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Details

Stereochemistry ACHIRAL
Molecular Formula C18H20N4O2.2ClH.H2O
Molecular Weight 415.314
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITRACRINE DIHYDROCHLORIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=NHZMLGQMVDPHND-UHFFFAOYSA-N
InChI=1S/C18H20N4O2.2ClH.H2O/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);2*1H;1H2

HIDE SMILES / InChI
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
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.
Name Type Language
NITRACRINE DIHYDROCHLORIDE MONOHYDRATE
MI  
Common Name English
9-(3-((DIMETHYLAMINO)PROPYL)AMINO)-1-NITROACRIDINE DIHYDROCHLORIDE MONOHYDRATE
Systematic Name English
LEDAKRIN
Brand Name English
NITRACRINE DIHYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
1,3-PROPANEDIAMINE, N1,N1-DIMETHYL-N3-(1-NITRO-9-ACRIDINYL)-, HYDROCHLORIDE, HYDRATE (1:2:1)
Systematic Name English
C-283
Code English
Code System Code Type Description
CAS
55429-45-3
Created by admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
PRIMARY
FDA UNII
7G5S4303OI
Created by admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
PRIMARY
MERCK INDEX
m7927
Created by admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
PRIMARY Merck Index
PUBCHEM
72941568
Created by admin on Sat Dec 16 11:11:04 GMT 2023 , Edited by admin on Sat Dec 16 11:11:04 GMT 2023
PRIMARY