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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

[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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
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
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:06:15 GMT 2023
Edited
by admin
on Fri Dec 15 16:06:15 GMT 2023
Record UNII
822EC3XEJZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DETORUBICIN
INN  
INN  
Official Name English
ACETIC ACID, 2,2-DIETHOXY-, 2-((2S,4S)-4-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-1,2,3,4,6,11-HEXAHYDRO-2,5,12-TRIHYDROXY-7-METHOXY-6,11-DIOXO-2-NAPHTHACENYL)-2-OXOETHYL ESTER
Common Name English
detorubicin [INN]
Common Name English
GLYOXYLIC ACID 32-ESTER WITH DOXORUBICIN, 2-(DIETHYL ACETAL)
Common Name English
Classification Tree Code System Code
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
Code System Code Type Description
EPA CompTox
DTXSID601024380
Created by admin on Fri Dec 15 16:06:15 GMT 2023 , Edited by admin on Fri Dec 15 16:06:15 GMT 2023
PRIMARY
EVMPD
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
PRIMARY
NCI_THESAURUS
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
PRIMARY
FDA UNII
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
PRIMARY
ChEMBL
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
PRIMARY
CAS
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
PRIMARY
MESH
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
PRIMARY
SMS_ID
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
PRIMARY
PUBCHEM
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
PRIMARY
INN
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
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY