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Tenofovir disoproxil fumarate

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Identification
Molecular formula
C19H30N5O10P
CAS number
202138-50-9
IUPAC name
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate
State
State

Tenofovir disoproxil fumarate is typically in solid state at room temperature as a crystalline powder.

Melting point (Celsius)
115.00
Melting point (Kelvin)
388.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
273.15
General information
Molecular weight
635.52g/mol
Molar mass
635.5170g/mol
Density
1.4900g/cm3
Appearence

Tenofovir disoproxil fumarate appears as a white to off-white crystalline powder. It is soluble in methanol and slightly soluble in water.

Comment on solubility

Solubility of the Compound

The solubility characteristics of this complex compound featuring multiple functional groups can be quite intriguing. Here are some key points to consider:

  • Nature of the Functional Groups: The presence of hydroxyl (-OH) and amino (-NH2) groups often enhances solubility in polar solvents, such as water.
  • Salt Formation: Compounds with phosphoric acid moieties can readily interact with water, potentially forming soluble salts that increase overall solubility.
  • Conformation and Structure: The specific stereochemistry and three-dimensional arrangement of the compound may influence how well it can interact with solvent molecules.
  • Complex Interactions: Given the intricate design of the molecule, solubility may also be affected by its ability to form hydrogen bonds, engage in dipole-dipole interactions, and participate in hydrophobic effects.

In summary, while this compound is likely to exhibit some degree of solubility in polar solvents owing to its functional groups, the exact solubility profile may require empirical testing.
As with many biologically relevant compounds, understanding the kinetics of solubility and its implications in biological systems can be as important as the thermodynamic aspects of solubility.

Interesting facts

Interesting Facts about the Compound

This unique compound, characterized by its intricate structure, serves as a fascinating example of the complexity found in modern chemistry.

Structural Highlights

  • Chirality: The presence of multiple chiral centers in the molecule contributes to its potential for varied biological activity, making it a subject of interest in stereochemistry.
  • Functional Groups: This compound features numerous functional groups including amino, hydroxyl, and phosphate groups, which play critical roles in its reactivity and interactions with biological systems.
  • Phosphate Backbone: The phosphate groups are crucial as they facilitate energy transfer and storage, mimicking elements found in nucleic acids.

Biological Significance

The complexity and functional versatility of this compound may suggest potential roles in biochemistry:

  • Signal Transduction: Compounds with phosphono- groups are known to participate in signaling pathways, influencing cellular responses.
  • Drug Development: Given its unique structure, it may have implications in developing therapeutic agents targeting specific biological pathways.
  • Enzyme Inhibition: The presence of the aminopurine moiety might allow it to interact with enzymes, possibly acting as an inhibitor or modulator.

Research Applications

This compound is of great interest in research settings, particularly in:

  • Medicinal Chemistry: Understanding its interaction with biological systems could lead to innovative therapeutic strategies.
  • Biomolecular Studies: It serves as a model for studying nucleic acid structures and functions due to its polyfunctional nature.

In conclusion, this compound exemplifies the blend of complexity and functionality found in chemical substances, making it an intriguing subject for further study in both academic and practical fields. Its diverse applications highlight the ongoing importance of chemical research in understanding the molecular foundations of life.

Synonyms
85-61-0
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
900498-43-3
MFCD06795839
DTXSID9048302
Coenzyme A -SH
Coenzyme A, 250IU/mg
bmse000271
SCHEMBL26752
CHEMBL1623949
MFCD24368566
NS00100398
EN300-102292
F15115
Q407635
42747B78-0446-4B64-8D52-2C8B9B214EE7
(Z)-4-(((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-N-((Z)-3-hydroxy-3-((2-mercaptoethyl)imino)propyl)-3,3-dimethylbutanimidic acid