DrugBank: Gentian Violet (DB00406)

targets (1) transporters (1)

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

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

Humco

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
PubChem Compound	3468
PubChem Substance	46505353
ChemSpider	3349
PharmGKB	PA449755
Drug Product Database	50857
Drugs.com	http://www.drugs.com/cons/gentian-violet-topical.html
Wikipedia	http://en.wikipedia.org/wiki/Gentian_Violet

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: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 Docampo R, Moreno SN: The metabolism and mode of action of gentian violet. Drug Metab Rev. 1990;22(2-3):161-78. Pubmed 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

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:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
Docampo R, Moreno SN: The metabolism and mode of action of gentian violet. Drug Metab Rev. 1990;22(2-3):161-78. Pubmed
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 Gene: SLC22A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

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:

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.