PROFLAVINE DIHYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H11N3.2ClH
Molecular Weight	282.168
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.NC1=CC2=NC3=C(C=CC(N)=C3)C=C2C=C1

InChI

InChIKey=YHIHFKAEJAVELI-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C13H11N3
Molecular Weight	209.2465
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

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 278 Target ID: CHEMBL3140325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19364280	Binding Agent 1064
RNA 19 Target ID: CHEMBL2311222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5341263	Binding Agent 1064

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 8429	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 1132	Unknown Approved Use Unknown
Barrett’s esophagus 7 Sources: https://clinicaltrials.gov/ct2/show/NCT02029937	Diagnostic	Phase II 1132	Unknown Approved Use Unknown
Head and neck cancer 50 Sources: https://clinicaltrials.gov/ct2/show/NCT01269190	Diagnostic	Not Provided 504	Unknown Approved Use Unknown
Cervical cancer 40 Sources: https://clinicaltrials.gov/ct2/show/NCT02206048	Diagnostic	Phase I 428	Unknown Approved Use Unknown
Colon polyps 5 Sources: https://clinicaltrials.gov/ct2/show/NCT01384240	Diagnostic	Phase I 428	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
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
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
abcr GmbH	AB549695	http://www.abcr.com/shop/en/AB549695
mcule	MCULE-9362278105	https://mcule.com/MCULE-9362278105/

PubMed

Title	Date	PubMed
Proflavine-mediated inactivation of Salmonella dublin exposed to visible sunlight in natural fresh water.	2001	11393749
Contact dermatitis complicating pinnaplasty.	2001 Apr	11254419
Hydration changes for DNA intercalation reactions.	2001 Jan 10	11273594
Dialysis cells for controlled DNA: drug binding studies.	2001 Jun	11445950
Gene recognition in eukaryotic DNA by comparison of genomic sequences.	2001 Nov	11724729
Inhibition of human neutrophil elastase by erythromycin and flurythromycin, two macrolide antibiotics.	2001 Oct	11694455
Hetero-association of caffeine and aromatic drugs and their competitive binding with a DNA oligomer.	2001 Sep	11592692
Effects of anticancer drugs on transcription in vitro.	2001 Sep-Oct	11724400
Randomized trial of alcohol versus triple dye for umbilical cord care.	2002 Jul-Aug	12166794
[NMR study of complex formation of aromatic ligands with heptadeoxynucleotide 5'-d(GCGAAGC) forming stable hairpin structure in aqueous solution].	2002 Sep-Oct	12391853
Changes in newborn bathing practices may increase the risk for omphalitis.	2004 Oct	15494885
A fluorescence stopped-flow kinetic study of the conformational activation of alpha-chymotrypsin and several mutants.	2004 Sep	15322291
Pharmacokinetics and metabolism of acriflavine in rats following intravenous or intramuscular administration of AG60, a mixture of acriflavine and guanosine, a potential antitumour agent.	2005 Jul	16323364
A randomized study of 3 umbilical cord care regimens at home in thai neonates: comparison of time to umbilical cord separation, parental satisfaction and bacterial colonization.	2005 Jul	16241027
Time-resolved EPR spectra of the triplet excited states of diaminoacridine guests in polar potassium hydrogen phthalate single crystals.	2006 Jan 21	16482281
Physical nature of ethidium and proflavine interactions with nucleic acid bases in the intercalation plane.	2006 May 18	16686524
Catalytic properties of monoamine oxidase from the lamprey Lampetrafluviatilis liver.	2006 Sep-Oct	17286100
Catalytic properties of monoamine oxidase from mink (Mustela vison) liver.	2007 Jul-Aug	17933335
Characterization of the multidrug efflux regulator AcrR from Escherichia coli.	2007 Sep 14	17644067
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	18258438
QacR-cation recognition is mediated by a redundancy of residues capable of charge neutralization.	2008 Aug 5	18616285
Spectroscopic studies on ligand-enzyme interactions: complexation of alpha-chymotrypsin with 4',6-diamidino-2-phenylindole (DAPI).	2008 Feb 14	18205349
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	18324492
Pyrrolo-C as a molecular probe for monitoring conformations of the tRNA 3' end.	2008 Oct	18755841
Isothermal microcalorimetry to investigate non specific interactions in biophysical chemistry.	2009 Jul 28	20111693
Magnetic field effect corroborated with docking study to explore photoinduced electron transfer in drug-protein interaction.	2010 Dec 30	21126029
Change of the binding mode of the DNA/proflavine system induced by ethanol.	2010 Jul 1	20524626
"Weighing" photon energies with mass spectrometry: effects of water on ion fluorescence.	2010 May 26	20438075
Synthesis, characterization and cytotoxicity studies of palladium(II)-proflavine complexes.	2010 Nov	20709409

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:45:12 GMT 2023` Edited by `admin` on `Fri Dec 15 15:45:12 GMT 2023`
Record UNII	86EZ5R5IR1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROFLAVINE DIHYDROCHLORIDE

Common Name

English

PROFLAVINE DIHYDROCHLORIDE [MI]

Common Name

English

3,6-DIAMINOACRIDINIUM CHLORIDE HYDROCHLORIDE

Systematic Name

English

3,6-DIAMINOACRIDINE DIHYDROCHLORIDE

Systematic Name

English

PROFLAVINE HYDROCHLORIDE

Common Name

English

Proflavine dihydrochloride [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28394