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Budesonide

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Identification
Molecular formula
C25H34O6
CAS number
51333-22-3
IUPAC name
(2S,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13,17-pentamethyl-3-oxo-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-2-carbonitrile
State
State

At room temperature, budesonide is typically encountered as a solid. It is formulated into various dosages by pharmaceutical companies, often in the form of inhalers or nasal sprays, due to its poor solubility in water and bioavailability challenges.

Melting point (Celsius)
224.00
Melting point (Kelvin)
497.15
Boiling point (Celsius)
547.50
Boiling point (Kelvin)
820.65
General information
Molecular weight
430.53g/mol
Molar mass
430.5330g/mol
Density
1.2800g/cm3
Appearence

Budesonide appears as a white to off-white powder. It is commonly used in its micronized form for pharmaceutical formulations where precise dosing is required. This fine powder form ensures greater surface area and consistency in products such as inhalers and nasal sprays.

Comment on solubility

Solubility of (2S,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13,17-pentamethyl-3-oxo-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-2-carbonitrile

The solubility of this complex organic compound is an intriguing subject due to its unique structural characteristics. Here are some key considerations regarding its solubility profile:

  • Polarity: The presence of hydroxyl (-OH) and cyano (-CN) groups tends to enhance polarity, which can lead to increased solubility in polar solvents like water.
  • Hydrophobicity: Conversely, the considerable hydrophobic hydrocarbon structure may limit solubility in aqueous environments, making it more soluble in non-polar solvents such as hexane or chloroform.
  • Temperature Dependence: Solubility can also be influenced by temperature - generally, solubility increases with temperature for solid compounds.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvent molecules may improve the solubility in polar solvents. For instance, water can solvate the hydroxyl group effectively.

It is essential to carry out empirical solubility tests to determine its exact solubility characteristics, as theoretical predictions can sometimes diverge from practical observations. In summary, the solubility of this compound is dictated by a balance of its polar and non-polar characteristics, and interactions with potential solvents play a pivotal role in solubility behavior.

Interesting facts

Interesting Facts about (2S,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13,17-pentamethyl-3-oxo-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-2-carbonitrile

This compound is an intriguing example of a complex organic molecule with significant implications in various fields of research, especially in medicinal chemistry. Here are some fascinating points to consider:

  • Steroid-like Structure: The molecular structure of this compound reveals a steroid-like framework, which is essential for its biological activity. The specific stereochemistry (noted by the configuration labels) plays a crucial role in determining how it interacts with biological systems.
  • Biological Relevance: Such compounds can often mimic or block the action of hormones in the body, making them valuable in the design of pharmaceuticals, especially in treating conditions related to hormone levels.
  • Challenges in Synthesis: The complexity in the synthesis of this compound is notable. The multiple chiral centers make it a challenging target for synthetic chemists, necessitating advanced techniques and methodologies to achieve the desired stereochemistry.
  • Potential Therapeutic Applications: Research suggests that compounds with similar structures could be explored for their potential as anti-cancer agents or in regulating metabolic pathways, making them significant in drug discovery.
  • Interesting Nomenclature: The long and complex name reflects the detailed and intricate nature of the molecule. Each component of the name corresponds to specific functional groups and structural features of the compound, providing chemists with essential information about its structure at a glance.

In summary, this compound not only exemplifies the rich complexity found in organic chemistry but also highlights the potential avenues for innovative medicinal applications. As researchers continue to explore compounds like this, we can anticipate exciting developments in the field of drug design and biochemical research.

Synonyms
Cyanoketone
Cyanotrimethylandrostenolone
4248-66-2
BRN 5763422
2alpha-Cyano-4,4,17alpha-trimethyl-3-oxo-5-androstene-17beta-ol
2alpha-Cyano-4,4,17alpha-trimethylandrost-5-en-17beta-ol-3-one
2-alpha-Cyano-4,4,17-alpha-trimethylandrost-5-en-17-beta-ol-3-one
2alpha-Cyano-4,4,17alpha-trimethyl-17beta-hydroxy androst-5-ene-3-one
ANDROST-5-ENE-2-alpha-CARBONITRILE, 17-beta-HYDROXY-4,4,17-TRIMETHYL-3-OXO-
Androst-5-ene-2-carbonitrile, 17-hydroxy-4,4,17-trimethyl-3-oxo-, (2alpha,17beta)-
EPG65S4XCZ
UNII-EPG65S4XCZ
(2S,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13,17-pentamethyl-3-oxo-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-2-carbonitrile
SCHEMBL18925
DTXSID50962528
Androst-5-ene-2-carbonitrile, 17-hydroxy-4,4,17-trimethyl-3-oxo-, (2.alpha.,17.beta.)-
Q5197469
2alpha-Cyano-4,4,17-trimethyl-17beta-hydroxy-5-androsten-3-one
17beta-Hydroxy-4,4,17-trimethyl-3-oxoandrost-5-ene-2alpha-carbonitrile
Androst-5-ene-2alpha-carbonitrile, 17beta-hydroxy-4,4,17-trimethyl-3-oxo-
(2alpha,17beta)-17-Hydroxy-4,4,17-trimethyl-3-oxoandrost-5-ene-2-carbonitrile