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Details

Stereochemistry ACHIRAL
Molecular Formula C18H20N4O2
Molecular Weight 324.377
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITRACRINE

SMILES

CN(C)CCCNC1=C2C=CC=CC2=NC3=C1C(=CC=C3)[N+]([O-])=O

InChI

InChIKey=YMVWGSQGCWCDGW-UHFFFAOYSA-N
InChI=1S/C18H20N4O2/c1-21(2)12-6-11-19-18-13-7-3-4-8-14(13)20-15-9-5-10-16(17(15)18)22(23)24/h3-5,7-10H,6,11-12H2,1-2H3,(H,19,20)

HIDE SMILES / InChI

Molecular Formula C18H20N4O2
Molecular Weight 324.377
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Nitracrine (Ledakrin, C-283) is an acridine derivative with potential cytostatic and antitumor activities. Nitracrine induces the unwinding of supercoiled DNA and binds to the DNA through intercalation, forming drug-DNA adducts and DNA interstrand crosslinks. This inhibits RNA synthesis, protein production, cell growth, DNA replication and cell proliferation; altogether, this may promote apoptosis. Since cancer cells have increased metabolism and proliferate at an increased rate, nitracrine may induce tumor cell apoptosis. The drug was used in clinics in Poland for the treatment of ovarian, colon, lung and mammary carcinomas. Some undesirable effects observed in clinics: e.g. nausea, vomiting and toxicity and mutagenicity of the drug in S. typhimurium strongly limited the therapeutic use of nitracrine and promoted a search for more suitable analogues.

CNS Activity

Curator's Comment: The lack of bone marrow toxicity and the poor penetration of the central nervous system by nitracrine are attractive features of the drug.

Originator

Curator's Comment: Nitracrine belongs to a group of several hundred acridine derivatives synthesized by the group formerly led in Gdansk (Poland) by Zygmunt Ledochowski and then by Andrzej Ledoehowski.

Approval Year

PubMed

PubMed

TitleDatePubMed
Preclinical pharmacologic studies on 1-nitro-9-(dimethylaminopropylamino)-acridine and its n-oxide. II. Chronic action.
1972
Preclinical pharmacologic investigations on 1-nitro-9-(dimethylaminopropylamino)-acridine and its N-oxide. I. Acute and subchronic activity.
1972
Ledakrin--anticancerous medicine 1-nitro-9(3-dimethylaminopropylamino)-acridine -2HCl-H2O.
1976 Jul-Sep
Selective toxicity of nitracrine to hypoxic mammalian cells.
1984 Feb
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
1989 Jan
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
1989 Jan
Patents

Patents

Sample Use Guides

In Vitro Use Guide
Nitracrine displayed slective toxicity towards hypoxic AA8 cells, with a pronounced differential between killing of aerobic and hypoxic cells at a concentration of 0.1 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:05:09 GMT 2023
Edited
by admin
on Sat Dec 16 16:05:09 GMT 2023
Record UNII
712MLZ30SB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NITRACRINE
INN   MI  
INN  
Official Name English
NITRACRINE [MI]
Common Name English
nitracrine [INN]
Common Name English
9-((3-(DIMETHYLAMINO)PROPYL)AMINO)-1-NITROACRIDINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C582
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
Code System Code Type Description
DRUG CENTRAL
3386
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
NCI_THESAURUS
C694
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
EVMPD
SUB09314MIG
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
MERCK INDEX
m7927
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY Merck Index
INN
3916
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
CAS
4533-39-5
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
SMS_ID
100000083892
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
FDA UNII
712MLZ30SB
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID90196481
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
PUBCHEM
20628
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL26291
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
MESH
D009564
Created by admin on Sat Dec 16 16:05:09 GMT 2023 , Edited by admin on Sat Dec 16 16:05:09 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY