BISNAFIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H28N6O8
Molecular Weight	624.6001
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](CNCCNC[C@@H](C)N1C(=O)C2=CC=CC3=CC(=CC(C1=O)=C23)[N+]([O-])=O)N4C(=O)C5=CC=CC6=CC(=CC(C4=O)=C56)[N+]([O-])=O

InChI

InChIKey=PXBZKHOQHTVCSQ-QZTJIDSGSA-N

InChI=1S/C32H28N6O8/c1-17(35-29(39)23-7-3-5-19-11-21(37(43)44)13-25(27(19)23)31(35)41)15-33-9-10-34-16-18(2)36-30(40)24-8-4-6-20-12-22(38(45)46)14-26(28(20)24)32(36)42/h3-8,11-14,17-18,33-34H,9-10,15-16H2,1-2H3/t17-,18-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9740543 | https://www.ncbi.nlm.nih.gov/pubmed/8174127

Bisnafide (previously known as DMP 840), a bis-naphthalimide derivative that was developed by Bristol-Myers Squibb as a potential anticancer agent. Bisnafide acts as DNA intercalator and topo II inhibitor. This drug participated in phase I clinical trials in pediatric patients with refractory solid tumors. However, further, development has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Efficacy of DMP 840: a novel bis-naphthalimide cytotoxic agent with human solid tumor xenograft selectivity.	1994 Jan 1	8261436
Phase I study of DMP 840 in pediatric patients with refractory solid tumors.	1998	9740543
Determination of bisnafide, a novel bis-naphthalimide anticancer agent, in human plasma by high-performance liquid chromatography with UV detection.	1998 Jul	9656154
Validation of cleaning procedures for highly potent drugs. II. Bisnafide.	1998 Nov	9834949

Sample Use Guides

In Vivo Use Guide

10 patients with refractory pediatric solid tumors to this Phase I study of DMP 840 given intravenously by short infusion daily for 5 days

Route of Administration: Intravenous

In Vitro Use Guide

DMP 840 exhibits potent antiproliferative activity in vitro against a variety of human and murine leukemia and solid tumor cell lines in culture, with inhibitory doses that reduce the number of treated cells to one half (IC50) values ranging from 2.3 to 53 nM.

Name

Type

Language

BISNAFIDE

Official Name

English

Bisnafide [WHO-DD]

Common Name

English

bisnafide [INN]

Common Name

English

1H-BENZ(DE)ISOQUINOLINE-1,3(2H)-DIONE, 2,2'-(1,2-ETHANEDIYLBIS(IMINO((1R)-1-METHYL-2,1-ETHANEDIYL)))BIS(5-NITRO-

Common Name

English

N,N'-(ETHYLENEBIS(IMINO((R)-1-METHYLETHYLENE)))BIS(3-NITRONAPHTHALIMIDE)

Common Name

English

1H-BENZ(DE)ISOQUINOLINE-1,3(2H)-DIONE, 2,2'-(1,2-ETHANEDIYLBIS(IMINO(1-METHYL-2,1-ETHANEDIYL)))BIS(5-NITRO-, (R-(R*,R*))-

Common Name

English

VERSALUMA

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C582