Doxorubicinone Chemical 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 Information

HS Code 

29147000

Doxorubicinone Usage And Synthesis

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).

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.

Doxorubicinone(24385-10-2)Related Product Information

• Galarubicin hydrochloride
• Leurubicin
• Adriamycin
• Doxorubicinone
• Pirarubicin
• Nemorubicin
• Epirubicin
• EPIRUBICIN HYDROCHLORIDE
• 7-O-(2,6-Dideoxy-2-fluorotalopyranose)adriamycinone
• NAPHTHACENE
• N-trifluoroacetyladriamycin
• Esorubicin
• Detorubicin
• 7-O-(2,6-dideoxy-2-fluoro--5-C-(trifluoromethyl)talopyranosyl)adriamycinone
• N-(3-pyridylmethyl)adriamycin
• N,N-dimethyldoxorubicin
• N-trifluoroacetyladriamycin-14-O-hemiadipate
• 14-salicyloyldaunorubicin