PROFLAVINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H11N3
Molecular Weight	209.2465
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC2=NC3=CC(N)=CC=C3C=C2C=C1

InChI

InChIKey=WDVSHHCDHLJJJR-UHFFFAOYSA-N

InChI=1S/C13H11N3/c14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10/h1-7H,14-15H2

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB01123
Curator's Comment: description was created based on several sources, including https://www.drugs.com/uk/proflavine-cream-0-1-leaflet.html | https://www.ncbi.nlm.nih.gov/pubmed/22594981 | https://clinicaltrials.gov/ct2/show/NCT02029937

Proflavine is an acriflavine derivative used as a topical disinfectant agains gram-positive bacteria. Proflavine is toxic and carcinogenic in mammals and so it is used only as a surface disinfectant or for treating superficial wounds. Proflavine acts by interchelating DNA (intercalation), thereby disrupting DNA synthesis and leading to high levels of mutation in the copied DNA strands. This prevents bacterial reproduction. Proflavine was investigated for photodynamic theraphy of herpes but was discontinued due to several presentations of post-treatment Bowen's disease and higher lesion recrudescence periods. Proflavine is also investigated as a topical contrast agent for imaging and diagnosis of esophageal, oral, colon, cervical, uterine cancer and polyps.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL3140325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19364280	Binding Agent 1076
RNA 19 Target ID: CHEMBL2311222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5341263	Binding Agent 1076

Conditions

Condition	Modality	Highest Phase	Product
Gram-positive bacterial infections 8 Sources: https://www.drugs.com/uk/proflavine-cream-0-1-leaflet.html	Preventing	Approved 8583	PROFLAVINE CREAM 0.1% Approved Use For treatment of infected wounds and for skin disinfection
Genital herpes 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/216264	Primary	Phase II 1147	Unknown Approved Use Unknown
Barrett’s esophagus 7 Sources: https://clinicaltrials.gov/ct2/show/NCT02029937	Diagnostic	Phase II 1147	Unknown Approved Use Unknown
Head and neck cancer 50 Sources: https://clinicaltrials.gov/ct2/show/NCT01269190	Diagnostic	Not Provided 511	Unknown Approved Use Unknown
Cervical cancer 40 Sources: https://clinicaltrials.gov/ct2/show/NCT02206048	Diagnostic	Phase I 438	Unknown Approved Use Unknown
Colon polyps 5 Sources: https://clinicaltrials.gov/ct2/show/NCT01384240	Diagnostic	Phase I 438	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY533450	https://www.001chemical.com/chem/1811-28-5
001 Chemical	DY580060	https://www.001chemical.com/chem/92-62-6
3B Scientific (Wuhan) Corp	3B2-4353	http://www.3bsc.com/index/pro_info.php?id=79293
abcr GmbH	AB549695	http://www.abcr.com/shop/en/AB549695
Alfa Chemistry	ACM92626-1	https://mof.alfa-chemistry.com/product/3-6-acridinediamine-cas-92-62-6-295483.html
Alichem	449041438	http://www.alichem.com/en/products/92-62-6.html
Alinda	ALBB-024962	http://alinda.ru/finechem_en_.html?i=ALBB-024962
Angene	AGN-PC-0JK7WW	http://www.angenechemical.com/productshow/AGN-PC-0JK7WW.html
Aurum Pharmatech LLC	R1243	http://www.Aurumpharmatech.com/Product/ProductDetails/R1243
BLD Pharm	BD599094	http://www.bldpharm.com/products/92-62-6.html
Chem Scene	CS-0013756	http://www.chemscene.com/92-62-6.html
ChemMol	49417044	http://www.chemmol.com/chemmol/49417044.html
ChemMol	49430334	http://www.chemmol.com/chemmol/49430334.html
Chemspace	CSSB00020600607	https://chem-space.com/CSSB00020600607
DC Chemicals	DC20192	http://www.dcchemicals.com/product_show-DC20192.html
Glentham Life Sciences	GT1397	http://www.glentham.com/products/product/GT1397/
Lab Network	LN00237938	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00237938
Matrix Scientific	156639	https://www.matrixscientific.com/156639.html
mcule	MCULE-9362278105	https://mcule.com/MCULE-9362278105/
Molcore	MC533450	https://www.molcore.com/product/1811-28-5
Molcore	MC580060	https://www.molcore.com/product/92-62-6
Oakwood	374648	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=146126&ExtHyperLink=1
Sigma-Aldrich	PH006894_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/ph006894
Smolecule	S540242	http://www.smolecule.com/products/s540242
THE BioTek	bt-280003	https://www.thebiotek.com/product/inhibitors/bt-280003
Vitas-M Laboratory	BBL002984	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL002984&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink

PubMed

Title	Date	PubMed
Magnetic field effect corroborated with docking study to explore photoinduced electron transfer in drug-protein interaction.	2010-12-30	21126029
Synthesis, characterization and cytotoxicity studies of palladium(II)-proflavine complexes.	2010-11	20709409
Interaction of bioactive coomassie brilliant blue g with protein: insights from spectroscopic methods.	2010-08-26	21179322
Change of the binding mode of the DNA/proflavine system induced by ethanol.	2010-07-01	20524626
A fiber-optic fluorescence microscope using a consumer-grade digital camera for in vivo cellular imaging.	2010-06-23	20585636
The nature of the force-induced conformation transition of dsDNA studied by using single molecule force spectroscopy.	2010-06-15	20178341
"Weighing" photon energies with mass spectrometry: effects of water on ion fluorescence.	2010-05-26	20438075
Toxicology and drug delivery by cucurbit[n]uril type molecular containers.	2010-05-06	20463906
Design and evaluation of an ultra-slim objective for in-vivo deep optical biopsy.	2010-03-01	20389489
[Experimental study of proflavine acetate phototransformation processes].	2010-01-06	20050062
Triple dye plus rubbing alcohol versus triple dye alone for umbilical cord care.	2010-01	20034947
[Features of binding of proflavine to DNA at different DNA-ligand concentration ratios].	2009-11-10	19894617
Equine rhinitis A virus and its low pH empty particle: clues towards an aphthovirus entry mechanism?	2009-10	19816570
[Catalytical properties of the liver monoamine oxidases of the commander squid Berryteuthis magister from various habitation zones].	2009-09-22	19764634
Stacking interactions and DNA intercalation.	2009-08-13	19719266
Abstracts of the 2008 ISSOL Meeting. August 24-29, 2008. Florence, Italy.	2009-08	19468860
1H and 13C NMR signal assignments of some new N,N'-diacyl proflavine derivatives.	2009-08	19459182
Isothermal microcalorimetry to investigate non specific interactions in biophysical chemistry.	2009-07-28	20111693
Precambrian lunar volcanic protolife.	2009-06-11	19582224
Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine.	2009-06	19217190
Complexation of biologically active aromatic compounds with DNA in the presence of theophylline.	2009-05	19669556
Solution structure and thermodynamics of 2',5' RNA intercalation.	2009-04-29	19309071
Interaction of small molecules with double-stranded RNA: spectroscopic, viscometric, and calorimetric study of hoechst and proflavine binding to PolyCG structures.	2009-04	19364280
Fluorophore labeling to monitor tRNA dynamics.	2009	20946785
Skipjack tuna (Katsuwonus pelamis) liver monoamine oxidase: substrate-inhibitor analysis.	2008-10-16	18853783
Pyrrolo-C as a molecular probe for monitoring conformations of the tRNA 3' end.	2008-10	18755841
Electroanalytical study of proflavine intercalation in 5-methyl or inosine-containing amplicons.	2008-10	18677465
QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization.	2008-08-05	18616285
Conformational dynamics at the active site of alpha-chymotrypsin and enzymatic activity.	2008-08-05	18572890
Colicin E3 cleavage of 16S rRNA impairs decoding and accelerates tRNA translocation on Escherichia coli ribosomes.	2008-07	18485067
Role of the third strand in the binding of proflavine and pt-proflavine to poly(rA).2poly(rU): a thermodynamic and kinetic study.	2008-06-12	18491933
Self-structure induction in single stranded poly(A) by small molecules: Studies on DNA intercalators, partial intercalators and groove binding molecules.	2008-06-01	18387354
Complexation and fluorescence of tricyclic basic dyes encapsulated in cucurbiturils.	2008-04-04	18330855
Cytotoxic activity of proflavine diureas: synthesis, antitumor, evaluation and DNA binding properties of 1',1''-(acridin-3,6-diyl)-3',3''-dialkyldiureas.	2008-04-01	18258438
Label free electrochemical DNA hybridization discrimination effects at the binary and ternary mixed monolayers of single stranded DNA/diluent/s in presence of cationic intercalators.	2008-03-14	18187315
Over-expression of genes coding for proline oxidase, riboflavin kinase, cytochrome c oxidase and an MFS transporter induced by acriflavin in Trichophyton rubrum.	2008-03	18324492
Spectroscopic studies on ligand-enzyme interactions: complexation of alpha-chymotrypsin with 4',6-diamidino-2-phenylindole (DAPI).	2008-02-14	18205349
A randomised controlled trial of a double layer of Allevyn compared to Jellonet and proflavin as a tie-over dressing for small skin grafts.	2008	18436169
DNA binding by a new metallointercalator that contains a proflavine group bearing a hanging chelating unit.	2008	17853515
[Comparative toxicity of photosensitizers in varying destruction].	2007-12-07	18050705
Protonation linked equilibria and apparent affinity constants: the thermodynamic profile of the alpha-chymotrypsin-proflavin interaction.	2007-12	17443320
Catalytic properties of monoamine oxidase from mink (Mustela vison) liver.	2007-10-16	17933335
Ligand-transporter interaction in the AcrB multidrug efflux pump determined by fluorescence polarization assay.	2007-10-16	17910961
Quantifying RNA-peptide interaction by single-quantum dot-based nanosensor: an approach for drug screening.	2007-10-15	17877365
Characterization of the multidrug efflux regulator AcrR from Escherichia coli.	2007-09-14	17644067
Fluorescent labeling of tRNAs for dynamics experiments.	2007-09	17652134
On the origin of the decrease in stability of the DNA hairpin d(GCGAAGC) on complexation with aromatic drugs.	2007-08	17544564
A rare cause of breast mass that mimics carcinoma: Foreign body reaction to amorphous surgical material.	2007	17721770
Progressing single biomolecule force spectroscopy measurements for the screening of DNA binding agents.	2005-10	20818013
Amino acridines action on Friend's retrovirus in relation to their molecular ionization.	1989	2790144

Patents

Sample Use Guides

In Vivo Use Guide

Proflavine cream 0.1% is indicated for topical use, to be applied to the affected part 2 - 3 times daily.

Route of Administration: Topical

In Vitro Use Guide

The minimal inhibition concentration (MIC) of proflavine with respect to various E.coli strains was determined by the twofold dilution method with LB agar containing the proflavine. Bacterial growth was recorded after 18 to 24 h of incubation at 37°C. Proflavine was effective in supressing bacterial growth at 6.5-12.5 ug/mL.

Name

Type

Language

PROFLAVINE

Official Name

English

PROFLAVINE [HSDB]

Preferred Name

English

proflavine [INN]

Common Name

English

Proflavine [WHO-DD]

Common Name

English

PROFLAVINE [VANDF]

Common Name

English

3,6-DIAMINOACRIDINE

Systematic Name

English

PROFLAVINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28394