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36508-71-1

36508-71-1 Structure

36508-71-1 Structure
IdentificationBack Directory
[Name]

ZORUBICIN HCL
[CAS]

36508-71-1
[Synonyms]

rubidaz
22050r.p.
nsc-164011
ZORUBICIN HCL
rp22,050hydrochloride
rubidazone,monohydrochloride
daunorubicin,benzoylhydrazone,monohydrochloride
benzoicacidhydrazide,3-hydrazonewithdaunorubicin,monohydrochloride
(2S-cis)-Benzoic acid[1-[4-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hex-opyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-napthacenyl]ethylidene]hydrazide hydroehloride
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, monohydrochloride
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, monohydrochloride, (2S-cis)-
[EINECS(EC#)]

253-076-4
[Molecular Formula]

C34H36ClN3O10
[MDL Number]

MFCD00941450
[MOL File]

36508-71-1.mol
[Molecular Weight]

682.12
Chemical PropertiesBack Directory
[alpha ]

D20 -50° (c = 0.2 in water)
[solubility ]

DMSO (Slightly), Methanol (Slightly), Water (Slightly)
[form ]

Solid
[color ]

Orange to Dark Red
[Stability:]

Light Sensitive
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Benzoyl hydrazine-->Daunorubicin hydrochloride-->Aminoguanidine
Hazard InformationBack Directory
[Chemical Properties]

Obtained as an orange-red crystalline powder from ethanol. [α]D 20-50° (C = 0.2, water). UV absorption maxima (methanol): 232.5, 253, 480, 495 nm (ε 40225, 35300, 10480, 10300). Acute toxicity LD50 in mice (mg/kg): 13.66 subcutaneously, 4.42 intraperitoneally, and 8.50 intravenously.
[Originator]

Zorubicin Hydrochloride,ZYF Pharm Chemical
[Uses]

Antineoplastic.
[Uses]

Zorubicin Hydrochloride is an anthracycline anti-cancer drug related to Daunorubicin (D194500).
[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
Safety DataBack Directory
[Toxicity]

LD50 in mice (mg/kg): 13.66 s.c., 4.42 i.p., 8.50 i.v. (Maral, 1972)
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