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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 of LADIRUBICIN

SMILES

[H][C@@]1(C[C@@H]([C@H](OS(C)(=O)=O)[C@H](C)O1)N2CC2)O[C@H]3C[C@@](O)(CC4=C3C(O)=C5C(=O)C6=C(C=CC=C6)C(=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

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

Curator's Comment: Known to be CNS penetrant in mice. Human data not available.

Approval Year

PubMed

PubMed

TitleDatePubMed
Sequence-specific DNA interactions by novel alkylating anthracycline derivatives.
1995 Dec
Pharmacological and toxicological aspects of 4-demethoxy-3'-deamino-3'-aziridinyl-4'-methylsulphonyl-daunorubicin (PNU-159548): a novel antineoplastic agent.
2001 Mar 1
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 Mar 1
4-Demethoxy-3'-deamino-3'-aziridinyl-4'-methylsulphonyl-daunorubicin (PNU-159548): a promising new candidate for chemotherapeutic treatment of osteosarcoma patients.
2005 Sep
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:49:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:14 GMT 2023
Record UNII
U395ERO49H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LADIRUBICIN
INN   WHO-DD  
INN  
Official Name English
(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
Common Name English
Ladirubicin [WHO-DD]
Common Name English
ladirubicin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
Code System Code Type Description
PUBCHEM
216232
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
FDA UNII
U395ERO49H
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID301031257
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
CAS
171047-47-5
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103926
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
NCI_THESAURUS
C83861
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
SMS_ID
300000036977
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
INN
7958
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
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