| Identification | Back Directory | [Name]
ADRIAMYCINONE | [CAS]
24385-10-2 | [Synonyms]
Ccris 7633
ADRIAMYCINONE
Doxorubicinone
adriamycinaglycone
Epirubicin aglycon
Epirubicin aglycone
Doxorubicin aglycone
8-glycoloyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-Naphthacenedione
(8S,10S)-7,8,9,10-Tetrahydro-6,8,10,11-tetrahydroxy 8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
7,8,9,10-Tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxy acetyl)-1-methoxy-(8S-cis)-5,12-naphthacenedione
5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)- | [Molecular Formula]
C21H18O9 | [MDL Number]
MFCD00871832 | [MOL File]
24385-10-2.mol | [Molecular Weight]
414.36 |
| Chemical Properties | Back Directory | [Appearance]
Red Solid | [Melting point ]
223-225°C | [Boiling point ]
741.2±60.0 °C(Predicted) | [density ]
1.671±0.06 g/cm3(Predicted) | [storage temp. ]
Amber Vial, -20°C Freezer | [solubility ]
Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
7.45±0.60(Predicted) | [color ]
Red to Very Dark Red | [Stability:]
Light Sensitive | [InChI]
InChI=1S/C21H18O9/c1-30-11-4-2-3-8-14(11)20(28)16-15(17(8)25)18(26)9-5-21(29,12(24)7-22)6-10(23)13(9)19(16)27/h2-4,10,22-23,26-27,29H,5-7H2,1H3/t10-,21-/m0/s1 | [InChIKey]
IBZGBXXTIGCACK-CWKPULSASA-N | [SMILES]
C1(OC)=C2C(C(=O)C3=C(C2=O)C(O)=C2C(C[C@@](O)(C(CO)=O)C[C@@H]2O)=C3O)=CC=C1 | [CAS DataBase Reference]
24385-10-2 |
| Hazard Information | Back Directory | [Chemical Properties]
Red Solid | [Uses]
A metabolite of Doxorubicin (Dx). | [Description]
Doxorubicinone is a metabolite of the anthracycline antitumor antibiotic doxorubicin . Doxorubicinone inhibits mitochondrial succinoxidase from bovine heart and reduces the mitochondrial inner membrane potential in rat heart and liver mitochondria in a concentration-dependent manner. Doxorubicinone (40 μM) increases pentose phosphate pathway flux by 45% and reduces activity of glutathione peroxidase (GPx) and superoxide dismutase (SOD) by 17 and 60%, respectively, in human erythrocytes. It also induces cytotoxicity in patient-derived ovarian cancer colonies in a concentration-dependent manner. | [Definition]
ChEBI: Adriamycinone is a member of tetracenes and a quinone. | [General Description]
ADRIAMYCINONE (ADR-ONE) is an aglycone. It is a metabolite of adriamycin converted in the body, and another metabolite is amycinol (ADR-OL)[1]. Adriamycin nephropathy (AN) is a rodent model of chronic kidney disease. AN is characterized by podocyte injury followed by glomerulosclerosis, tubulointerstitial inflammation and fibrosis. | [storage]
Store at -20°C | [References]
[1] Emara S, et al. Effect of cyclodextrins on the stability of adriamycin,
adriamycinol, adriamycinone and daunomycin. Talanta, 2008; 51: 359-364. |
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