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Doxorubicin Hydrochloride

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Identification
Molecular formula
C27H29NO11·HCl
CAS number
25316-40-9
IUPAC name
(7S,9S)-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
State
State

At room temperature, Doxorubicin Hydrochloride is typically a solid in its pure form. It is commonly used in the pharmaceutical industry and prepared as an injectable solution for therapeutic use.

Melting point (Celsius)
209.00
Melting point (Kelvin)
482.00
Boiling point (Celsius)
514.00
Boiling point (Kelvin)
787.00
General information
Molecular weight
579.99g/mol
Molar mass
579.9850g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin Hydrochloride usually appears as a red-orange powder. It is often supplied in a lyophilized form, which is reconstituted before administration in medical settings. The compound is sensitive to light and should be stored away from direct sunlight to maintain its stability.

Comment on solubility

Solubility of (7S,9S)-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; hydrochloride

The solubility of (7S,9S)-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; hydrochloride is an important characteristic that influences its application and functionality in various fields.

The following factors greatly affect the solubility of this compound:

  • Polarity: The presence of hydroxyl (-OH) groups and amino (-NH2) groups often enhances the compound's solubility in polar solvents, such as water.
  • Hydrochloride Form: Being a hydrochloride salt typically improves the solubility of the base compound in water due to the ionization that occurs in aqueous solution.
  • Structural Complexity: The intricate structure, which includes multiple functional groups, may lead to variable solubility in different solvents based on their interactions.

In general, compounds like this one may exhibit:

  • High solubility in water due to the presence of polar functional groups.
  • Possible solubility in organic solvents depending on the specific interactions with solvent molecules.

It's essential to consult empirical data or perform specific solubility tests to determine the exact solubility profile, as the solubility can vary significantly based on temperature and pH.

Understanding solubility not only assists in optimizing formulations but also in predicting the bioavailability and overall behavior of the compound in biological systems.

Interesting facts

Interesting Facts about (7S,9S)-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; hydrochloride

This complex organic compound has been of great interest in pharmaceutical chemistry due to its intricate structure and potential biological applications. Here are some fascinating aspects:

  • Bioactivity: The compound exhibits promising biological activities, particularly in the fields of antimicrobial and anti-inflammatory research. Its specific substitutions play crucial roles in enhancing its biological properties.
  • Synthesis Complexity: The synthesis of this compound involves multiple reaction steps, showcasing the artistry of organic synthesis. The introduction of the tetrahydropyran moiety is particularly noteworthy as it adds complexity to the overall structure.
  • Structure-Activity Relationship: Studying the structure-activity relationship leads to a better understanding of how slight changes in the molecular structure can significantly affect biological activity. Researchers focus on how different functional groups influence the effectiveness of the compound.
  • Potential Applications: Beyond its possible therapeutic uses, this compound could serve as a model for developing new drugs, especially in the realm of antibiotic resistance. As scientists combat microbial resistance, compounds like this may provide essential insights.
  • Chirality and Selectivity: The (7S,9S) configuration indicates that chirality plays a critical role in its behavior in biological systems, often leading to variations in activity between enantiomers.

As a chemist or a student, studying such a compound enhances your appreciation for the intricacies of organic chemistry and its implications in the real world. With ongoing research, who knows what new applications might be discovered for this fascinating compound?

Synonyms
Adriblastin
ADM hydrochloride
FI 6804
4'-epi-Adriamycin hydrochloride
MLS002702107
DOX HCl
Ellence (Pharmacia)
Pidorubicin hydrochloride
ADR
Adriamycin PFS (Pharmacia)
SCHEMBL317302
CHEMBL543353
SCHEMBL29464047
Doxorubicin HCl Liposome Injection
NSC848498
CCG-208148
CCG-208196
NSC-848498
D4193
(7S,9S)-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
5, 10-[(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride
5, 10-[(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S-cis)-
5, 10-[(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S-cis)-
L-lyxo-Hexopyranoside,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1a-naphthacenyl 3-amino-2,3,6-trideoxy-, .alpha.-, hydrochloride