U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C13H10N2
Molecular Weight 194.2319
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
Effects of slow clinorotation on lipid contents and proton permeability of thylakoid membranes of pea chloroplasts.
2001
Potentiation of BCNU cytotoxicity by molecules targeting abasic lesions in DNA.
2001 Jul
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
Putative identification of functional interactions between DNA intercalating agents and topoisomerase II using the V79 in vitro micronucleus assay.
2002 Jun 19
Blocker studies of the functional architecture of the NMDA receptor channel.
2002 Mar-Apr
Bead injection for surface enhanced Raman spectroscopy: automated on-line monitoring of substrate generation and application in quantitative analysis.
2002 Oct
Aminoglycoside (neomycin) preference is for A-form nucleic acids, not just RNA: results from a competition dialysis study.
2003 Aug 27
9-Aminoacridine: an efficient reagent to improve human and plant chromosome banding patterns and to standardize chromosome image analysis.
2003 Jan
Superior duplex DNA strand invasion by acridine conjugated peptide nucleic acids.
2003 May 28
Determinants of trapping block of N-methyl-d-aspartate receptor channels.
2003 Oct
RNA-ligand interactions: affinity and specificity of aminoglycoside dimers and acridine conjugates to the HIV-1 Rev response element.
2003 Oct 7
Enhancement of plasmid curing by 9-aminoacridine and two phenothiazines in the presence of proton pump inhibitor 1-(2-benzoxazolyl)-3,3,3-trifluoro-2-propanone.
2003 Sep
Chloroplast mutations induced by 9-aminoacridine hydrochloride are independent of the plastome mutator in Oenothera.
2004 Feb
Anti-stress activity of Propionibacterium freudenreichii : identification of a reactivative protein.
2004 Jan
Antigenotoxic potential of glucomannan on four model test systems.
2004 Nov
Ascorbate in thylakoid lumen functions as an alternative electron donor to photosystem II and photosystem I.
2004 Sep 1
Acridine derivatives activate p53 and induce tumor cell death through Bax.
2005 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Characterization of a nonphotochemical quenching-deficient Arabidopsis mutant possessing an intact PsbS protein, xanthophyll cycle and lumen acidification.
2006 Feb
Synthesis, anti-inflammatory, analgesic and kinase (CDK-1, CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff's bases.
2006 Jun 1
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
Discriminating between cellular and misfolded prion protein by using affinity to 9-aminoacridine compounds.
2007 Apr
The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine).
2007 Oct
Modulation of the genotoxicity of bleomycin by amines through noncovalent DNA interactions and alteration of physiological conditions in yeast.
2007 Oct 1
Ultrasonic trapping of microparticles in suspension and reaction monitoring using Raman microspectroscopy.
2007 Oct 15
Frameshift mutations produced by 9-aminoacridine in wild-type, uvrA and recA strains of Escherichia coli; specificity within a hotspot.
2007 Sep
Effect of spermine conjugation on the interaction of acridine with alternating purine-pyrimidine oligodeoxyribonucleotides studied by CD, fluorescence and absorption spectroscopies.
2008 Apr
Biological safety of liposome-fullerene consisting of hydrogenated lecithin, glycine soja sterols, and fullerene-C60 upon photocytotoxicity and bacterial reverse mutagenicity.
2009 Apr
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
9-Aminoacridine inhibition of HIV-1 Tat dependent transcription.
2009 Jul 24
Binding of TCA to the prion protein: mechanism, implication for therapy, and application as probe for complex formation of bio-macromolecules.
2009 Oct
A kinetic and structural investigation of DNA-based asymmetric catalysis using first-generation ligands.
2009 Sep 21
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
Selective desorption/ionization of sulfatides by MALDI-MS facilitated using 9-aminoacridine as matrix.
2010 Jun
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:22:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:30 GMT 2023
Record UNII
78OY3Z0P7Z
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
WHO-VATC QD08AA02
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
201-995-6
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
FDA UNII
78OY3Z0P7Z
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
RXCUI
645
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY RxNorm
NSC
13000
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID2024456
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
DRUG BANK
DB11561
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
INN
1476
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
SMS_ID
100000087206
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
MERCK INDEX
m1672
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
9-AMINOACRIDINE
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
DRUG CENTRAL
160
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
CHEBI
51803
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL43184
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
CAS
90-45-9
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
EVMPD
SUB05437MIG
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
CHEBI
74789
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
PUBCHEM
7019
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
NCI_THESAURUS
C77023
Created by admin on Fri Dec 15 15:22:30 GMT 2023 , Edited by admin on Fri Dec 15 15:22:30 GMT 2023
PRIMARY
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