U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H24N4O2
Molecular Weight 388.4623
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XR-11576

SMILES

COC1=C2C=CC3=C(N=C4C(C=CC=C4C(=O)N[C@H](C)CN(C)C)=N3)C2=CC=C1

InChI

InChIKey=ACAXGYADTLFREX-CQSZACIVSA-N
InChI=1S/C23H24N4O2/c1-14(13-27(2)3)24-23(28)17-8-5-9-18-22(17)26-21-16-7-6-10-20(29-4)15(16)11-12-19(21)25-18/h5-12,14H,13H2,1-4H3,(H,24,28)/t14-/m1/s1

HIDE SMILES / InChI

Molecular Formula C23H24N4O2
Molecular Weight 388.4623
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Substance Class Chemical
Created
by admin
on Tue Apr 01 16:33:56 GMT 2025
Edited
by admin
on Tue Apr 01 16:33:56 GMT 2025
Record UNII
Q2L4XU3YX6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
XR-11576
Code English
XR11576
Preferred Name English
BENZO(A)PHENAZINE-11-CARBOXAMIDE, N-((1R)-2-(DIMETHYLAMINO)-1-METHYLETHYL)-4-METHOXY-
Systematic Name English
N-((1R)-2-(DIMETHYLAMINO)-1-METHYL-ETHYL)-4-METHOXY-BENZO(A)PHENAZINE-11-CARBOXAMIDE
Systematic Name English
MLN-576
Code English
Code System Code Type Description
PUBCHEM
9886593
Created by admin on Tue Apr 01 16:33:56 GMT 2025 , Edited by admin on Tue Apr 01 16:33:56 GMT 2025
PRIMARY
CAS
346689-77-8
Created by admin on Tue Apr 01 16:33:56 GMT 2025 , Edited by admin on Tue Apr 01 16:33:56 GMT 2025
PRIMARY
FDA UNII
Q2L4XU3YX6
Created by admin on Tue Apr 01 16:33:56 GMT 2025 , Edited by admin on Tue Apr 01 16:33:56 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY
Mechanism of Action: DNA topoisomerase I inhibitors, Type II DNA topoisomerase inhibitors; Highest Development Phase: Discontinued for Cancer
ACTIVE MOIETY
XR11576, a novel phenazine, was developed as an inhibitor of both topoisomerase I and II. XR11576 demonstrated potent cytotoxic activity against a variety of human and murine tumor cell lines (IC50=6-47 nM). Its activity profile was comparable to or better than that of many widely used anticancer drugs.