Doxorubicinol

Names

[ Name ]:
Doxorubicinol

[Synonym ]:
14-hydroxydaunomycinone
adriamycinaglycone
8-glycoloyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-Naphthacenedione
doxorubicin aglycone
Doxorubicinol
Adriamycin-aglycon
(1S,3S)-3-[(1S)-1,2-Dihydroxyethyl]-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
Epirubicin aglycone
doxorubicin hydroxyaglycone
5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
Epirubicin aglycon
Doxorubicinone
13-dihydrodoxorubicin

Biological Activity

[Description]:

Doxorubicinol, a potent inhibitor of the cardiac sarcoplasmic reticulum calcium pump, inhibits systolic myocardial function in isolated heart muscle. Doxorubicinol inhibits tumor cell growth and has cardiotoxicity.

[Related Catalog]:

Research Areas >> Cardiovascular Disease

[In Vitro]

Doxorubicinol 抑制分离的乳头肌的舒张功能（即增加静息压）[1]。 Doxorubicinol 在显著降低舒张功能的浓度下，阿霉素几乎完全消除钙泵活性[1]。 Doxorubicinol 抑制 Ca2+ 刺激的骨骼肌肌浆网的 ATP 酶活性，并消除犬和兔心脏制备物中肌膜的 Na+/K+-ATP 酶活性[1]。 Doxorubicinol 抑制 PANC-1 细胞的增殖，IC50 值为 35.4 μM，PD PaCa 细胞的 IC50 值为 44.5 μM，WD PaCa 细胞的 IC50 值为 49.5 μM[1]。

[References]

[1]. Olson RD, et al. Doxorubicin cardiotoxicity may be caused by its metabolite, doxorubicinol. Proc Natl Acad Sci U S A. 1988 May;85(10):3585-9.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
828.7±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₃₁NO₁₁

[ Molecular Weight ]:
545.54

[ Flash Point ]:
455.0±34.3 °C

[ Exact Mass ]:
545.189697

[ PSA ]:
209.23000

[ LogP ]:
2.01

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.717

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QI9326000

CHEMICAL NAME :: 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-10-((3-amino-2,3,6-trideoxy-alpha -L-lyxo- hexopyranosyl)oxy)-8-(1,2-dihdyroxyethyl)-1-methoxy-6 ,8,11-trihydroxy-, (8S-(8-alpha,8(R*), 10-alpha))-

CAS REGISTRY NUMBER :: 54193-28-1

LAST UPDATED :: 199706

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C27-H31-N-O11

MOLECULAR WEIGHT :: 545.59

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 26900 nmol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 41,1006,1981

Precursor & DownStream

Precursor

DownStream

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.