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Details

Stereochemistry ACHIRAL
Molecular Formula C20H22N4O2
Molecular Weight 350.415
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of C-1311

SMILES

CCN(CC)CCNc1ccc2c3c1c(=O)c4cc(ccc4n3cn2)O

InChI

InChIKey=CUNDRHORZHFPLY-UHFFFAOYSA-N
InChI=1S/C20H22N4O2/c1-3-23(4-2)10-9-21-15-6-7-16-19-18(15)20(26)14-11-13(25)5-8-17(14)24(19)12-22-16/h5-8,11-12,21,25H,3-4,9-10H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C20H22N4O2
Molecular Weight 350.415
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

C-1311 is an imidazoacridinone analog. It is a next-generation investigational anticancer drug. It is an antitumor inhibitor of topoisomerase II and FMS-like tyrosine kinase 3 receptor. It was evaluated in phase I and II clinical trials for the treatment of various types of tumors. Mild treatment-related adverse events were thrombocytopenia, anemia, nausea, vomiting and diarrhea. Serious adverse event is neutropenia.

Approval Year

PubMed

PubMed

TitleDatePubMed
5-[(Aminoalkyl)amino]imidazo[4,5,1-de]acridin-6-ones as a novel class of antineoplastic agents. Synthesis and biological activity.
1990 Jan
Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias.
1992 Jan 24
Cell killing by the novel imidazoacridinone antineoplastic agent, C-1311, is inhibited at high concentrations coincident with dose-differentiated cell cycle perturbation.
1996 Nov
Development and validation of an LC-UV method for the quantification and purity determination of the novel anticancer agent C1311 and its pharmaceutical dosage form.
2005 Sep 1
Pharmaceutical development of a parenteral lyophilised dosage form for the novel anticancer agent C1311.
2005 Sep-Oct
Patents

Sample Use Guides

In Vivo Use Guide
Sources: DOI: 10.1200/jco.2008.26.15_suppl.1055
The initial dose was 480 mg/m2, 1 hr IV infusion on d 1, 8, and 15 of a 28 day cycle.
Route of Administration: Intravenous
In Vitro Use Guide
Acute treatments (3 h) of the a human tumour line (HeLa S3) revealed that cells exposed to C-1311 levels, which first induced persistent G2 arrest (0.5 ug/ml), subsequently died from this compartment, while doses exceeding these levels (1.0 ug/ml), paradoxically, did not cause the same extensive cell death.
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:42:56 UTC 2021
Edited
by admin
on Sat Jun 26 14:42:56 UTC 2021
Record UNII
MZ4Y5H4OAB
Record Status Validated (UNII)
Record Version
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Name Type Language
C-1311
Common Name English
NSC-645809
Code English
XLS-002
Common Name English
SYMADEX
Common Name English
C 1311
Common Name English
IMIDAZOACRIDONE
Systematic Name English
Code System Code Type Description
EPA CompTox
138154-39-9
Created by admin on Sat Jun 26 14:42:56 UTC 2021 , Edited by admin on Sat Jun 26 14:42:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL338604
Created by admin on Sat Jun 26 14:42:56 UTC 2021 , Edited by admin on Sat Jun 26 14:42:56 UTC 2021
PRIMARY
MESH
C098965
Created by admin on Sat Jun 26 14:42:56 UTC 2021 , Edited by admin on Sat Jun 26 14:42:56 UTC 2021
PRIMARY
FDA UNII
MZ4Y5H4OAB
Created by admin on Sat Jun 26 14:42:56 UTC 2021 , Edited by admin on Sat Jun 26 14:42:56 UTC 2021
PRIMARY
PUBCHEM
132127
Created by admin on Sat Jun 26 14:42:56 UTC 2021 , Edited by admin on Sat Jun 26 14:42:56 UTC 2021
PRIMARY
CAS
138154-39-9
Created by admin on Sat Jun 26 14:42:56 UTC 2021 , Edited by admin on Sat Jun 26 14:42:56 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
time- and concentration-dependent inhibitor
Related Record Type Details
ACTIVE MOIETY