Skip to main content

Doxorubicin

ADVERTISEMENT
Identification
Molecular formula
C27H29N1O11
CAS number
23214-92-8
IUPAC name
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
State
State

At room temperature, doxorubicin is in a solid state, typically found as a crystalline powder due to its formulation for therapeutic use. Its physical form as a powder is practical for creating solutions for intravenous administration.

Melting point (Celsius)
208.00
Melting point (Kelvin)
481.15
Boiling point (Celsius)
380.00
Boiling point (Kelvin)
653.15
General information
Molecular weight
543.53g/mol
Molar mass
543.5250g/mol
Density
1.6000g/cm3
Appearence

Doxorubicin is a red-orange crystalline powder, often administered intravenously in a desolvated form in clinical settings. Its coloration is characteristic and can cause the urine of patients to appear red or pink due to rapid excretion through the urinary tract.

Comment on solubility

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

The solubility of complex compounds like (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione can be challenging to characterize due to their intricate structure and functional groups. However, several factors can provide insight into its solubility profile:

  • Polarity: The presence of multiple hydroxyl (-OH) groups and an amino (-NH2) group typically enhances solubility in polar solvents, particularly in water.
  • Hydrogen Bonding: Compounds that can form hydrogen bonds with solvent molecules tend to be more soluble. The hydroxyl and amino groups suggest a potential for significant interactions with water.
  • Hydrophobic Regions: The tetracene moiety, being largely hydrophobic, may hinder solubility in polar solvents, indicating a balance between hydrophilic and hydrophobic characteristics.
  • pH Dependence: The solubility may vary with pH, especially due to ionizable groups, which can affect the overall charge and interactions with solvents.

In general, one might expect:

  • Higher solubility in water due to numerous hydrophilic functionalities.
  • Lower solubility in non-polar solvents like hexane due to hydrophobic interactions.
  • Potential for increased solubility in organic solvents that can accommodate the hydrophobic tetracene structure alongside polar groups.

To gain a comprehensive understanding of its solubility, experimental data should be obtained to evaluate its behavior in various solvents.

Interesting facts

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

This complex organic compound is a fascinating example of the intricate chemistry found in natural products, often serving as a pivotal structure in various biological and chemical contexts. Here are some noteworthy aspects:

  • Natural Product Derivative: This compound is derived from the tetracene family, which is known for its unique properties and potential applications in organic electronics and photonic devices.
  • Biomedical Relevance: Its structural components, particularly the tetrahydropyran and methoxy groups, may impart biological activity, making it a candidate for research in pharmaceuticals, especially in areas related to antibacterial or anticancer agents.
  • Chirality and Stereochemistry: This compound showcases an intricate stereochemical arrangement. The specific configuration at multiple chiral centers can greatly influence its biological activity and interaction with biological macromolecules.
  • Hydroxyl Groups: The presence of hydroxyl groups in its structure aids in hydrogen bonding, potentially enhancing the compound's solubility and interaction with other molecules, which is essential for its activity.
  • Complex Synthetic Pathways: Due to its complex structure, synthesizing this compound requires advanced techniques in organic synthesis, including multiple steps of functional group transformation and stereoselective reactions, highlighting the skill level needed for chemists working with such compounds.

In summary, the study of (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione not only enriches our understanding of chemical synthesis but also opens new avenues for research in drug development and materials science. As highlighted by the saying, "The wonders of chemistry lie in the complexity and beauty of its structures."

Synonyms
daunorubicin
Daunomycin
20830-81-3
Acetyladriamycin
Leukaemomycin C
Rubidomycin
Daunorubicine
Daunarubicinum
Daunorrubicina
Daunamycin
(+)-Daunomycin
Rubomycin C
Daunorubicinum
Cerubidin
RP 13057
FI6339
Daunorubicina
FI 6339
FI-6339
ZS7284E0ZP
DTXSID7022883
RP-13057
CHEBI:41977
NCI-C04693
NSC-83142
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
(8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
DTXCID402883
NSC 82151
VYXEOS COMPONENT DAUNORUBICIN
Dauno-Rubidomycine
5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)-
5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
Dauno Rubidomycine
(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
daunomicina
(7S,9S)-9-acetyl-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
(8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
L01DB02
(8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
244-069-7
L-lyxo-Hexopyranoside, 3beta-acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-metldioxo-1a-naphthacenyl 3-amino-2,3,6-trideoxy-,alpha-
RefChem:919679
Cerubidine
DaunoXome
Daunorubicin (INN)
DaunoXome (TN)
5,12-Naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
MFCD00866340
NCGC00024246-05
Anthracycline
Anthracyline
DAUNORUBICIN [INN]
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Daunorubicinum [INN-Latin]
MLS000069508
Daunorubicin [INN:BAN]
RCRA waste no. U059
(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
(8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
CAS-20830-81-3
SMR000058559
CCRIS 914
SR-01000000033
SR-05000001600
HSDB 5095
EINECS 244-069-7
NSC 83142
VS-103
BRN 1445583
Tocris-1467
Daunorubicin(Daunomycin)
AI3-52942
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
Prestwick3_000487
DAUNOMYCIN [IARC]
DAUNORUBICIN [MI]
CHEMBL178
DAUNORUBICIN [HSDB]
SCHEMBL3041
DAUNORUBICIN [VANDF]
EPIRUBICIN IMPURITY D
UNII-ZS7284E0ZP
BSPBio_000353
DAUNORUBICIN [MART.]
cid_62770
orb611916
DAUNORUBICIN [WHO-DD]
BPBio1_000389
GTPL7063
SCHEMBL29354538
SCHEMBL29996035
BDBM32017
EX-A1337A
Valrubicin impurity, daunorubicin
Daunomycin;RP 13057;Rubidomycin
DAUNORUBICIN [ORANGE BOOK]
GLXC-23059
HMS2089H04
HMS2091K06
Pharmakon1600-01500223
Tox21_110896
BDBM50368352
GR-318
HY-13062A
LMPK13050002
NSC756717
Tox21_110896_1
CCG-212559
CS-2004
DB00694
MD32002
NSC-756717
NCGC00024246-06
NCGC00024246-07
NCGC00024246-09
NCGC00024246-10
NCGC00024246-12
NCGC00024246-15
NCGC00024246-18
NCGC00025173-01
(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside
(7S,9R)-9-Acetyl-7-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
SBI-0206677.P002
AB00514669
30D813
C01907
D07776
Epirubicin hydrochloride impurity, daunorubicin-
AB00514669-09
AB01644616_09
AB01644616_10
EN300-7479232
Q411659
SR-01000000033-4
SR-05000001600-1
SR-05000001600-2
BRD-K43389675-001-01-3
BRD-K43389675-001-02-1
BRD-K43389675-003-02-7
BRD-K43389675-003-03-5
BRD-K43389675-003-16-7
BRD-K43389675-003-20-9
EPIRUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]
VALRUBICIN IMPURITY, DAUNORUBICIN [USP IMPURITY]
DOXORUBICIN HYDROCHLORIDE IMPURITY A [EP IMPURITY]
EPIRUBICIN HYDROCHLORIDE IMPURITY, DAUNORUBICIN- [USP IMPURITY]
(1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-10-METHOXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSIDE
(7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-4-methoxy-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride
(7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
(8S,10S)-8-ACETYL-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-6,8,11-TRIHYDROXY-1-METHOXY-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE
(8S-cis)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro--6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
(8S-cis)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-n aphthacenedione;Daunomycin
5,12-NAPHTHACENEDIONE, 8-ACETYL-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL))OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-, (8S-CIS)-