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

COC1=CC2=C(C=C1OCCCOC3=C(OC)C=C4C(=C3)N=C[C@@H]5CC(=C)CN5C4=O)N=C[C@@H]6CC(=C)CN6C2=O

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

Molecular Formula	C31H32N4O6
Molecular Weight	556.609
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11262084	Crosslinking Agent 83

PubMed

Title	Date	PubMed
Pharmacokinetics, pharmacodynamics and metabolism of the dimeric pyrrolobenzodiazepine SJG-136 in rats.	2011-09	21188379
LC-MS/MS assay and dog pharmacokinetics of the dimeric pyrrolobenzodiazepine SJG-136 (NSC 694501).	2006-08-07	16730244
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.	2001-03-01	11262084

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:22 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:22 GMT 2025`
Record UNII	KT0ZQ64X1A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BN-2629

Preferred Name

English

SJG-136

Common Name

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