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Details

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
Structure of DETORUBICIN

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

HIDE SMILES / InChI

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

Description

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.

Approval Year

PubMed

Patents

Substance Class Chemical
Record UNII
822EC3XEJZ
Record Status Validated (UNII)
Record Version