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Identification
NameGentian Violet
Accession NumberDB00406  (APRD00998)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
Crystal VioletNot AvailableNot Available
Crystal violet carbocationNot AvailableNot Available
Crystal violet ion(1)Not AvailableNot Available
Crystal violet(1+)Not AvailableNot Available
Gentian violet carbocationNot AvailableNot Available
Gentian violet cationNot AvailableNot Available
Gentian violet(1+)Not AvailableNot Available
Methyl Violet 10BNot AvailableNot Available
PyoctaninNot AvailableNot Available
PyoctanineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Gentian Violet Chloride
Thumb
  • InChI Key: ZXJXZNDDNMQXFV-UHFFFAOYSA-M
  • Monoisotopic Mass: 407.212825682
  • Average Mass: 407.979
DBSALT000604
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number14426-25-6
WeightAverage: 372.5258
Monoisotopic: 372.243972975
Chemical FormulaC25H30N3
InChI KeyLGLFFNDHMLKUMI-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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassDiphenylmethanes
Direct parentDiphenylmethanes
Alternative parentsPhenylpropenes; Azomethines; Tertiary Amines; Polyamines
Substituentsphenylpropene; azomethine; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Pharmacology
IndicationFor 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).
PharmacodynamicsGentian 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 actionIn 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily hepatic, mostly demethylation

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.5643
Blood Brain Barrier + 0.7198
Caco-2 permeable + 0.6321
P-glycoprotein substrate Non-substrate 0.5936
P-glycoprotein inhibitor I Non-inhibitor 0.6474
P-glycoprotein inhibitor II Non-inhibitor 0.5747
Renal organic cation transporter Non-inhibitor 0.5959
CYP450 2C9 substrate Non-substrate 0.7272
CYP450 2D6 substrate Non-substrate 0.7573
CYP450 3A4 substrate Substrate 0.5753
CYP450 1A2 substrate Inhibitor 0.5787
CYP450 2C9 substrate Non-inhibitor 0.8225
CYP450 2D6 substrate Non-inhibitor 0.5732
CYP450 2C19 substrate Non-inhibitor 0.8028
CYP450 3A4 substrate Non-inhibitor 0.667
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7973
Ames test Non AMES toxic 0.9132
Carcinogenicity Carcinogens 0.8444
Biodegradation Not ready biodegradable 0.9944
Rat acute toxicity 2.5102 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9172
hERG inhibition (predictor II) Non-inhibitor 0.7075
Pharmacoeconomics
Manufacturers
  • Savage laboratories inc div altana inc
  • Key pharmaceuticals inc sub schering plough corp
Packagers
Dosage forms
FormRouteStrength
LiquidTopical
Prices
Unit descriptionCostUnit
Gentian violet 2% solution0.16USDml
Gentian violet 1% solution0.08USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point215 °CNot Available
water solubility4 mg/mLNot Available
logP3.18Not Available
Predicted Properties
PropertyValueSource
water solubility1.93e-03 g/lALOGPS
logP0.87ALOGPS
logP1.4ChemAxon
logS-5.3ALOGPS
pKa (strongest basic)4.83ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area9.49ChemAxon
rotatable bond count4ChemAxon
refractivity146ChemAxon
polarizability45.6ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Hiep Do, Daniel J. Spangler, Joel Rosenblatt, Barrett Remington, Onajite Okoh, “High concentration gentian violet containing medical devices and methods of making same.” U.S. Patent US20090130171, issued May 21, 2009.

US20090130171
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01046
PubChem Compound3468
PubChem Substance46505353
ChemSpider3349
PharmGKBPA449755
Drug Product Database50857
Drugs.comhttp://www.drugs.com/cons/gentian-violet-topical.html
WikipediaGentian_Violet
ATC CodesD01AE02
AHFS Codes
  • 84:04.08.92
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(77.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: yes

Actions: intercalation

Components

Name UniProt ID Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10