GALARUBICIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H32FNO13.ClH
Molecular Weight	670.033
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[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=PISPJMVXLMWWNB-ZZBYHBTRSA-N

InChI=1S/C30H32FNO13.ClH/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;1H/t11-,15-,22+,23+,28-,29-,30-;/m0./s1

HIDE SMILES / InChI

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

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 Jun	11459204

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:32:38 GMT 2023` Edited by `admin` on `Sat Dec 16 08:32:38 GMT 2023`
Record UNII	C7EKF2I37Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALARUBICIN HYDROCHLORIDE

Common Name

English

DA-125

Code

English

.BETA.-ALANINE, 2-((2S,4S)-4-((2,6-DIDEOXY-2-FLUORO-.ALPHA.-L-TALOPYRANOSYL)OXY)-1,2,3,4,6,11-HEXAHYDRO-2,5,12-TRIHYDROXY-7-METHOXY-6,11-DIOXO-2-NAPHTHACENYL)-2-OXOETHYL ESTER, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

140637-86-1