U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of DETORUBICIN HYDROCHLORIDE

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

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

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

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
A prospective study of detorubicin in malignant mesothelioma.
1985 Nov 1
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 05:00:13 GMT 2023
Edited
by admin
on Sat Dec 16 05:00:13 GMT 2023
Record UNII
XMI0YV2GFR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DETORUBICIN HYDROCHLORIDE
Common Name English
ACETIC ACID, DIETHOXY-, 2-(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, HYDROCHLORIDE, (2S-CIS)-
Systematic Name English
NSC-292652
Code English
Code System Code Type Description
FDA UNII
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
PRIMARY
NSC
292652
Created by admin on Sat Dec 16 05:00:13 GMT 2023 , Edited by admin on Sat Dec 16 05:00:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID70982844
Created by admin on Sat Dec 16 05:00:13 GMT 2023 , Edited by admin on Sat Dec 16 05:00:13 GMT 2023
PRIMARY
PUBCHEM
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
PRIMARY
CAS
64291-45-8
Created by admin on Sat Dec 16 05:00:13 GMT 2023 , Edited by admin on Sat Dec 16 05:00:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
264-770-1
Created by admin on Sat Dec 16 05:00:13 GMT 2023 , Edited by admin on Sat Dec 16 05:00:13 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY