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Details

Stereochemistry ACHIRAL
Molecular Formula C13H10N2
Molecular Weight 194.2319
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINACRINE

SMILES

NC1=C2C=CC=CC2=NC3=C1C=CC=C3

InChI

InChIKey=XJGFWWJLMVZSIG-UHFFFAOYSA-N
InChI=1S/C13H10N2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H,(H2,14,15)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/23841224

Aminacrine has long been known to be a potent frameshift mutagen in viruses and bacteria. It is one in a general class of aminoacridine dyes that bind to DNA and possess mutagenic activity. Aminacrine is used clinically as a topical antiseptic. A part from therapeutic use, aminacrine is also introduced as a matrix for negative mode matrix-assisted laser desorption/ionization (MALDI).

Approval Year

Conditions

Conditions

Doses

Doses

DosePopulationAdverse events​
14 mg 2 times / day multiple, vaginal
Recommended
Dose: 14 mg, 2 times / day
Route: vaginal
Route: multiple
Dose: 14 mg, 2 times / day
Co-administed with::
sulfanilamide(1.05 g; 2/day)
allantoin(140 mg; 2/day)
Sources:
unhealthy, adult
n = 51
Health Status: unhealthy
Condition: trichomoniasis
Age Group: adult
Sex: F
Population Size: 51
Sources:
Other AEs: Vulvovaginal discomfort...
Other AEs:
Vulvovaginal discomfort (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Vulvovaginal discomfort 2 patients
14 mg 2 times / day multiple, vaginal
Recommended
Dose: 14 mg, 2 times / day
Route: vaginal
Route: multiple
Dose: 14 mg, 2 times / day
Co-administed with::
sulfanilamide(1.05 g; 2/day)
allantoin(140 mg; 2/day)
Sources:
unhealthy, adult
n = 51
Health Status: unhealthy
Condition: trichomoniasis
Age Group: adult
Sex: F
Population Size: 51
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Synthesis and antibacterial activity of the new 9-aminoacridine, 10,11-dihydro-5H-dibenzo[b,f]azepine, polyfluoro 5,6-dihydro-1,3,5-oxadiazine derivatives].
2001
Effects of slow clinorotation on lipid contents and proton permeability of thylakoid membranes of pea chloroplasts.
2001
Surface-enhanced Raman and steady fluorescence study of interaction between antitumoral drug 9-aminoacridine and trypsin-like protease related to metastasis processes, guanidinobenzoatase.
2001
[Extracellular protein of propionic acid bacteria inhibits induced mutation in strains of Salmonella typhimurium].
2001 Jan-Feb
Potentiation of BCNU cytotoxicity by molecules targeting abasic lesions in DNA.
2001 Jul
Cytochrome b(6)f mutation specifically affects thermal dissipation of absorbed light energy in Arabidopsis.
2001 Nov
Influence of polyamine architecture on the transport and topoisomerase II inhibitory properties of polyamine DNA-intercalator conjugates.
2001 Oct 25
Effects of DNA structure on oxopropenylation by the endogenous mutagens malondialdehyde and base propenal.
2002 Apr 16
A study of amsalog (CI-921) administered orally on a 5-day schedule, with bioavailability and pharmacokinetically guided dose escalation.
2002 Jan
Anacardic acid-mediated changes in membrane potential and pH gradient across liposomal membranes.
2002 Jan 2
Putative identification of functional interactions between DNA intercalating agents and topoisomerase II using the V79 in vitro micronucleus assay.
2002 Jun 19
Synthesis, characterization, and photophysical studies of new bichromophoric ruthenium(II) complexes.
2003 Mar 10
Determinants of trapping block of N-methyl-d-aspartate receptor channels.
2003 Oct
Antigenotoxic potential of glucomannan on four model test systems.
2004 Nov
Endoreduplication induced in cultured Chinese hamster cells by different anti-topoisomerase II chemicals. Evidence for the essential contribution of the enzyme to chromosome segregation.
2005 Apr 4
Acridine derivatives activate p53 and induce tumor cell death through Bax.
2005 Aug
An investigation of DNA mismatch repair capacity under normal culture conditions and under conditions of supra-physiological challenge in human CD4+T cell clones from donors of different ages.
2005 Dec
Excited-state intramolecular charge transfer in 9-aminoacridine derivative.
2005 Jul 14
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Platinum-acridinylthiourea conjugates show cell line-specific cytotoxic enhancement in H460 lung carcinoma cells compared to cisplatin.
2005 Oct
High-performance liquid chromatography-mass spectrometry-based acetylcholinesterase assay for the screening of inhibitors in natural extracts.
2006 Apr 21
Characterization of a nonphotochemical quenching-deficient Arabidopsis mutant possessing an intact PsbS protein, xanthophyll cycle and lumen acidification.
2006 Feb
Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum.
2006 Jan 15
New peptide conjugates with 9-aminoacridine: synthesis and binding to DNA.
2006 Jul
Photoinduced intramolecular charge transfer in 9-aminoacridinium derivatives assisted by intramolecular H-bond.
2006 Jun 22
Frameshift mutations induced by four isomeric nitroacridines and their des-nitro counterpart in the lacZ reversion assay in Escherichia coli.
2006 Mar
Synergistic interaction between proton pump inhibitors and resistance modifiers: promoting effects of antibiotics and plasmid curing.
2006 May-Jun
Structure-activity relationship study of 9-aminoacridine compounds in scrapie-infected neuroblastoma cells.
2006 Sep 15
Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity.
2007
Discriminating between cellular and misfolded prion protein by using affinity to 9-aminoacridine compounds.
2007 Apr
A real-time fluorescence assay for measuring N-dealkylation.
2007 Jan
A binary matrix for background suppression in MALDI-MS of small molecules.
2007 Mar
Molecular recognition of DNA by rigid [N]-polynorbornane-derived bifunctional intercalators: synthesis and evaluation of their binding properties.
2007 May 17
Negative ion mode matrix-assisted laser desorption/ionisation time-of-flight mass spectrometric analysis of oligosaccharides using halide adducts and 9-aminoacridine matrix.
2008 Apr
Drug 9AA reactivates p21/Waf1 and Inhibits HIV-1 progeny formation.
2008 Mar 18
Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage.
2008 May 15
Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II.
2009 Jan 14
Investigation on the Interactions of NiCR and NiCR-2H with DNA.
2010
Host hindrance to HIV-1 replication in monocytes and macrophages.
2010 Apr 7
The surface charge density of plant cell membranes (sigma): an attempt to resolve conflicting values for intrinsic sigma.
2010 May
MALDI-TOF/MS analysis of archaebacterial lipids in lyophilized membranes dry-mixed with 9-aminoacridine.
2010 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Vaginal suppositories containing 1.05 g of sulfanilamide, 14 mg of aminacrine hydrochloride, and 140 mg of allantoin (AVC suppositories) were given twice a day for 7 days.
Route of Administration: Vaginal
In Vitro Use Guide
S. typhimurium cells were treated with aminacrine at concentration of 2-250 ug/ml and incubated during 60 min.
Name Type Language
AMINACRINE
MI   VANDF  
Common Name English
9-ACRIDINAMINE
Systematic Name English
Aminoacridine [WHO-DD]
Common Name English
NSC-13000
Code English
AMINACRINE [MI]
Common Name English
AMINACRINE [VANDF]
Common Name English
aminoacridine [INN]
Common Name English
9-AMINOACRIDINE
Systematic Name English
ACRIDIN-9-AMINE
Systematic Name English
AMINOACRIDINE
INN   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
WHO-ATC D08AA02
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
NCI_THESAURUS C28394
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
WHO-VATC QD08AA02
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
201-995-6
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
FDA UNII
78OY3Z0P7Z
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
RXCUI
645
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY RxNorm
NSC
13000
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID2024456
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
DRUG BANK
DB11561
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
INN
1476
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
SMS_ID
100000087206
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
MERCK INDEX
M1672
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
9-AMINOACRIDINE
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
DRUG CENTRAL
160
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
CHEBI
51803
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
ChEMBL
CHEMBL43184
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
CAS
90-45-9
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
EVMPD
SUB05437MIG
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
CHEBI
74789
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
PUBCHEM
7019
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY
NCI_THESAURUS
C77023
Created by admin on Wed Jul 05 22:53:00 UTC 2023 , Edited by admin on Wed Jul 05 22:53:00 UTC 2023
PRIMARY