Banner
targets (1) transporters (1)
for drugs
Identification
Name Gentian Violet
Accession Number DB00406 (APRD00998)
Type small molecule
Groups approved
Description

A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties. [PubChem]

Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Crystal Violet
Brand names
  • Adergon
  • Aizen Crystal Violet
  • Aizen Crystal Violet Extra Pure
  • Aniline Violet
  • Aniline Violet pyoktanine
  • Atmonil
  • Avermin
  • Axuris
  • Badil
  • Basic Violet 3
  • Basic Violet BN
  • Basic Violet-3
  • Bismuth Violet
  • Brilliant Violet 5B
  • C.I. Basic Violet 3
  • Calcozine Violet 6BN
  • Calcozine Violet C
  • Crystal Violet 10B
  • Crystal Violet 5BO
  • Crystal Violet 6B
  • Crystal Violet 6BO
  • Crystal Violet AO
  • Crystal Violet AON
  • Crystal Violet base
  • Crystal Violet BP
  • Crystal Violet BPC
  • Crystal Violet chloride
  • Crystal Violet chloride salt
  • Crystal Violet Extra Pure
  • Crystal Violet Extra Pure APN
  • Crystal Violet Extra Pure APNX
  • Crystal Violet FN
  • crystal violet for microscopy
  • Crystal Violet HL2
  • Crystal Violet O
  • Crystal Violet Pure DSC
  • Crystal Violet Pure DSC Brilliant
  • Crystal Violet SS
  • Crystal Violet Technical
  • Crystal Violet USP
  • Genapax
  • Gentersal
  • gentian violet gr
  • Gentiaverm
  • Genticid
  • Gentioletten
  • gention violet alchoholic staining solution
  • GV-Eleven
  • Gvs
  • Hecto Violet R
  • Hectograph Violet SR
  • Hexamethyl Violet
  • Hexamethylpararosaniline chloride
  • Hidaco Brilliant Crystal Violet
  • Hidaco crystal Violet
  • Meroxyl-Wander
  • Meroxylan-Wander
  • Methyl violet
  • Methyl Violet 10B
  • Methyl Violet 10BD
  • Methyl Violet 10BK
  • Methyl Violet 10BN
  • Methyl Violet 10BNS
  • Methyl Violet 10BO
  • Methyl Violet 5BNO
  • Methyl Violet 5BO
  • Methyl Violet 6B
  • Methylrosaniline chloride
  • methylrosanilinium chloride
  • Mitsui Crystal Violet
  • Oxiuran
  • Oxycolor
  • Oxyozyl
  • Paper Blue R
  • Plastoresin Violet 5BO
  • Pyoktanin
  • Vermicid
  • Vianin
  • Viocid
  • Violet 5BO
  • Violet 6BN
  • Violet CP
  • Violet XXIII
Brand name mixtures
  • Blu Kote Dr Naylors (Acriflavine + Gentian Violet + Glycerine + Isopropyl Alcohol + Sodium Propionate + Urea)
  • Blue Lotion (Gentian Violet + Methylene Blue + Tannic Acid)
  • Co-Op Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate))
  • Cristisol (Acriflavine + Gentian Violet + Isopropyl Alcohol)
  • Pink Eye Guard (Allantoin + Boric Acid + Gentian Violet)
  • Pink Eye Spray (Furfural + Gentian Violet + Isopropyl Alcohol + Methylene Blue + Phenylmercuric Nitrate (Basic) + Tetrahydrofurfuryl Alcohol + Urea)
  • Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate))
  • Triple Dye (Brilliant Green + Gentian Violet + Proflavine Hemisulfate)
  • Wound & Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate))
  • Wound Kote Gentian Violet Spray Wound Dre (Acriflavine + Furfural + Methyl Violet + Sodium Propionate + Urea)
Categories
  • Anti-Infective Agents, Local
CAS number 14426-25-6
Weight Average: 372.5258
Monoisotopic: 372.243972975
Chemical Formula C25H30N3
InChI Key InChIKey=LGLFFNDHMLKUMI-UHFFFAOYSA-N
InChI
InChI=1S/C25H30N3/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6/h7-18H,1-6H3/q+1
Plain Text
IUPAC Name
4-{bis[4-(dimethylamino)phenyl]methylidene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium
SMILES
CN(C)C1=CC=C(C=C1)C(C1=CC=C(C=C1)N(C)C)=C1C=CC(C=C1)=[N+](C)C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylpropenes
  • Styrene Derivatives
Substructures
  • Alkanes and Alkenes
  • Aliphatic and Aryl Amines
  • Phenylpropenes
  • Benzene and Derivatives
  • Isoprenes
  • Aromatic compounds
  • Imines
  • Styrene Derivatives
  • Anilines
  • Cations
Pharmacology
Indication For the treatment of bacterial and fungal infections inside the mouth (thrush) and skin, also for the prevention of transmission of Chagas' disease (as a blood additive).
Pharmacodynamics Gentian violet is a mutagen, a mitotic poison, and a clastogen. Gentian violet has been used in medicine for almost 100 years: as an antiseptic for external use, as a topical antibiotic, as a topical antifungal agent, as an antihelminthic agent by oral administration, and more recently, as a blood additive to prevent transmission of Chagas' disease. It is thought to work by binding to the DNA of target organisms and causing disruption, mutation or inhibition of DNA replication.
Mechanism of action In aqueous solutions Gentian violet (GV) dissociates into positive (GV+)and negative ions (Cl-) that penetrate through the wall and membrane of both gram-positive and gram-negative bacterial cells. The GV+ interacts with negatively charged components of bacterial cells including the lipopolysaccharide (on the cell wall), the peptidoglycan and DNA. A similar cell penetration and DNA binding process is thought to take place for fungal cells as well. Because Gentian violet is a mutagen and mitotic poison, cell growth is consequently inhibited. A photodynamic action of gentian violet, apparently mediated by a free-radical mechanism, has recently been described in bacteria and in the protozoan T. cruzi. Evidence also suggests that gentian violet dissipates the bacterial (and mitochondrial) membrane potential by inducing permeability. This is followed by respiratory inhibition. This anti-mitochondrial activity might explain gentian violet's efficacy towards both bacteria and yeast with relatively mild effects on mammalian cells.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Primarily hepatic, mostly demethylation

Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity LD50=420 mg/kg (rat, oral). Oral administration can cause gastrointestinal irritation, and intravenous injection can cause depression in the white blood cell count.
Affected organisms
  • Yeast and other fungi
  • Bacteria and protozoa
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Savage laboratories inc div altana inc
  • Key pharmaceuticals inc sub schering plough corp
Packagers
Dosage forms
Form Route Strength
Liquid Topical
Prices
Unit description Cost Unit
Gentian violet 2% solution 0.16 USD ml
Gentian violet 1% solution 0.08 USD ml
Patents Not Available
Properties
State solid
Melting point 215 oC
Experimental Properties
Property Value Source
water solubility 4 mg/mL PhysProp
logP 3.18 PhysProp
Predicted Properties
Property Value Source
water solubility 1.93e-03 g/l ALOGPS
logP 0.87 ALOGPS
logP 1.40 ChemAxon Molconvert
logS -5.32 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 9.49 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 146.00 ChemAxon Molconvert
polarizability 45.60 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01046 Link_out
PubChem Compound 3468 Link_out
PubChem Substance 46505353 Link_out
ChemSpider 3349 Link_out
PharmGKB PA449755 Link_out
Drug Product Database 50857 Link_out
Drugs.com http://www.drugs.com/cons/gentian-violet-topical.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Gentian_Violet Link_out
ATC Codes
  • D01AE02
AHFS Codes
  • 84:04.08.92
PDB Entries Not Available
FDA label Not Available
MSDS show (77.1 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. DNA

Pharmacological action: yes
Actions: intercalation

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Gene Sequence: FASTA

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Docampo R, Moreno SN: The metabolism and mode of action of gentian violet. Drug Metab Rev. 1990;22(2-3):161-78. Pubmed
  4. Si WH, Zi YQ: [Studies on the interaction between RNA with methyl violet and determination of RNA by spectrophotometry]. Guang Pu Xue Yu Guang Pu Fen Xi. 2005 Nov;25(11):1846-9. Pubmed

Transporters

1. Solute carrier family 22 member 1

Actions: inhibitor

Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase

UniProt ID: O15245 Link_out
Gene: SLC22A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on January 27, 2011 09:17

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.