C-1311

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H22N4O2
Molecular Weight	350.4143
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCNC1=CC=C2N=CN3C2=C1C(=O)C4=C3C=CC(O)=C4

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	350.4143
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20031390 | http://adisinsight.springer.com/drugs/800007613 | http://clincancerres.aacrjournals.org/content/12/19_Supplement/B35 | http://ascopubs.org/doi/abs/10.1200/jco.2008.26.15_suppl.1055

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Tyrosine-protein kinase receptor FLT3 42 Target ID: CHEMBL1974 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25896848 \| http://adisinsight.springer.com/drugs/800007613	Inhibitor 8504
DNA topoisomerase 2 5 Target ID: P06786 Gene ID: 855636.0 Gene Symbol: TOP2 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8622625	Inhibitor 8504	8.0 nM [IC50]
UDP-glucuronosyltransferase 1-10 2 Target ID: CHEMBL1743320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22659092	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18828924 DOI: 10.1200/jco.2008.26.15_suppl.1055	Primary	Phase II 1147	Unknown Approved Use Unknown
Advanced solid cancer 30 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20031390	Primary	Phase I 438	Unknown Approved Use Unknown
Colorectal cancer 102 Sources: http://www.oxbio.com/pressreleases/011706_Xanthus.pdf https://www.ncbi.nlm.nih.gov/pubmed/18073154	Primary	Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
640 mg/m2 1 times / week multiple, intravenous MTD Dose: 640 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 640 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/20031390	unhealthy Health Status: unhealthy Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20031390	DLT: neutropaenia... Dose limiting toxicities: neutropaenia (grade 4, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/20031390

AEs

AE	Significance	Dose	Population
neutropaenia	grade 4, 2 patients DLT	640 mg/m2 1 times / week multiple, intravenous MTD Dose: 640 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 640 mg/m2, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/20031390	unhealthy Health Status: unhealthy Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20031390

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM138154399	http://www.alfa-chemistry.com/search.aspx?q=ACM138154399
BOC Sciences	138154-39-9	http://www.bocsci.com/description.asp?cas=138154-39-9
Lan Pharmatech	LQT-B48902
MuseChem	I007279	https://www.musechem.com/product/I007279.html
MuseChem	I014696	https://www.musechem.com/product/I014696.html
Norris Pharm	NSZB-A281072

PubMed

Title	Date	PubMed
Pharmaceutical development of a parenteral lyophilised dosage form for the novel anticancer agent C1311.	2005-12-01	16316064
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.	2005-09-01	15899571
Cell killing by the novel imidazoacridinone antineoplastic agent, C-1311, is inhibited at high concentrations coincident with dose-differentiated cell cycle perturbation.	1996-11	8912530
Chromophore-modified antineoplastic imidazoacridinones. Synthesis and activity against murine leukemias.	1992-01-24	1732555
5-[(Aminoalkyl)amino]imidazo[4,5,1-de]acridin-6-ones as a novel class of antineoplastic agents. Synthesis and biological activity.	1990-01	2296035

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:57:22 GMT 2025` Edited by `admin` on `Mon Mar 31 18:57:22 GMT 2025`
Record UNII	MZ4Y5H4OAB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

C-1311

Common Name

English

NSC-645809

Preferred Name

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

DTXSID10160508