Stereochemistry | ABSOLUTE |
Molecular Formula | C33H39NO14 |
Molecular Weight | 673.6611 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(OCC)C(=O)OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C3=C(O)C4=C(C(=O)C5=C(C4=O)C(OC)=CC=C5)C(O)=C3C1
InChI
InChIKey=XZSRRNFBEIOBDA-CFNBKWCHSA-N
InChI=1S/C33H39NO14/c1-5-44-32(45-6-2)31(41)46-13-20(35)33(42)11-16-23(19(12-33)48-21-10-17(34)26(36)14(3)47-21)30(40)25-24(28(16)38)27(37)15-8-7-9-18(43-4)22(15)29(25)39/h7-9,14,17,19,21,26,32,36,38,40,42H,5-6,10-13,34H2,1-4H3/t14-,17-,19-,21-,26+,33-/m0/s1
Molecular Formula | C33H39NO14 |
Molecular Weight | 673.6611 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Detorubicin is a semi-synthetic derivative of the anthracycline antineoplastic antibiotic. It intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent also produces toxic free-radical intermediates and interacts with cell membrane lipids causing lipid peroxidation. Detorubicin is less toxic than daunorubicin. Although it showed some clinical activity, the drug appeared to have no particular advantage over doxorubicin except for demonstrated activity against malignant melanoma. Unfortunately, detorubicin clearly has cardiac toxicity – in clinical trial, one patient developed congestive heart failure and other patients revealed endomyocardial biopsy evidence of cardiac toxicity.