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
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)
DescriptionCurator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/23841224
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).
Originator
Approval Year
Doses
| Dose | Population | Adverse 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) Sources: allantoin(140 mg; 2/day) |
unhealthy, adult n = 51 Health Status: unhealthy Condition: trichomoniasis Age Group: adult Sex: F Population Size: 51 Sources: |
Other AEs: Vulvovaginal discomfort... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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) Sources: allantoin(140 mg; 2/day) |
unhealthy, adult n = 51 Health Status: unhealthy Condition: trichomoniasis Age Group: adult Sex: F Population Size: 51 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Excited-state intramolecular charge transfer in 9-aminoacridine derivative. | 2005 Jul 14 |
|
| Acridin-9-yl exchange: a proposal for the action of some 9-aminoacridine drugs. | 2006 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity. | 2007 |
|
| Analysis of low molecular weight acids by negative mode matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 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 |
|
| 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 |
|
| The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine). | 2007 Oct |
|
| A role of the 9-aminoacridines and their conjugates in a life science. | 2007 Oct |
|
| 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 |
|
| 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 |
|
| Effect of spermine conjugation on the interaction of acridine with alternating purine-pyrimidine oligodeoxyribonucleotides studied by CD, fluorescence and absorption spectroscopies. | 2008 Apr |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Blockade of NMDA receptor channels by 9-aminoacridine and its derivatives. | 2009 Feb 13 |
|
| In situ primary metabolites localization on a rat brain section by chemical mass spectrometry imaging. | 2009 Jul 1 |
|
| 9-Aminoacridine inhibition of HIV-1 Tat dependent transcription. | 2009 Jul 24 |
|
| Biological safety of LipoFullerene composed of squalane and fullerene-C60 upon mutagenesis, photocytotoxicity, and permeability into the human skin tissue. | 2009 Jun |
|
| Identification of chemical compounds that induce HIF-1alpha activity. | 2009 Nov |
|
| 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 |
|
| 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
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
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WHO-ATC |
D08AA02
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NCI_THESAURUS |
C28394
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WHO-VATC |
QD08AA02
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201-995-6
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78OY3Z0P7Z
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645
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13000
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DTXSID2024456
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DB11561
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M1672
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9-AMINOACRIDINE
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160
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51803
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CHEMBL43184
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90-45-9
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SUB05437MIG
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74789
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7019
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C77023
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
