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Details

Stereochemistry ACHIRAL
Molecular Formula C13H10N2
Molecular Weight 194.2324
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINACRINE

SMILES

c1ccc2c(c1)c(=N)c3ccccc3[nH]2

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

Molecular Formula C13H10N2
Molecular Weight 194.2324
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
A phase I trial of amsalog (CI-921) administered by intravenous infusion using a 5-day schedule.
2001 Apr
[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
Putative identification of functional interactions between DNA intercalating agents and topoisomerase II using the V79 in vitro micronucleus assay.
2002 Jun 19
Bead injection for surface enhanced Raman spectroscopy: automated on-line monitoring of substrate generation and application in quantitative analysis.
2002 Oct
Frameshift mutations induced by three classes of acridines in the lacZ reversion assay in Escherichia coli: potency of responses and relationship to slipped mispairing models.
2003
Interaction of antitumoral 9-aminoacridine drug with DNA and dextran sulfate studied by fluorescence and surface-enhanced Raman spectroscopy.
2003
Lipid membrane with low proton permeability.
2003 Apr 1
9-Aminoacridine: an efficient reagent to improve human and plant chromosome banding patterns and to standardize chromosome image analysis.
2003 Jan
The metabolism of aluminum citrate and biosynthesis of oxalic acid in Pseudomonas fluorescens.
2003 Jul
Synthesis, characterization, and photophysical studies of new bichromophoric ruthenium(II) complexes.
2003 Mar 10
On-line monitoring of airborne chemistry in levitated nanodroplets: in situ synthesis and application of SERS-active Ag-Sols for trace analysis by FT-Raman spectroscopy.
2003 May 1
Ascorbate in thylakoid lumen functions as an alternative electron donor to photosystem II and photosystem I.
2004 Sep 1
Excited-state intramolecular charge transfer in 9-aminoacridine derivative.
2005 Jul 14
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Study on the inclusion behavior of p-sulphonatocalix[4]arene with 9-amino-acridine by spectrofluorometric titrations.
2006 Feb
In vitro and in vivo anti-retroviral activity of the substance purified from the aqueous extract of Chelidonium majus L.
2006 Nov
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
Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions.
2007 Jul 6
Molecular recognition of DNA by rigid [N]-polynorbornane-derived bifunctional intercalators: synthesis and evaluation of their binding properties.
2007 May 17
The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine).
2007 Oct
Ultrasonic trapping of microparticles in suspension and reaction monitoring using Raman microspectroscopy.
2007 Oct 15
In silico chemical library screening and experimental validation of a novel 9-aminoacridine based lead-inhibitor of human S-adenosylmethionine decarboxylase.
2007 Sep-Oct
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
New palladium(II) and platinum(II) complexes with 9-aminoacridine: structures, luminiscence, theoretical calculations, and antitumor activity.
2008 Aug 4
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
Matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of cellular glycerophospholipids enabled by multiplexed solvent dependent analyte-matrix interactions.
2008 Oct 1
Phosphatidylcholines and -ethanolamines can be easily mistaken in phospholipid mixtures: a negative ion MALDI-TOF MS study with 9-aminoacridine as matrix and egg yolk as selected example.
2009 Dec
Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II.
2009 Jan 14
Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.
2009 Jan 22
Biological safety of LipoFullerene composed of squalane and fullerene-C60 upon mutagenesis, photocytotoxicity, and permeability into the human skin tissue.
2009 Jun
Investigation on the Interactions of NiCR and NiCR-2H with DNA.
2010
Alveolar osteitis: a comprehensive review of concepts and controversies.
2010
Host hindrance to HIV-1 replication in monocytes and macrophages.
2010 Apr 7
The intact muscle lipid composition of bulls: an investigation by MALDI-TOF MS and 31P NMR.
2010 Feb
Genotoxicity and antigenotoxicity evaluation of non-photoactivated hypericin.
2010 Jan
Lipidomic analysis of porcine olfactory epithelial membranes and cilia.
2010 Jul
Mutagenic and antimutagenic effects of hexane extract of some Astragalus species grown in the eastern Anatolia region of Turkey.
2010 Jul
Significant sensitivity improvements by matrix optimization: a MALDI-TOF mass spectrometric study of lipids from hen egg yolk.
2010 Jun
Selective desorption/ionization of sulfatides by MALDI-MS facilitated using 9-aminoacridine as matrix.
2010 Jun
Modulation of mdm2 pre-mRNA splicing by 9-aminoacridine-PNA (peptide nucleic acid) conjugates targeting intron-exon junctions.
2010 Jun 30
The surface charge density of plant cell membranes (sigma): an attempt to resolve conflicting values for intrinsic sigma.
2010 May
Molecular docking studies of selected tricyclic and quinone derivatives on trypanothione reductase of Leishmania infantum.
2010 Oct
MALDI-TOF/MS analysis of archaebacterial lipids in lyophilized membranes dry-mixed with 9-aminoacridine.
2010 Sep
Mononuclear Fe(II)-N4Py complexes in oxidative DNA cleavage: structure, activity and mechanism.
2010 Sep 14
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:09:59 UTC 2021
Edited
by admin
on Sat Jun 26 00:09:59 UTC 2021
Record UNII
78OY3Z0P7Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMINACRINE
MI   VANDF  
Common Name English
9-ACRIDINAMINE
Systematic Name English
NSC-13000
Code English
AMINOACRIDINE [WHO-DD]
Common Name 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 Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
NCI_THESAURUS C28394
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
WHO-VATC QD08AA02
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
201-995-6
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
FDA UNII
78OY3Z0P7Z
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
RXCUI
645
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY RxNorm
EPA CompTox
90-45-9
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
DRUG BANK
DB11561
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
INN
1476
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
MERCK INDEX
M1672
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
9-AMINOACRIDINE
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
DRUG CENTRAL
160
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL43184
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
CAS
90-45-9
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
EVMPD
SUB05437MIG
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
PUBCHEM
7019
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
NCI_THESAURUS
C77023
Created by admin on Sat Jun 26 00:09:59 UTC 2021 , Edited by admin on Sat Jun 26 00:09:59 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY