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Doxorubicinone

Doxorubicinone Structure
CAS No.
24385-10-2
Chemical Name:
Doxorubicinone
Synonyms
Ccris 7633;ADRIAMYCINONE;Doxorubicinone;Epirubicin aglycon;adriamycinaglycone;Epirubicin aglycone;Doxorubicin aglycone;Doxorubicinone-13C-D3;D2-N-Nitroso desmethyldoxycycline;Doxorubicin Hydrochloride EP Impurity D
CBNumber:
CB2121622
Molecular Formula:
C21H18O9
Molecular Weight:
414.36
MOL File:
24385-10-2.mol
MSDS File:
SDS
Modify Date:
2024/2/2 21:55:19

Doxorubicinone Properties

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

SAFETY

Risk and Safety Statements

Doxorubicinone Chemical Properties,Uses,Production

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

Uses

A metabolite of Doxorubicin (Dx).

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.

Doxorubicinone Preparation Products And Raw materials

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Epirubicin aglycon 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)- Ccris 7633 8-glycoloyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-Naphthacenedione Doxorubicin aglycone Doxorubicinone Epirubicin aglycone 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)- 7,8,9,10-Tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxy acetyl)-1-methoxy-(8S-cis)-5,12-naphthacenedione ADRIAMYCINONE (8S,10S)-7,8,9,10-Tetrahydro-6,8,10,11-tetrahydroxy 8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione adriamycinaglycone Doxorubicinone (Doxorubicin EP Impurity D,Epirubicin EP Impurity A) 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)- Doxorubicin Hydrochloride EP Impurity D Doxorubicinone-13C-D3 DoxorubicinoneQ: What is Doxorubicinone Q: What is the CAS Number of Doxorubicinone Q: What is the storage condition of Doxorubicinone Q: What are the applications of Doxorubicinone Doxorubicinone ((8S,10S)-6,8,10,11-Tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetr (1225758) (8S,10S)-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione (doxorubicin aglycone, doxorubicinone). (8S,10S)-10[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-(bromoacetyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione, Doxorubicin EP Impurity D/Epirubicin hydrochloride EP impurity A D2-N-Nitroso desmethyldoxycycline 24385-10-2 C21H18O9 Intermediates & Fine Chemicals Pharmaceuticals Metabolites & Impurities Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals