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Tenofovir

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Identification
Molecular formula
C9H14FN5O4
CAS number
147127-20-6
IUPAC name
[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
State
State

At room temperature, Tenofovir appears as a stable solid and is mainly available in its fumarate form for increased solubility and bioavailability when used in medication.

Melting point (Celsius)
118.00
Melting point (Kelvin)
391.00
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.00
General information
Molecular weight
287.22g/mol
Molar mass
287.2180g/mol
Density
2.1000g/cm3
Appearence

Tenofovir disoproxil is usually observed as a white to off-white crystalline powder, which is practically insoluble in water. Its appearance may vary slightly depending on the crystalline form or formulation.

Comment on solubility

Solubility of [(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate

The solubility of the compound [(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate can be attributed to several key factors that influence its behavior in different solvents:

  • Structural Characteristics: The presence of functional groups such as the dihydrogen phosphate and fluorinated pyrimidine enhances its interaction with polar solvents, leading to increased solubility in water.
  • Polarity: This compound's significant polarity, due to the phosphate group and hydroxy functionalities, suggests a tendency to dissolve well in polar solvents like water.
  • Hydrogen Bonding: The hydroxy and phosphate groups can engage in hydrogen bonding, which aids in solubility under optimal conditions.
  • Temperature Dependence: As with many compounds, solubility may increase with temperature, facilitating greater interaction with the solvent molecules.
  • pH Sensitivity: Given that this is a phosphate compound, its solubility could be influenced by the pH of the solution; an acidic medium could enhance solubility, while neutral or alkaline conditions could lead to precipitation.

In summary, the solubility of this complex compound is primarily characterized by its polar nature, the potential for hydrogen bonding, and responsiveness to environmental conditions such as temperature and pH. Such features make it a compound of interest for various applications in fields requiring solubility modulation.

Interesting facts

Interesting Facts about [(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate

This complex compound is a fascinating example of how organic chemistry can bridge pharmaceuticals and biochemistry. Its design showcases intricate stereochemistry with specific chiral centers that play a crucial role in its biological activity.

Key Features:

  • Fluorinated Pyrimidine: The presence of a fluorine atom in the structure enhances the metabolic stability and lipophilicity, making it more effective in biological systems.
  • Phosphate Group: The dihydrogen phosphate part of the molecule is pivotal in bioenergetics and cellular signaling, often acting as a substrate in enzymatic processes.
  • Stereochemical Configuration: The (2R,3S,5R) stereocenters indicate that this molecule can have specific interactions with biological receptors, potentially leading to unique pharmacological properties.

Researchers are particularly drawn to this compound due to its potential implications in drug design. Its structural properties could allow it to mimic naturally occurring compounds, thus enhancing its biological efficacy. As noted by a prominent chemist, "The integration of various functional groups within a single molecule can lead to unexpected synergies and improved therapeutic outcomes."

Applications:

  • Potential use in the development of antiviral or anticancer agents.
  • Exploration in enzyme inhibition due to its phosphate moiety.
  • Studied for its ability to modulate biological pathways through its interaction with nucleic acids.

In conclusion, the multifaceted structure of this compound not only underlines the beauty of chemistry but also underscores its significant potential in the pharmaceutical landscape. The ongoing research in this area continues to reveal how slight modifications in molecular design can have profound implications for human health.

Synonyms
5-fluoro-2'-deoxyuridine-5'-monophosphate
134-46-3
5-fluorodeoxyuridine monophosphate
FdUMP
FLUORODEOXYURIDYLATE
5FdUMP
F-dUMP
5-Fluoro-dUMP
[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
88410-68-8
CHEMBL886
2'-deoxy-5-fluorouridine 5'-(dihydrogen phosphate)
5'-Uridylic acid, 2'-deoxy-5-fluoro-
CHEBI:2129
5 Fluoro 2' Deoxyuridine 5' Monophosphate
DTXSID60158450
7CJ707H131
[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
2'-Deoxy-5-fluoro-5'-uridylic Acid Ammonium Salt
5-FLUORO-2-DEOXYURIDINE MONOPHOSPHATE (FDUMP)
5-Fluoro-2'-deoxyuridine 5'-Monophosphate Ammonium Salt (up to 20% 3'-monophosphate)
UFP
((2R,3S,5R)-5-(5-fluoro-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl)methyl dihydrogen phosphate
FOSIFLOXURIDINE
DB03761
SCHEMBL6107
DTXCID6080941
UNII-7CJ707H131
5-FLUORO-2'-DEOXY-UMP
BDBM50022238
CAS 134-46-3
PD059482
5-Fluoro-2'-deoxy-5'-monophosphateuridine
DB-225175
NS00069545
5-FLUORO-2'-DEOXYURIDINE 5'-PHOSPHATE
C04242
F90253
5-FLUORO-2''-DEOXYURIDINE-5''-MONOPHOSPHATE
Q27105559
URIDINE, 2'-DEOXY-5-FLUORO-, 5'-(DIHYDROGEN PHOSPHATE)
(R)-5-Fluoro-1-((4S,5R)-4-hydroxy-5-methylphosphate-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
2 inverted exclamation mark -Deoxy-5-Fluorouridine 5 inverted exclamation mark -phosphate triethylammonium
Phosphoric acid mono-[(2R,3S,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester
Phosphoric acid mono-[5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester