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Doxorubicin

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Identification
Molecular formula
C27H29N3O11
CAS number
23214-92-8
IUPAC name
[(7R,8S)-5-acetyl-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
State
State

At room temperature, doxorubicin is typically supplied as a hydrochloride salt which is a crystalline powder. It is not usually described as having a liquid or gaseous form for most practical purposes in pharmaceutical use.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.15
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
543.53g/mol
Molar mass
543.5250g/mol
Density
1.5900g/cm3
Appearence

Doxorubicin hydrochloride appears as a red-orange, crystalline solid. It is usually available in a powdered form which is used to make up solutions for injection. The vibrant color is due to its chromophore system, which is typical of anthracycline antibiotics.

Comment on solubility

Solubility of [(7R,8S)-5-acetyl-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

The solubility of a compound can significantly influence its behavior in various chemical processes. In the case of [(7R,8S)-5-acetyl-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate, several factors come into play:

  • Polarity: The presence of functional groups, such as carbamates and amino groups, generally enhances solubility in polar solvents, particularly water.
  • Hydrogen bonding: The ability to form hydrogen bonds with water molecules can lead to increased solubility.
  • Overall structure: The intricate structure of the compound, characterized by multiple rings and substituents, can hinder solubility in certain solvents.

It is important to note that solubility can be represented by Martindale's rule which states that “like dissolves like”. In this case, the compound is more likely to dissolve in solvents that mimic its polar characteristics, such as:

  • Dimethyl sulfoxide (DMSO)
  • Water
  • Ethanol

Conversely, nonpolar solvents such as hexane or aromatic hydrocarbons may prove less effective for dissolving this compound due to its polar nature. Understanding these solubility characteristics not only aids in predicting the compound's behavior in various environments but also assists in its practical applications in chemical research and medicine.

Interesting facts

Interesting Facts About [(7R,8S)-5-acetyl-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate

This compound is a fascinating example of complex organic chemistry. Its unique structure and properties make it a subject of extensive research. Here are some notable aspects:

  • Complex Structure: The compound belongs to a class known as tetracyclic frameworks, which is characterized by its intricate multi-ring system. The specific arrangement of its rings contributes to its unique chemical behavior.
  • Biological Relevance: Many compounds with similar structural characteristics have been found to exhibit significant biological activity, including antimicrobial and anti-inflammatory effects. This opens avenues for medicinal chemistry.
  • Synthetic Challenges: The synthesis of such complex molecules can be incredibly challenging. Chemists often employ creative strategies like protecting groups and stereoselective reactions to achieve the desired compound efficiently.
  • Potential Applications: Due to its various functional groups, this compound shows potential as a lead compound in drug discovery, particularly targeting specific biological pathways.

As a chemist, one might emphasize the importance of exploring similar complex compounds, stating, "Understanding the nuances of such intricate structures broadens our scope of discovering life-saving drugs." This compound exemplifies how the intersection of chemistry and biology can usher in innovation in pharmaceuticals.

Due to the ongoing research and the implications this compound holds, it is crucial to study its reactivity and interaction with biological systems in greater detail to unlock its full potential.

Synonyms
(1-Acetyl-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl hydrogen carbonimidate
DTXSID70911533
[(7R,8S)-5-Acetyl-11-amino-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate