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
SMILES
[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)C(=O)COC(=O)C(OCC)OCC
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 |
|
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.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Low heart and skin toxicity of a tetrahydropyranyl derivative of adriamycin (THP-ADM) as observed by electron and light microscopy. | 1979 Oct |
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Cardiotoxicity and comparative pharmacokinetics of six anthracyclines in the rabbit. | 1980 Oct |
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Detorubicin--an active anthracycline in untreated metastatic melanoma. | 1985 Nov |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:06:15 GMT 2023
by
admin
on
Fri Dec 15 16:06:15 GMT 2023
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Record UNII |
822EC3XEJZ
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Record Status |
Validated (UNII)
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Record Version |
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-
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1594
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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Code System | Code | Type | Description | ||
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DTXSID601024380
Created by
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SUB07013MIG
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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C1066
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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822EC3XEJZ
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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CHEMBL2104401
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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66211-92-5
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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C017218
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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100000083216
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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6917660
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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PRIMARY | |||
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4611
Created by
admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |