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

Details

Stereochemistry ACHIRAL
Molecular Formula C13H10N2.ClH
Molecular Weight 230.693
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINACRINE HYDROCHLORIDE

SMILES

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

InChI

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

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

Molecular Formula ClH
Molecular Weight 36.461
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
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
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
Aminoglycoside (neomycin) preference is for A-form nucleic acids, not just RNA: results from a competition dialysis study.
2003 Aug 27
Superior duplex DNA strand invasion by acridine conjugated peptide nucleic acids.
2003 May 28
A transient product of DNA alkylation can be stabilized by binding localization.
2003 Nov 19
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
Anti-stress activity of Propionibacterium freudenreichii : identification of a reactivative protein.
2004 Jan
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
Acridin-9-yl exchange: a proposal for the action of some 9-aminoacridine drugs.
2006
Study on the inclusion behavior of p-sulphonatocalix[4]arene with 9-amino-acridine by spectrofluorometric titrations.
2006 Feb
Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum.
2006 Jan 15
Cellular delivery of polyheteroaromate-peptide nucleic acid conjugates mediated by cationic lipids.
2006 Jan-Feb
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
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
Analysis of low molecular weight acids by negative mode matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2007
Quantitative detection of metabolites using matrix-assisted laser desorption/ionization mass spectrometry with 9-aminoacridine as the matrix.
2007
Imaging Matrix Assisted Laser Desorption Ionization Mass Spectrometry: a technique to map plant metabolites within tissues at high spatial resolution.
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
Preparation of magnetite nanocrystals with surface reactive moieties by one-pot reaction.
2007 Jul 15
Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions.
2007 Jul 6
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
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
In silico chemical library screening and experimental validation of a novel 9-aminoacridine based lead-inhibitor of human S-adenosylmethionine decarboxylase.
2007 Sep-Oct
Effect of spermine conjugation on the interaction of acridine with alternating purine-pyrimidine oligodeoxyribonucleotides studied by CD, fluorescence and absorption spectroscopies.
2008 Apr
Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage.
2008 May 15
Blockade of NMDA receptor channels by 9-aminoacridine and its derivatives.
2009 Feb 13
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
Binding of TCA to the prion protein: mechanism, implication for therapy, and application as probe for complex formation of bio-macromolecules.
2009 Oct
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 15:29:09 GMT 2023
Edited
by admin
on Fri Dec 15 15:29:09 GMT 2023
Record UNII
OR5RM3Q5QL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMINACRINE HYDROCHLORIDE
HSDB   MI   USAN   VANDF  
USAN  
Official Name English
Aminoacridine hydrochloride [WHO-DD]
Common Name English
AMINACRINE HYDROCHLORIDE [VANDF]
Common Name English
MONACRIN
Brand Name English
AMINOACRIDINE HYDROCHLORIDE
MART.   WHO-DD  
Systematic Name English
NSC-7571
Code English
AMINACRINE HYDROCHLORIDE [MI]
Common Name English
AMINACRINE HYDROCHLORIDE [USAN]
Common Name English
AMINOACRIDINE HCL
Common Name English
AMINOACRIDINE HYDROCHLORIDE [MART.]
Common Name English
9-ACRIDINAMINE MONOHYDROCHLORIDE
Systematic Name English
AMINACRINE HYDROCHLORIDE [HSDB]
Common Name English
AMINACRINE HCL
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.531
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
EPA PESTICIDE CODE 55503
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
Code System Code Type Description
EVMPD
SUB00450MIG
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
PUBCHEM
8643
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
NSC
7571
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
CAS
134-50-9
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-145-5
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
MERCK INDEX
m1672
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY Merck Index
RXCUI
81949
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C77024
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
SMS_ID
100000085173
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL43184
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
FDA UNII
OR5RM3Q5QL
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID8030473
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
CHEBI
74837
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
HSDB
4505
Created by admin on Fri Dec 15 15:29:09 GMT 2023 , Edited by admin on Fri Dec 15 15:29:09 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY