Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H39NO14.ClH |
Molecular Weight | 710.122 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(C=CC=C4OC)C3=O)C(O)=C12)C(=O)COC(=O)C(OCC)OCC)O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5
InChI
InChIKey=PJODMULXZJQLDJ-NMELVCTCSA-N
InChI=1S/C33H39NO14.ClH/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;1H/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 |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
|
Cardiotoxicity and comparative pharmacokinetics of six anthracyclines in the rabbit. | 1980 Oct |
|
Detorubicin--an active anthracycline in untreated metastatic melanoma. | 1985 Nov |
|
A prospective study of detorubicin in malignant mesothelioma. | 1985 Nov 1 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 05:00:13 GMT 2023
by
admin
on
Sat Dec 16 05:00:13 GMT 2023
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Record UNII |
XMI0YV2GFR
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Record Status |
Validated (UNII)
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Record Version |
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-
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XMI0YV2GFR
Created by
admin on Sat Dec 16 05:00:13 GMT 2023 , Edited by admin on Sat Dec 16 05:00:13 GMT 2023
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292652
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DTXSID70982844
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21119277
Created by
admin on Sat Dec 16 05:00:13 GMT 2023 , Edited by admin on Sat Dec 16 05:00:13 GMT 2023
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64291-45-8
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admin on Sat Dec 16 05:00:13 GMT 2023 , Edited by admin on Sat Dec 16 05:00:13 GMT 2023
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264-770-1
Created by
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |