SJG-136

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C31H32N4O6
Molecular Weight	556.609
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC(=C)CN1C(=O)C3=C(C=C(OCCCOC4=CC5=C(C=C4OC)C(=O)N6CC(=C)C[C@@]6([H])C=N5)C(OC)=C3)N=C2

InChI

InChIKey=RWZVMMQNDHPRQD-SFTDATJTSA-N

InChI=1S/C31H32N4O6/c1-18-8-20-14-32-24-12-28(26(38-3)10-22(24)30(36)34(20)16-18)40-6-5-7-41-29-13-25-23(11-27(29)39-4)31(37)35-17-19(2)9-21(35)15-33-25/h10-15,20-21H,1-2,5-9,16-17H2,3-4H3/t20-,21-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02034227 | https://clinicaltrials.gov/ct2/show/NCT01200797 | https://www.ncbi.nlm.nih.gov/pubmed/21188379

BN-2629 (also known as SJG-136 and SG2000), a dimeric pyrrolobenzodiazepine that binds in the minor groove of DNA and produces G-G interstrand cross-links via reactive N(10)-C(11)/N(10')-C(ll') imine/carbinolamine moieties. This drug was investigated in phase II clinical trials in patients with epithelial ovarian, primary peritoneal, or fallopian tube cancer, however, these studied were terminated because of the slow accrual. In addition, BN-2629 participated in phase I/II trial in participants with advanced chronic lymphocytic leukemia and acute myeloid leukemia, but Spirogen also terminated these studies.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11262084	Crosslinking Agent 81

PubMed

Title	Date	PubMed
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.	2001 Mar 1	11262084
LC-MS/MS assay and dog pharmacokinetics of the dimeric pyrrolobenzodiazepine SJG-136 (NSC 694501).	2006 Aug 7	16730244
Pharmacokinetics, pharmacodynamics and metabolism of the dimeric pyrrolobenzodiazepine SJG-136 in rats.	2011 Sep	21188379

Sample Use Guides

In Vivo Use Guide

Acute Myeloid Leukemia; Chronic Lymphocytic Leukemia: 15 µg/m2/day intravenous doses of SG2000 until Maximum Tolerated Dose is determined.intravenous doses given on Days 1, 2, and 3 of each 21-day cycle (1 to 6 cycles).

Route of Administration: Intravenous

Name

Type

Language

SJG-136

Common Name

English

BN-2629

Code

English

SP-2001

Code

English

SJG 136 [WHO-DD]

Common Name

English

NSC-694501

Code

English

SG-2000

Code

English

UP-2001

Code

English

5H-PYRROLO(2,1-C)(1,4)BENZODIAZEPIN-5-ONE, 8,8'-(1,3-PROPANEDIYLBIS(OXY))BIS(1,2,3,11A-TETRAHYDRO-7-METHOXY-2-METHYLENE-, (11AS,11'AS)-

Systematic Name

English

(6AS)-3-(3-(((6AS)-2-METHOXY-8-METHYLENE-11-OXO-7,9-DIHYDRO-6AH-PYRROLO(2,1-C)(1,4)BENZODIAZEPIN-3-YL)OXY)PROPOXY)-2-METHOXY-8-METHYLENE-7,9-DIHYDRO-6AH-PYRROLO(2,1-C)(1,4)BENZODIAZEPIN-11-ONE

Systematic Name

English

Code System Code Type Description

DRUG BANK

DB11965