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

Doxorubicinol

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Precursor & DownStream

Precursor

DownStream

Related Compounds