AMINACRINE

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 Search

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

Description
Sources: http://www.pnas.org/content/74/1/188.full.pdf
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

Conditions

Condition	Modality	Highest Phase	Product
Mycoses 12 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=012470	Curative	Approved 8429	AKRINOL Approved Use Antifungal agent
Vaginal trichomoniasis 9 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9132982	Curative	Phase I 428	Unknown Approved Use Unknown
Adult T-cell leukemia/lymphoma 5 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4060757/pdf/1742-4690-11-43.pdf	Primary	Basic research	Unknown Approved Use Unknown

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) allantoin(140 mg; 2/day) Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/	unhealthy, adult n = 51 Health Status: unhealthy Condition: trichomoniasis Age Group: adult Sex: F Population Size: 51 Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/	Other AEs: Vulvovaginal discomfort... Other AEs: Vulvovaginal discomfort (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/

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) allantoin(140 mg; 2/day) Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/	unhealthy, adult n = 51 Health Status: unhealthy Condition: trichomoniasis Age Group: adult Sex: F Population Size: 51 Sources: https://pubmed.ncbi.nlm.nih.gov/9132982/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY454464	https://www.001chemical.com/chem/90-45-9
3B Scientific (Wuhan) Corp	3B3-019151	http://www.3bsc.com/index/pro_info.php?id=41675
AA Blocks	AA00GRHV	http://www.aablocks.com/goods/Goods/detail?id=AA00GRHV
AEchem Scientific Corp., USA	AE021949	http://www.aechemsc.com/info_products/AE021949.php
AHH Chemical co.,ltd	MT-46290	http://www.ahhchemical.com/product/MT-46290.html
AK Scientific, Inc. (AKSCI)	U978	http://www.aksci.com/item_detail.php?cat=U978
Aaron Chemicals	AR00GS9N	http://www.aaronchem.com/90-45-9
AbMole Bioscience	M3179	http://www.abmole.com/products/9-aminoacridine.html
Acadechem	ACDS-033467	http://www.acadechemical.com/product/108166
Accela ChemBio Inc	SY039786	http://www.accelachem.com/cn/search.html?keyword=SY039786&attname=GoodsCode
Achemica	ACMC-20mczt	http://www.achemica.com/prodinfo/?id=198255
Achemo Scientific Limited	AC-81344	http://www.achemo.com/search/?Keyword= 90-45-9
Achemtek	0104-017002	http://www.achemtek.com/90-45-9
Alfa Chemistry	ACM90459	https://materials.alfachemic.com/cas_90-45-9.htm
Alfa Chemistry	AP90459	https://reagents.alfa-chemistry.com/product/9-aminoacridine-cas-90-45-9-18378.html
Alichem	449041850	http://www.alichem.com/en/products/90-45-9.html
Alinda	ALBB-020726	http://alinda.ru/finechem_en_.html?i=ALBB-020726
Ambinter	Amb1150362	http://www.ambinter.com/reference/1150362
Angel Pharmatech	AG109244	http://www.angelpharmatech.com/90-45-9.html
Angene	AGN-PC-0JK7VC	http://www.angenechemical.com/productshow/AGN-PC-0JK7VC.html
Anward	ANW-75188	http://www.anward.com/pro_result/61639
Ark Pharm	AK109135	http://www.arkpharminc.com/products/90-45-9.html
Aurum Pharmatech LLC	M-2337	http://www.Aurumpharmatech.com/Product/ProductDetails/M_2337
Avantor Inc	200010-864	https://us.vwr.com/store/product/18599285/9-aminoacridine-hemihydrate
BLD Pharm	BD14518	http://www.bldpharm.com/products/90-45-9.html
BioChemPartner	BCP25849	http://www.biochempartner.com/90-45-9-BCP25849
CSNpharm	CSN11568	https://www.csnpharm.com/products/9-aminoacridine.html
Chem Scene	CS-4915	http://www.chemscene.com/90-45-9.html
ChemFish Tokyo co.,ltd	7019	http://www.chemfish.co.jp/index.php?id=2464&project=product
Chemenu	CM119179	http://www.chemenu.com/products/CM119179
Chemspace	CSSB00000183055	https://chem-space.com/CSSB00000183055
DC Chemicals	DC37402	http://www.dcchemicals.com//product_show-Aminoacridine.html
Debye Scientific	DB-026983	http://www.debyesci.com/DB-026983.html
Finetech	FT-0621612	http://www.finetechnology-ind.com/prod/detail/pub/90-45-9.html
Hairui	HR134673	http://www.hairuichem.com/en/product/90-45-9.html
Hefei Hirisun Pharmatech Co., Ltd	HR120307	http://www.hirisunpharm.com/90-45-9.html
Lab Network	LN00178594	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00178594
Matrix Scientific	79751	https://www.matrixscientific.com/079751.html
MedChem Express	HY-B1422	https://www.medchemexpress.com/9-Aminoacridine.html
Molcore	MC454464	https://www.molcore.com/product/90-45-9
MuseChem	R053827	https://www.musechem.com/product/R053827.html
Oakwood	235796	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=116795&ExtHyperLink=1
Otava	1311314	https://search.otavachemicals.com/#!/search?query=1311314&type=code&base=dbb
Sigma-Aldrich	92817_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/92817?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017810	http://www.sinfoobiotech.com/product/1021208
Smolecule	S518501	http://www.smolecule.com/products/s518501
Smolecule	S793384	https://www.smolecule.com/products/s793384
TCI (Tokyo Chemical Industry)	A2905	http://www.tcichemicals.com/eshop/en/us/commodity/A2905/index.html
THE BioTek	bt-259339	https://www.thebiotek.com/product/inhibitors/bt-259339
Vitas-M Laboratory	BBL011755	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL011755&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL260686-1G	https://www.vladachem.com/product.php?products=90-45-9
Yuhao Chemical	RT2025	http://www.chemyuhao.com/90-45-9.html
abcr GmbH	AB336861	http://www.abcr.com/shop/en/AB336861
mcule	MCULE-4734217474	https://mcule.com/MCULE-4734217474/

PubMed

Title	Date	PubMed
Acridin-9-yl exchange: a proposal for the action of some 9-aminoacridine drugs.	2006	16933221
Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity.	2007	18364995
Analysis of low molecular weight acids by negative mode matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.	2007	17880046
Quantitative detection of metabolites using matrix-assisted laser desorption/ionization mass spectrometry with 9-aminoacridine as the matrix.	2007	17546650
Imaging Matrix Assisted Laser Desorption Ionization Mass Spectrometry: a technique to map plant metabolites within tissues at high spatial resolution.	2007	17005924
Discriminating between cellular and misfolded prion protein by using affinity to 9-aminoacridine compounds.	2007 Apr	17374787
A real-time fluorescence assay for measuring N-dealkylation.	2007 Jan	17035601
Preparation of magnetite nanocrystals with surface reactive moieties by one-pot reaction.	2007 Jul 15	17433352
Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions.	2007 Jul 6	17552568
A binary matrix for background suppression in MALDI-MS of small molecules.	2007 Mar	17260136
Molecular recognition of DNA by rigid [N]-polynorbornane-derived bifunctional intercalators: synthesis and evaluation of their binding properties.	2007 May 17	17429957
The electrochemical behavior and direct determination of tyrosine at a glassy carbon electrode modified with poly (9-aminoacridine).	2007 Oct	18153995
A role of the 9-aminoacridines and their conjugates in a life science.	2007 Oct	17979762
Modulation of the genotoxicity of bleomycin by amines through noncovalent DNA interactions and alteration of physiological conditions in yeast.	2007 Oct 1	17428504
Ultrasonic trapping of microparticles in suspension and reaction monitoring using Raman microspectroscopy.	2007 Oct 15	17874849
Frameshift mutations produced by 9-aminoacridine in wild-type, uvrA and recA strains of Escherichia coli; specificity within a hotspot.	2007 Sep	17611351
In silico chemical library screening and experimental validation of a novel 9-aminoacridine based lead-inhibitor of human S-adenosylmethionine decarboxylase.	2007 Sep-Oct	17676832
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	18338375
Effect of spermine conjugation on the interaction of acridine with alternating purine-pyrimidine oligodeoxyribonucleotides studied by CD, fluorescence and absorption spectroscopies.	2008 Apr	17644401
New palladium(II) and platinum(II) complexes with 9-aminoacridine: structures, luminiscence, theoretical calculations, and antitumor activity.	2008 Aug 4	18593114
Drug 9AA reactivates p21/Waf1 and Inhibits HIV-1 progeny formation.	2008 Mar 18	18348731
Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage.	2008 May 15	18450456
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	18767869
Biological safety of liposome-fullerene consisting of hydrogenated lecithin, glycine soja sterols, and fullerene-C60 upon photocytotoxicity and bacterial reverse mutagenicity.	2009 Apr	19482914
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	19251414
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	19690837
Blockade of NMDA receptor channels by 9-aminoacridine and its derivatives.	2009 Feb 13	19111901
9-Aminoacridine-based anticancer drugs target the PI3K/AKT/mTOR, NF-kappaB and p53 pathways.	2009 Feb 26	19137016
Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II.	2009 Jan 14	19071108
Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.	2009 Jan 22	19113955
In situ primary metabolites localization on a rat brain section by chemical mass spectrometry imaging.	2009 Jul 1	19514699
9-Aminoacridine inhibition of HIV-1 Tat dependent transcription.	2009 Jul 24	19630958
Biological safety of LipoFullerene composed of squalane and fullerene-C60 upon mutagenesis, photocytotoxicity, and permeability into the human skin tissue.	2009 Jun	19371265
Identification of chemical compounds that induce HIF-1alpha activity.	2009 Nov	19502547
Binding of TCA to the prion protein: mechanism, implication for therapy, and application as probe for complex formation of bio-macromolecules.	2009 Oct	19583442
A kinetic and structural investigation of DNA-based asymmetric catalysis using first-generation ligands.	2009 Sep 21	19579236
Investigation on the Interactions of NiCR and NiCR-2H with DNA.	2010	20671951
Alveolar osteitis: a comprehensive review of concepts and controversies.	2010	20652078
Host hindrance to HIV-1 replication in monocytes and macrophages.	2010 Apr 7	20374633
The intact muscle lipid composition of bulls: an investigation by MALDI-TOF MS and 31P NMR.	2010 Feb	19900429
Genotoxicity and antigenotoxicity evaluation of non-photoactivated hypericin.	2010 Jan	19585477
Lipidomic analysis of porcine olfactory epithelial membranes and cilia.	2010 Jul	20512424
Mutagenic and antimutagenic effects of hexane extract of some Astragalus species grown in the eastern Anatolia region of Turkey.	2010 Jul	19957249
Significant sensitivity improvements by matrix optimization: a MALDI-TOF mass spectrometric study of lipids from hen egg yolk.	2010 Jun	20420816
Selective desorption/ionization of sulfatides by MALDI-MS facilitated using 9-aminoacridine as matrix.	2010 Jun	20124011
Modulation of mdm2 pre-mRNA splicing by 9-aminoacridine-PNA (peptide nucleic acid) conjugates targeting intron-exon junctions.	2010 Jun 30	20591158
The surface charge density of plant cell membranes (sigma): an attempt to resolve conflicting values for intrinsic sigma.	2010 May	20435694
Molecular docking studies of selected tricyclic and quinone derivatives on trypanothione reductase of Leishmania infantum.	2010 Oct	20340105
MALDI-TOF/MS analysis of archaebacterial lipids in lyophilized membranes dry-mixed with 9-aminoacridine.	2010 Sep	20538644
Mononuclear Fe(II)-N4Py complexes in oxidative DNA cleavage: structure, activity and mechanism.	2010 Sep 14	20657939

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.

Name

Type

Language

AMINACRINE

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

Official Name

English

Classification Tree Code System Code

WHO-ATC

D08AA02