plays a crucial role in biological assays; even slight changes in stereochemistry can lead to different pharmacodynamics.

In summary, this compound showcases the intricate dance between structure and function in the field of chemistry. As stated by renowned chemist Linus Pauling, "The best way to have a good idea is to have a lot of ideas." Thus, the exploration of compounds like this can lead to numerous innovative solutions in medicinal science!

Synonyms
tubercidin
7-Deazaadenosine
69-33-0
Sparsomycin A
Tubercidine
sparsamycin A
Antibiotic XK 101-1
SKI 26996
EINECS 200-703-4
UNII-M351LCX45Y
Adenosine, 7-deaza-
Antibiotic 155B2T
BRN 0038498
M351LCX45Y
U-10071
CHEBI:48267
AI3-52353
TUBERCIDIN [MI]
MFCD00056012
U10071
7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7-beta-D-ribofuranosyl-
CHEMBL267099
4-Amino-7-(beta-D-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine
4-Amino-7beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine
7-beta-D-Ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
7beta-D-Ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-4-amine
4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine
7-beta-D-Ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-4-amine
7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7beta-D-ribofuranosyl-
DTXSID701018946
NSC 56408
4-26-00-01117 (Beilstein Handbook Reference)
NSC-56408
(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
4-Amino-7-(b-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
7-beta-D-ribofuranosyl-7H-pyrrolo-(2,3-d)pyrimidin-4-amine
7-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Tubercidin Trifluoroacetate
U 10071
B 120121
4-Amino-7-(|A-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
Deazaadenosine
4-amino-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine
NSC56408
7-.BETA.-D-RIBOFURANOSYL-7H-PYRROLO(2,3-D)PYRIMIDIN-4-AMINE
2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
(2R,3R,4S,5R)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
4-Amino-7beta-D-ribofuranosyl-7H-pyrrolo(2, 3-d)pyrimidine
4-amino-7beta-D-ribofuranosyl-7H-pyrrolo[2, 3-d]pyrimidine
7-(beta-D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine
7H-Pyrrolo[2,3-d]pyrimidine, 4-amino-7-beta-D-ribofuranosyl-
Tubercidin?
7-BETA-D-RIBOFURANOSYL-7H-PYRROLO(2,3-D)PYRIMIDIN-4-AMINE
7 Deazaadenosine
(2R,3R,4S,5R)-2-(4-aminopyrrolo(2,3-d)pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
(2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo(2,3-d)pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
1pr5
7H-Pyrrolo(2,3-d)pyrimidin-4-amine, 7-beta-D-ribofuranosyl-
cid_6245
SCHEMBL8259
4-Amino-7-(.beta.-D-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine
MLS001074702
BIDD:GT0715
7-Deazaadenosine (Tubercidin)
7H-Pyrrolo(2,3-d)pyrimidine, 4-amino-7.beta.-D-ribofuranosyl-
GTPL4755
4-Amino-7 beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine
7-beta-CD-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidin-4-amine
DTXCID201476959
GLXC-04100
HMS2269L05
EX-A1062
BDBM50000298
AKOS024464517
CS-5578
DB03172
ND06290
NCGC00163638-01
(2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
AC-32279
BS-17423
SMR000471894
HY-100126
NS00011706
SR-01000765501
Tubercidin, from Streptomyces tubercidicus, ~95%
SR-01000765501-3
Q27089034
4-Amino-7-(?-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo(2, 3-d)pyrimidine
4-Amino-7.beta.-D-ribofuranosyl-7H-pyrrolo(2, 3-d)pyrimidine
4-Amino-7-.beta.-D-ribofuranosyl-7H-pyrrolo[2, 3-d]pyrimidine
7-beta-D-ribofuranosyl-7H-pyrrolo-(2,3-d)pyrimidin-4-amine (9CI)
7H-Pyrrolo[2,3-d]pyrimidine, 4-amino-7-.beta.-D-ribofuranosyl-
Tubercidin;4-Amino-7-b-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine;7-Deaza-D-adenosine
''2-(4-AMINO-PYRROLO[2,3-D]PYRIMIDIN-7-YL)-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-3,4-DIOL
(2R,3R,4S,5R)-2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (Tubercidin)
2-(4-Amino-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol(tubercidin)
200-703-4