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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H32FNO13
Molecular Weight 633.5724
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALARUBICIN

SMILES

[H][C@@]5(O[C@H]1C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(OC)C=CC=C4C3=O)C(O)=C12)C(=O)COC(=O)CCN)O[C@@H](C)[C@@H](O)[C@@H](O)[C@H]5F

InChI

InChIKey=CKXIPXAIFMTQCS-LRDUUELOSA-N
InChI=1S/C30H32FNO13/c1-11-23(35)28(40)22(31)29(44-11)45-15-9-30(41,16(33)10-43-17(34)6-7-32)8-13-19(15)27(39)21-20(25(13)37)24(36)12-4-3-5-14(42-2)18(12)26(21)38/h3-5,11,15,22-23,28-29,35,37,39-41H,6-10,32H2,1-2H3/t11-,15-,22+,23+,28-,29-,30-/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H32FNO13
Molecular Weight 633.5724
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

GALARUBICIN (DA-125) is an anthracycline derivative with anticancer activity, containing fluorine. The mechanism of action of this drug lies in inhibition of nucleic acid synthesis through intercalation with DNA. Because the structure and DNA-intercalating properties of DA-125 are similar to adriamycin, the cytotoxic effects of the two anthracyclines probably have similar biochemical mechanisms. Preclinical studies suggest that it may have greater activity and less cardiac toxicity than adriamycin. In a rodent study, administration of D-125 in higher dose levels (25 to 50 mg/kg) has been shown to result in testicular damage.

Approval Year

PubMed

PubMed

TitleDatePubMed
DA-125, a novel anthracycline derivative showing high-affinity DNA binding and topoisomerase II inhibitory activities, exerts cytotoxicity via c-Jun N-terminal kinase pathway.
2001 Jun
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:02:34 GMT 2023
Edited
by admin
on Fri Dec 15 16:02:34 GMT 2023
Record UNII
6F39648E92
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GALARUBICIN
INN   WHO-DD  
INN  
Official Name English
Galarubicin [WHO-DD]
Common Name English
galarubicin [INN]
Common Name English
(8S,10S)-10-((2.6-DIDEOXY-2-FLUORO-.ALPHA.-L-TALOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE 8(SUP 2)-ESTER WITH .BETA.-ALANINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C81422
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
FDA UNII
6F39648E92
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
SMS_ID
100000087256
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106451
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
INN
7826
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
EVMPD
SUB02302MIG
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
CAS
195612-80-7
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
PUBCHEM
114759
Created by admin on Fri Dec 15 16:02:34 GMT 2023 , Edited by admin on Fri Dec 15 16:02:34 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY