GALARUBICIN

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 Search

SMILES

COC1=CC=CC2=C1C(=O)C3=C(C2=O)C(O)=C4C[C@](O)(C[C@H](O[C@@H]5O[C@@H](C)[C@@H](O)[C@@H](O)[C@H]5F)C4=C3O)C(=O)COC(=O)CCN

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14969343 | https://www.ncbi.nlm.nih.gov/pubmed/11459204 | https://www.ncbi.nlm.nih.gov/pubmed/10560588

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

Title	Date	PubMed
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.	2001-06	11459204

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:17:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:17:12 GMT 2025`
Record UNII	6F39648E92
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALARUBICIN

Official 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

Preferred Name

English

Galarubicin [WHO-DD]

Common Name

English

galarubicin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1594