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Doxorubicin

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Identification
Molecular formula
C27H29N1O11
CAS number
25316-40-9
IUPAC name
1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione
State
State

At room temperature, doxorubicin is typically found as a crystalline solid. It is commonly used in medical applications in the form of a hydrochloride salt which is soluble in water, facilitating its administration via injection.

Melting point (Celsius)
216.00
Melting point (Kelvin)
489.00
Boiling point (Celsius)
915.20
Boiling point (Kelvin)
1 188.40
General information
Molecular weight
543.53g/mol
Molar mass
543.5270g/mol
Density
1.6300g/cm3
Appearence

Doxorubicin appears as a red to orange-red crystalline powder. As a solution, it maintains its distinctive red color, which is characteristic for its use in injectable forms.

Comment on solubility

Solubility of 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione

The solubility of the compound 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione (C27H29N1O11) presents a complex profile due to its intricate molecular structure. Understanding the solubility can be broken down into several key points:

  • Polarity: The presence of multiple hydroxyl groups contributes to a heightened polarity, which often enhances solubility in polar solvents such as water.
  • Salt Formation: The inclusion of amine groups suggests potential for salt formation, which may improve solubility in aqueous solutions.
  • Hydrogen Bonding: The -OH and -NH groups can engage in hydrogen bonding, providing an additional pathway for solubility in various solvents.
  • Anticipated Behavior: Based on structural characteristics, one can hypothesize that this compound may be more soluble in ethanol or dimethyl sulfoxide (DMSO), which are polar aprotic solvents.

The solubility behavior can be summarized with the phrase: "Like dissolves like." Therefore, while this compound is likely soluble in polar solvents, its solubility in non-polar solvents will be significantly limited. Overall, the exploration of solubility for this compound is essential for its practical applications in diverse chemical environments.

Interesting facts

Interesting Facts About 1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione

The compound 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione, often referred to as a complex anthracene derivative, exhibits remarkable properties and applications in the field of chemistry and materials science. Here are some fascinating aspects of this compound:

  • Anthracene Core: This compound features an anthracene structure, which is known for its stability and ability to form strong π-π interactions, making it an excellent candidate for organic semiconductor applications.
  • Biological Significance: Compounds with similar structures are often studied for their potential use in medicinal chemistry, particularly regarding their behavior in biological systems and possible anti-cancer properties.
  • Functionalization: The presence of hydroxyl and amino groups enhances its solubility and reactivity, allowing for further modifications that can tune its chemical properties for specific applications.
  • Fluorescent Properties: Many anthracene derivatives exhibit fluorescence. This property can be leveraged in various applications, such as in sensors, light-emitting devices, and biological imaging.
  • Multi-Activity: The compound is a part of a larger class of polycyclic aromatic compounds that can exhibit multiple activities, including anti-bacterial and anti-fungal, contributing to ongoing research in pharmaceutical development.

In summary, 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione stands out not only for its complex structure but also for its diverse applications in science and technology. A notable quote related to such compounds is: "In every molecule, there lies a story waiting to be unraveled." This compound represents the intersection of chemistry, biology, and materials science, opening doors to exciting research opportunities.

Synonyms
mitoxantrone
65271-80-9
Mitozantrone
Mitoxanthrone
Mitoxantron
Mitoxantrona
DHAQ
Mitoxantronum
Misostol
Mitoxantrone [INN]
Mitoxantronum [INN-Latin]
Mitoxantrona [INN-Spanish]
CCRIS 7604
NSC 279836
NSC-279836
UNII-BZ114NVM5P
DHAD
BZ114NVM5P
NSC279836
1,4-Bis(2-(2-hydroxyethylamino)ethyl)amino)-5,8-dihydroxyanthraquinone
1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione
BRN 2795126
Mitoxantrone (INN)
Mitoxantrone free base
CHEBI:50729
5,8-Bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxyanthraquinone
1,4-Dihydroxy-5,8-bis(2-((2-hydroxyethyl)amino)ethylamino)-9,10-anthracenedione
1,4-Dihydroxy-5,8-bis(5-hydroxy-3-azapentylamino)anthrachinon
1,4-dihydroxy-5,8-bis[2-[(1,1,2,2-tetradeuterio-2-hydroxyethyl)amino]ethylamino]anthracene-9,10-dione
1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dione
1,4-DIHYDROXY-5,8-BIS({2-[(2-HYDROXYETHYL)AMINO]ETHYL}AMINO)-9,10-ANTHRACENEDIONE
9,10-Anthracenedione, 1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-
MLS002703044
DTXSID4046947
65271-80-9 (free base)
MFCD00242942
1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione
ANTHRAQUINONE, 5,8-BIS((2-((2-HYDROXYETHYL)AMINO)ETHYL)AMINO)-1,4-DIHYDROXY-
NSC299195
NSC301739
MITOXANTRONE (IARC)
MITOXANTRONE [IARC]
Mitoxantronum (INN-Latin)
Mitoxantrona (INN-Spanish)
1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione
1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione
MIX
MLS001333711
9,10-Anthracenedione, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-
Misostol (TN)
NCGC00015693-02
Mitoxantrone (free base)
SMR000058480
Mitoxantrone [INN:BAN]
CAS-70476-82-3
DHAQ (*Diacetate salt*)
SR-01000076001
Mitoxantrone base
2fum
1,4-DIHYDROXY-5,8-BIS((2-((2-HYDROXYETHYL)AMINO)ETHYL)AMINO)-9,10-ANTHRACENEDIONE
1,4-dihydroxy-5,8-bis(2-(2-hydroxyethylamino)ethylamino)anthracene-9,10-dione
1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]anthracene-9,10-dione
Immunex (Salt/Mix)
dihydroxyanthracenedione
Spectrum_001655
Mitoxantrone (Standard)
CHEMBL58
Prestwick0_000385
Prestwick1_000385
Prestwick2_000385
Prestwick3_000385
Spectrum2_000908
Spectrum3_001590
Spectrum4_000866
Spectrum5_001205
Lopac-M-6545
MITOXANTRONE [MI]
cid_4212
Neuro_000153
SCHEMBL3000
MITOXANTRONE [VANDF]
BIDD:PXR0181
Lopac0_000779
BSPBio_000569
BSPBio_003160
KBioGR_001531
KBioSS_002135
DivK1c_000516
MITOXANTRONE [WHO-DD]
SPBio_000756
SPBio_002490
BPBio1_000627
GTPL7242
DTXCID2026947
BDBM67690
cid_5458171
KBio1_000516
KBio2_002135
KBio2_004703
KBio2_007271
KBio3_002660
L01DB07
NINDS_000516
GLXC-03038
HMS2090D05
HMS3655E20
KUC108634N
BCP02861
CCG-36371
HY-13502R
s1889
STK631833
Mitoxantrone hydrochloride (Salt/Mix)
AKOS005564036
BCP9000931
DB01204
FD26022
KSC-19-204
SDCCGSBI-0050757.P004
IDI1_000516
SMP2_000179
NCGC00015693-01
NCGC00015693-03
NCGC00015693-04
NCGC00015693-05
NCGC00015693-06
NCGC00015693-08
NCGC00015693-13
NCGC00015693-23
NCGC00162251-01
AC-37649
AS-35321
HY-13502
MITOXANTRONE, Mitoxantrone Hydrochloride, Mitoxantrone dihydrochloride, MITOXANTHRONE HYDROCHLORIDE
NCI60_002276
NCI60_002535
SMR001549953
SY226320
SBI-0050757.P003
AB00053716
M3133
NS00008439
SW196745-6
VU0244399-2
D08224
EN300-117257
AB00053716-18
AB00053716-19
AB00053716-22
AB00053716_23
AB00053716_24
Q239426
SR-01000076001-7
BRD-K21680192-001-01-5
BRD-K21680192-001-11-4
BRD-K21680192-300-05-2
BRD-K21680192-300-07-8
BRD-K21680192-300-09-4
BRD-K21680192-300-10-2
BRD-K21680192-300-12-8
BRD-K21680192-300-14-4
BRD-K21680192-300-15-1
BRD-K21680192-300-16-9
1,4-bis[2-(2-hydroxyethylamino)-ethylamino]-5,8-dihydroxyanthraquinone
1,4-bis[2-(2-hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone
1,4-dihydroxy-5,8-bis[[2-(2-hydroxyethylamino)ethyl]amino]anthraquinone
9, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl] amino]-
1,3-Dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-9, 10-anthracenedione
1,4-Dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-9, 10-anthroquinone
1,4-Dihydroxy-5,8-bis-[[2-[(2-hydroxyethyl)amino]ethyl]amino]anthraquinone
1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]-9,10-anthraquinone;hydrochloride
1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione;hydrochloride
1,4-bis[2-(2-hydroxyethylamino)ethylamino]-5,8-bis(oxidanyl)anthracene-9,10-dione;hydrochloride
1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]-anthracene-9,10-dione;DHAQ;NSC-279836
MITOXANTRONE; 1,4-DIHYDROXY-5,8-BIS({2-[(2-HYDROXYETHYL)AMINO]ETHYL}AMINO)ANTHRA-9,10-QUINONE