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 230.6933
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINACRINE HYDROCHLORIDE

SMILES

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

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

Molecular Formula ClH
Molecular Weight 36.4609
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
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
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
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
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
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
Studies of the toxicological potential of tripeptides (L-valyl-L-prolyl-L-proline and L-isoleucyl-L-prolyl-L-proline): IX. Evaluation of the mutagenic potential of synthesized L-valyl-L-prolyl-L-proline in the Salmonella-Escherichia coli/microsome, incorporation assay.
2005
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
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
Study on the inclusion behavior of p-sulphonatocalix[4]arene with 9-amino-acridine by spectrofluorometric titrations.
2006 Feb
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
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
Flow cytometric detection of tandem repeat mutations induced by various chemical classes.
2006 Jun 25
Frameshift mutations induced by four isomeric nitroacridines and their des-nitro counterpart in the lacZ reversion assay in Escherichia coli.
2006 Mar
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
Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions.
2007 Jul 6
The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine).
2007 Oct
In silico chemical library screening and experimental validation of a novel 9-aminoacridine based lead-inhibitor of human S-adenosylmethionine decarboxylase.
2007 Sep-Oct
New palladium(II) and platinum(II) complexes with 9-aminoacridine: structures, luminiscence, theoretical calculations, and antitumor activity.
2008 Aug 4
Biological safety of liposome-fullerene consisting of hydrogenated lecithin, glycine soja sterols, and fullerene-C60 upon photocytotoxicity and bacterial reverse mutagenicity.
2009 Apr
Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates.
2009 Apr 1
Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.
2009 Jan 22
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
Alveolar osteitis: a comprehensive review of concepts and controversies.
2010
Host hindrance to HIV-1 replication in monocytes and macrophages.
2010 Apr 7
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
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 13:13:43 UTC 2021
Edited
by admin
on Sat Jun 26 13:13:43 UTC 2021
Record UNII
OR5RM3Q5QL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMINACRINE HYDROCHLORIDE
HSDB   MI   USAN   VANDF  
USAN  
Official 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
AMINOACRIDINE HYDROCHLORIDE [WHO-DD]
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 Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
NCI_THESAURUS C28394
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
EPA PESTICIDE CODE 55503
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
Code System Code Type Description
EVMPD
SUB00450MIG
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
PUBCHEM
8643
Created by admin on Sat Jun 26 13:13:44 UTC 2021 , Edited by admin on Sat Jun 26 13:13:44 UTC 2021
PRIMARY
CAS
134-50-9
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-145-5
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
MERCK INDEX
M1672
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY Merck Index
RXCUI
81949
Created by admin on Sat Jun 26 13:13:44 UTC 2021 , Edited by admin on Sat Jun 26 13:13:44 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C77024
Created by admin on Sat Jun 26 13:13:44 UTC 2021 , Edited by admin on Sat Jun 26 13:13:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL43184
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
FDA UNII
OR5RM3Q5QL
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
EPA CompTox
134-50-9
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
HSDB
4505
Created by admin on Sat Jun 26 13:13:43 UTC 2021 , Edited by admin on Sat Jun 26 13:13:43 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY