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54083-22-6

54083-22-6 Structure

54083-22-6 Structure
IdentificationBack Directory
[Name]

Zorubicin
[CAS]

54083-22-6
[Synonyms]

ZORUBICIN
RUBIDAZON
Rubidazone
Ccris 2260
Brn 1417621
Zorubicin [inn]
Daunomycin benzoylhydrazone
Benzoylhydrazone daunorubicin
N-[1-[(2S,4S)-4-(4-Amino-5-hydroxy-6-methyloxan-2-yl)oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethylideneamino]benzamide
N-[(E)-1-[(2S,4S)-4-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethylideneamino]benzamide
Benzoic acid, 1-(2S,4S)-4-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenylethylidenehydrazide
Benzoic acid 2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxonaphthacen-2-yl]ethylidene] hydrazide
Benzoic acid, 2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]ethylidene]hydrazide
Benzoic acid, (1-(4-((3-amino-2,3,6-trideoxy-alpha,L-lyxo-hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl)ethylidene)hydrazide, (2S-cis)-
[Molecular Formula]

C34H35N3O10
[MDL Number]

MFCD00866363
[MOL File]

54083-22-6.mol
[Molecular Weight]

645.66
Chemical PropertiesBack Directory
[Boiling point ]

675.08°C (rough estimate)
[density ]

1.2920 (rough estimate)
[refractive index ]

1.7800 (estimate)
Hazard InformationBack Directory
[Originator]

Zorubicin Hydrochloride,ZYF Pharm Chemical
[Uses]

Antineoplastic.
[Manufacturing Process]

9.024 g daunorubicin-hydrochloride (its preparation and physicochemical properties have been described in British Patent Specification No 985 598) was dissolved in 800 ml ethanol and mixed with 2.5 ml acetic acid and 2.162 g benzoyl hydrazide and heated for 24 hours at 60°C. On cooling the obtained precipitate was filtered off, washed with 100 ml of ethanol and dried in vacuum at 20°C. It was dissolved in water and small quantity of insoluble product was filtered off, the filtrate was lyophilized. (1-(4-((3-Amino-2,3,6- trideoxy-α,L-lyxohexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12- trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl)ethylidene)hydrazide dihydrochloride (zorubicin) was obtained as red-orange crystalline powder; [α] D 20 = -50° (c=0.2 in water). The compound may be employed in the form of different non-toxic salts such as benzoates, fumarates, maleates, tartrates and so on. The best among these compounds proves to be daunorubicin benzoylhydrazone (rubidazone), which is less cardiotoxic (French Pat. No. 1,578,722 published in 1967, Class CO7d).
[Therapeutic Function]

Antineoplastic, Antileukemic
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