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
SMILES
NC1=CC2=NC3=C(C=CC(N)=C3)C=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
DescriptionCurator'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
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 |
|---|---|---|---|
Target ID: CHEMBL3140325 |
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Target ID: CHEMBL2311222 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | PROFLAVINE CREAM 0.1% Approved UseFor treatment of infected wounds and for skin disinfection |
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| Primary | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Amino acridines action on Friend's retrovirus in relation to their molecular ionization. | 1989 |
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| Progressing single biomolecule force spectroscopy measurements for the screening of DNA binding agents. | 2005 Oct |
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| Catalytic properties of monoamine oxidase from the lamprey Lampetrafluviatilis liver. | 2006 Sep-Oct |
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| A rare cause of breast mass that mimics carcinoma: Foreign body reaction to amorphous surgical material. | 2007 |
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| On the origin of the decrease in stability of the DNA hairpin d(GCGAAGC) on complexation with aromatic drugs. | 2007 Aug |
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| Protonation linked equilibria and apparent affinity constants: the thermodynamic profile of the alpha-chymotrypsin-proflavin interaction. | 2007 Dec |
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| Kinetically competent intermediates in the translocation step of protein synthesis. | 2007 Feb 23 |
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| Catalytic properties of monoamine oxidase from mink (Mustela vison) liver. | 2007 Jul-Aug |
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| Effects of guanosine on the pharmacokinetics of acriflavine in rats following the administration of a 1:1 mixture of acriflavine and guanosine, a potential antitumor agent. | 2007 Mar |
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| Synthesis and antileishmanial activity of 6-mono-substituted and 3,6-di-substituted acridines obtained by acylation of proflavine. | 2007 Oct |
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| Quantifying RNA-peptide interaction by single-quantum dot-based nanosensor: an approach for drug screening. | 2007 Oct 15 |
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| Ligand-transporter interaction in the AcrB multidrug efflux pump determined by fluorescence polarization assay. | 2007 Oct 16 |
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| Fluorescent labeling of tRNAs for dynamics experiments. | 2007 Sep |
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| Characterization of the multidrug efflux regulator AcrR from Escherichia coli. | 2007 Sep 14 |
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| [Comparative toxicity of photosensitizers in varying destruction]. | 2007 Sep-Oct |
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| 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 |
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| DNA binding by a new metallointercalator that contains a proflavine group bearing a hanging chelating unit. | 2008 |
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| Cytotoxic activity of proflavine diureas: synthesis, antitumor, evaluation and DNA binding properties of 1',1''-(acridin-3,6-diyl)-3',3''-dialkyldiureas. | 2008 Apr 1 |
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| Complexation and fluorescence of tricyclic basic dyes encapsulated in cucurbiturils. | 2008 Apr 4 |
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| QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization. | 2008 Aug 5 |
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| Spectroscopic studies on ligand-enzyme interactions: complexation of alpha-chymotrypsin with 4',6-diamidino-2-phenylindole (DAPI). | 2008 Feb 14 |
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| Colicin E3 cleavage of 16S rRNA impairs decoding and accelerates tRNA translocation on Escherichia coli ribosomes. | 2008 Jul |
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| Self-structure induction in single stranded poly(A) by small molecules: Studies on DNA intercalators, partial intercalators and groove binding molecules. | 2008 Jun 1 |
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| Role of the third strand in the binding of proflavine and pt-proflavine to poly(rA).2poly(rU): a thermodynamic and kinetic study. | 2008 Jun 12 |
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| Over-expression of genes coding for proline oxidase, riboflavin kinase, cytochrome c oxidase and an MFS transporter induced by acriflavin in Trichophyton rubrum. | 2008 Mar |
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| 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 Mar 14 |
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| Pyrrolo-C as a molecular probe for monitoring conformations of the tRNA 3' end. | 2008 Oct |
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| Fluorophore labeling to monitor tRNA dynamics. | 2009 |
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| Interaction of small molecules with double-stranded RNA: spectroscopic, viscometric, and calorimetric study of hoechst and proflavine binding to PolyCG structures. | 2009 Apr |
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| Solution structure and thermodynamics of 2',5' RNA intercalation. | 2009 Apr 29 |
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| Abstracts of the 2008 ISSOL Meeting. August 24-29, 2008. Florence, Italy. | 2009 Aug |
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| Stacking interactions and DNA intercalation. | 2009 Aug 13 |
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| Isothermal microcalorimetry to investigate non specific interactions in biophysical chemistry. | 2009 Jul 28 |
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| [Catalytical properties of the liver monoamine oxidases of the commander squid Berryteuthis magister from various habitation zones]. | 2009 Jul-Aug |
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| Photo-inducible cytotoxic and clastogenic activities of 3,6-di-substituted acridines obtained by acylation of proflavine. | 2009 Jun |
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| Precambrian lunar volcanic protolife. | 2009 Jun 11 |
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| Complexation of biologically active aromatic compounds with DNA in the presence of theophylline. | 2009 May |
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| Equine rhinitis A virus and its low pH empty particle: clues towards an aphthovirus entry mechanism? | 2009 Oct |
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| [Experimental study of proflavine acetate phototransformation processes]. | 2009 Sep-Oct |
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| [Features of binding of proflavine to DNA at different DNA-ligand concentration ratios]. | 2009 Sep-Oct |
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| Magnetic field effect corroborated with docking study to explore photoinduced electron transfer in drug-protein interaction. | 2010 Dec 30 |
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| Triple dye plus rubbing alcohol versus triple dye alone for umbilical cord care. | 2010 Jan |
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| Change of the binding mode of the DNA/proflavine system induced by ethanol. | 2010 Jul 1 |
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| The nature of the force-induced conformation transition of dsDNA studied by using single molecule force spectroscopy. | 2010 Jun 15 |
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| A fiber-optic fluorescence microscope using a consumer-grade digital camera for in vivo cellular imaging. | 2010 Jun 23 |
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| Design and evaluation of an ultra-slim objective for in-vivo deep optical biopsy. | 2010 Mar 1 |
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| "Weighing" photon energies with mass spectrometry: effects of water on ion fluorescence. | 2010 May 26 |
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| Toxicology and drug delivery by cucurbit[n]uril type molecular containers. | 2010 May 6 |
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| Synthesis, characterization and cytotoxicity studies of palladium(II)-proflavine complexes. | 2010 Nov |
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| Interaction of bioactive coomassie brilliant blue g with protein: insights from spectroscopic methods. | 2010 Oct-Dec |
Patents
Sample Use Guides
Proflavine cream 0.1% is indicated for topical use, to be applied to the affected part 2 - 3 times daily.
Route of Administration:
Topical
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.
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C28394
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SUB10073MIG
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92-62-6
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C77055
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CHEMBL55400
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PROFLAVINE
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7071
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8723
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8452
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2277
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
