Doxorubicinone
Synonym(s):(8S,10S)-6,8,10,11-Tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione;(8S,10S)-7,8,9,10-Tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione;Adriamycin aglycone;Adriamycinone;Doxorubicin aglycone
- CAS NO.：24385-10-2
- Empirical Formula: C21H18O9
- Molecular Weight: 414.36
- MDL number: MFCD00871832
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-02-02 21:55:19
What is Doxorubicinone?
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.
Chemical properties
Red Solid
The Uses of Doxorubicinone
A metabolite of Doxorubicin (Dx).
What are the applications of Application
Doxorubicinone is a metabolite of Doxorubicin (Dx)
Definition
ChEBI: Adriamycinone is a member of tetracenes and a quinone.
General Description
Doxorubicinone (adriamycinone) is an aglycone. It is a metabolite of adriamycin converted in the body, and another metabolite is amycinol [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.
References
[1] Emara S, et al. Effect of cyclodextrins on the stability of adriamycin, adriamycinol, adriamycinone and daunomycin. Talanta, 2008; 51: 359-364.
Properties of Doxorubicinone
| 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 |
| CAS DataBase Reference | 24385-10-2 |
Safety information for Doxorubicinone
Computed Descriptors for Doxorubicinone
| 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 |
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![[14-14C]DOXORUBICIN HYDROCHLORIDE](https://img.chemicalbook.in/StructureFile/ChemBookStructure4/GIF/CB5420582.gif)
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