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Zidovudine

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Identification
Molecular formula
C10H13N5O4
CAS number
30516-87-1
IUPAC name
(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid
State
State

At room temperature, zidovudine is in a solid state, typically available as a crystalline powder.

Melting point (Celsius)
123.00
Melting point (Kelvin)
396.15
Boiling point (Celsius)
263.00
Boiling point (Kelvin)
536.15
General information
Molecular weight
267.24g/mol
Molar mass
267.2410g/mol
Density
1.5700g/cm3
Appearence

Zidovudine appears as a white to off-white, odorless crystalline powder. It is freely soluble in water and soluble in alcohol and methanol.

Comment on solubility

Solubility of (2R,4S,5R,6R)-5-acetamido-2-[[[2R,3S,4R,5R]-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid

The solubility characteristics of this complex compound can be intriguing and are often determined by several factors, including its structural components and functional groups. Here are key points regarding its solubility:

  • Polarity: The presence of multiple hydroxyl (-OH) groups enhances its polarity, which generally favors solubility in polar solvents like water.
  • Hydrogen Bonding: The numerous hydrogen bond donors and acceptors in the molecule can lead to strong interactions with water molecules, facilitating solvation.
  • Amine Group: The amino group may also contribute to solubility through ionization, especially in acidic or basic solutions, increasing the compound's hydrophilicity.
  • Multi-functional Nature: With a plethora of functional groups such as acetamido, hydroxyl, and carboxylic acid groups, the compound is likely to have varied solubility across different pH ranges.
  • Insight from Structure: The tetrahydropyran and tetrahydrofuran rings might influence the compound's conformation and its interaction with solvents, potentially affecting solubility.

In summary, while predicting the solubility of such a multi-functional compound may not yield straightforward outcomes, its polar nature and ability to form hydrogen bonds suggest a relatively good solubility in aqueous solutions. As with many compounds, empirical testing is crucial to confirm these theoretical insights.

Interesting facts

Exploring (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)tetrahydropyran-2-carboxylic acid

This fascinating compound holds a significant place in medicinal chemistry due to its complex structure and versatile functionality. As a prodrug, it showcases the intricate interplay between structural modification and biological activity. Here are some intriguing aspects of this compound:

  • Structural Complexity: Its multi-ring structure and various functional groups, including hydroxyl, acetamido, and phosphoryl moieties, are emblematic of the compound's potential for diverse biological interactions.
  • Biological Relevance: This compound exhibits significant pharmacological properties, making it a candidate for therapeutic applications, particularly in the fields of antiviral and anticancer research.
  • Chirality: The presence of several chiral centers contributes to its enantioselectivity, which is crucial for optimal biological activity. The specific stereochemistry may influence the compound’s efficacy and safety profile.
  • Legacy in Research: Compounds of this class have guided numerous studies exploring metabolic pathways, enhancing our understanding of drug metabolism and mechanism of action.

As stated in the words of renowned chemist Linus Pauling, “The best way to have a good idea is to have lots of ideas.” This encapsulates the ongoing exploration of such compounds, where even subtle changes in structure can lead to groundbreaking advancements in pharmaceuticals. The journey of synthesizing and studying compounds like this underscores the creativity and innovation inherent in the field of chemistry.

Furthermore, the intricate design of this compound facilitates discussions on the importance of synthetic pathways and how they can be optimized for increased efficiency in drug development. Researchers continue to unravel its properties, striving to unlock new frontiers in therapeutic interventions.

Synonyms
Cmp-nana
CMP acetylneuraminic acid
(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CMP-N-acetylneuraminic acid
T8I6M8AXA0
UNII-T8I6M8AXA0
SCHEMBL23782673