LADIRUBICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H31NO11S
Molecular Weight	601.622
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1O[C@H](C[C@@H]([C@@H]1OS(C)(=O)=O)N2CC2)O[C@H]3C[C@@](O)(CC4=C3C(O)=C5C(=O)C6=CC=CC=C6C(=O)C5=C4O)C(C)=O

InChI

InChIKey=VMDWTZZCNDEKIO-CBNJBKGYSA-N

InChI=1S/C29H31NO11S/c1-13-28(41-42(3,37)38)18(30-8-9-30)10-20(39-13)40-19-12-29(36,14(2)31)11-17-21(19)27(35)23-22(26(17)34)24(32)15-6-4-5-7-16(15)25(23)33/h4-7,13,18-20,28,34-36H,8-12H2,1-3H3/t13-,18-,19-,20-,28+,29-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H31NO11S
Molecular Weight	601.622
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8595123 | https://www.ncbi.nlm.nih.gov/pubmed/11280756

LADIRUBICIN is an idarubicin derivative with potential antineoplastic activity. Its primary effect is a DNA alkylation with sequence specificity similar to that of conventional nitrogen mustards. It possesses a wide spectrum antitumor activity against rapidly proliferating murine leukemias and on slowly growing transplantable human tumor xenografts.

CNS Activity

Approval Year

PubMed

Title	Date	PubMed
4-Demethoxy-3'-deamino-3'-aziridinyl-4'-methylsulphonyl-daunorubicin (PNU-159548): a promising new candidate for chemotherapeutic treatment of osteosarcoma patients.	2005-09	16140527
Pharmacological and toxicological aspects of 4-demethoxy-3'-deamino-3'-aziridinyl-4'-methylsulphonyl-daunorubicin (PNU-159548): a novel antineoplastic agent.	2001-03-01	11280756
4-Demethoxy-3'-deamino-3'-aziridinyl-4'-methylsulphonyl-daunorubicin (PNU-159548), a novel anticancer agent active against tumor cell lines with different resistance mechanisms.	2001-03-01	11280757
Sequence-specific DNA interactions by novel alkylating anthracycline derivatives.	1995-12	8595123

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:09:50 GMT 2025` Edited by `admin` on `Mon Mar 31 18:09:50 GMT 2025`
Record UNII	U395ERO49H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(1S,3S-3-ACETYL-1,2,3,4,6,11,HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-(1-AZIRIDINYL)-2,3,6-TRIDEOXY-4-O-(METHYLSULFONYL)-.ALPHA.-L-LYXO-HEXOPYRANOSIDE

Preferred Name

English

LADIRUBICIN

Official Name

English

Ladirubicin [WHO-DD]

Common Name

English

ladirubicin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1594