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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H35N3O10
Molecular Weight 645.6558
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ZORUBICIN

SMILES

[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(C=CC=C4OC)C3=O)C(O)=C12)C(C)=NNC(=O)C5=CC=CC=C5)O[C@H]6C[C@H](N)[C@H](O)[C@H](C)O6

InChI

InChIKey=FBTUMDXHSRTGRV-BJISBDEGSA-N
InChI=1S/C34H35N3O10/c1-15-28(38)20(35)12-23(46-15)47-22-14-34(44,16(2)36-37-33(43)17-8-5-4-6-9-17)13-19-25(22)32(42)27-26(30(19)40)29(39)18-10-7-11-21(45-3)24(18)31(27)41/h4-11,15,20,22-23,28,38,40,42,44H,12-14,35H2,1-3H3,(H,37,43)/t15-,20-,22-,23-,28+,34-/m0/s1

HIDE SMILES / InChI

Description

Zorubicin is a benzoylhydrazone derivative of the anthracycline antineoplastic antibiotic daunorubicin, but it introduces lower cardiomyopathy and bone marrow toxicity. Zorubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair as well as RNA and protein synthesis. The cytotoxic effect results from intercalation between DNA pairs. To minimize toxicity, individualized dose regimens are given preferentially over prolonged periods of time by carefully inspecting i.v. administration to prevent extravasation.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
6.46 µM [IC50]