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targets (1) transporters (1)
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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
Salts Not Available
Brand names
Name Company
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 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
First Prev Next Last
Brand mixtures
Brand Name Ingredients
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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 215 °C Not Available
water solubility 4 mg/mL Not Available
logP 3.18 Not Available
Predicted Properties
Property Value Source
water solubility 1.93e-03 g/l ALOGPS
logP 0.87 ALOGPS
logP 1.4 ChemAxon
logS -5.3 ALOGPS
pKa (strongest basic) 4.83 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 9.49 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 146 ChemAxon
polarizability 45.6 ChemAxon
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 Not Available
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 February 08, 2013 16:19