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
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
| 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 |
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 |
|---|---|---|
| Effects of DNA structure on oxopropenylation by the endogenous mutagens malondialdehyde and base propenal. | 2002 Apr 16 |
|
| 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 |
|
| 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 |
|
| Superior duplex DNA strand invasion by acridine conjugated peptide nucleic acids. | 2003 May 28 |
|
| 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 |
|
| 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 |
|
| Platinum-acridinylthiourea conjugates show cell line-specific cytotoxic enhancement in H460 lung carcinoma cells compared to cisplatin. | 2005 Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Frameshift mutations produced by 9-aminoacridine in wild-type, uvrA and recA strains of Escherichia coli; specificity within a hotspot. | 2007 Sep |
|
| 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 |
|
| 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 |
|
| Blockade of NMDA receptor channels by 9-aminoacridine and its derivatives. | 2009 Feb 13 |
|
| 9-Aminoacridine-based anticancer drugs target the PI3K/AKT/mTOR, NF-kappaB and p53 pathways. | 2009 Feb 26 |
|
| Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials. | 2009 Jan 22 |
|
| In situ primary metabolites localization on a rat brain section by chemical mass spectrometry imaging. | 2009 Jul 1 |
|
| 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 |
|
| 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 |
|
| Genotoxicity and antigenotoxicity evaluation of non-photoactivated hypericin. | 2010 Jan |
|
| 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 |
|
| Molecular docking studies of selected tricyclic and quinone derivatives on trypanothione reductase of Leishmania infantum. | 2010 Oct |
|
| 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
| Substance Class |
Chemical
Created
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admin
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Wed Jul 05 22:58:56 UTC 2023
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| Record UNII |
OR5RM3Q5QL
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Validated (UNII)
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CFR |
21 CFR 310.531
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C28394
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55503
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |