BIZELESIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H36Cl2N8O5
Molecular Weight	815.703
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CNC2=C(O)C=C3N(C[C@@H](CCl)C3=C12)C(=O)C4=CC5=C(N4)C=CC(NC(=O)NC6=CC7=C(NC(=C7)C(=O)N8C[C@@H](CCl)C9=C%10C(C)=CNC%10=C(O)C=C89)C=C6)=C5

InChI

InChIKey=FONKWHRXTPJODV-DNQXCXABSA-N

InChI=1S/C43H36Cl2N8O5/c1-19-15-46-39-33(54)11-31-37(35(19)39)23(13-44)17-52(31)41(56)29-9-21-7-25(3-5-27(21)50-29)48-43(58)49-26-4-6-28-22(8-26)10-30(51-28)42(57)53-18-24(14-45)38-32(53)12-34(55)40-36(38)20(2)16-47-40/h3-12,15-16,23-24,46-47,50-51,54-55H,13-14,17-18H2,1-2H3,(H2,48,49,58)/t23-,24-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12702533 | https://www.ncbi.nlm.nih.gov/pubmed/9816280 | https://www.ncbi.nlm.nih.gov/pubmed/11895900

Bizelesin (previously known as U-77779 or NSC 615291), a cyclopropylpyrroloindole antitumor agent acts as a bifunctional alkylating agent and produces DNA interstrand cross-links. This drug participated in phase I clinical trials in patients with advanced solid malignancies, however further development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
DNA interstrand cross-linking, DNA sequence specificity, and induced conformational changes produced by a dimeric analog of (+)-CC-1065.	1991 Nov	1662513
Preclinical antitumor activity of bizelesin in mice.	1996 Jul	9816280
A Phase I study of bizelesin (NSC 615291) in patients with advanced solid tumors.	2002 Mar	11895900
SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity: part 2: efficacy evaluations.	2004 Sep 15	15374987

Sample Use Guides

In Vivo Use Guide

Patients with advanced solid malignancies were treated with escalating doses of bizelesin as an i.v. bolus injection every 4 weeks. The selection of the specific starting dose, 0.1 micro g/m(2), which was equivalent to one-tenth the toxic dose low in dogs, factored in large interspecies differences in myelotoxicity as gauged using an ex vivo hematopoietic colony-forming assay

Route of Administration: Intravenous

Name

Type

Language

BIZELESIN

Official Name

English

NSC-615291

Code

English

bizelesin [INN]

Common Name

English

U 77779

Code

English

BENZO(1,2-B:4,3-B')DIPYRROL-4-OL, 6,6'-(CARBONYLBIS(IMINO-1H-INDOLE-5,2-DIYLCARBONYL))BIS(8-(CHLOROMETHYL)-3,6,7,8-TETRAHYDRO-1-METHYL-, (S-(R*,R*))-

Common Name

English

U-77779

Code

English

1,3-BIS(2-(((S)-1-(CHLOROMETHYL)-1,6-DIHYDRO-5-HYDROXY-8-METHYLBENZO(1,2-B:4,3-B')DIPYRROL-3(2H)-YL)CARBONYL)INDOL-5-YL)UREA

Common Name

English

BIZELESIN [USAN]

Common Name

English

Bizelesin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2156