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.

Structure
Thumb
Synonyms
  • Crystal Violet
  • Crystal violet carbocation
  • Crystal violet ion(1)
  • Crystal violet(1+)
  • Gentian violet carbocation
  • Gentian violet cation
  • Gentian violet(1+)
  • Methylrosaniline
  • Methylrosanilinium
Product Ingredients
IngredientUNIICASInChI Key
Crystal violetJ4Z741D6O5548-62-9ZXJXZNDDNMQXFV-UHFFFAOYSA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
De LA Cruz Gentian VioletTincture1 g/100mLTopicalDLC Laboratories, Inc.2012-11-01Not applicableUs
Gentian Violet 2%Solution2 g/100mLTopicalThe Podiatree Company2014-10-14Not applicableUs
Gentian Violet Topical SolutionLiquid1 g/100mLTopicalLaboratorios Jaloma, S.A. de C.V.2013-09-27Not applicableUs
Gentiane Violet Liq TopLiquid1 %TopicalLaboratoire Atlas Inc1951-12-31Not applicableCanada
Humco Gentian Violet 1%Liquid10 mg/mLTopicalHumco Holding Group. Inc.2008-01-01Not applicableUs
Humco Gentian Violet 2%Liquid20 mg/mLTopicalHumco Holding Group. Inc.2008-01-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Kerr 100 Triple Dye Dispos-AGentian Violet (2.2 mg/mL) + Brilliant green (2.29 mg/mL) + Proflavine hemisulfate (1.14 mg/mL)SwabTopicalVista Pharm, Inc.2004-05-01Not applicableUs
Perineze Triple DyeGentian Violet (2.29 mg/.61mL) + Brilliant green (2.29 mg/.61mL) + Proflavine hemisulfate (1.14 mg/.61mL)SolutionTopicalPeace Medical Inc.2011-09-28Not applicableUs
Triple DyeGentian Violet (2.29 mg) + Brilliant green (2.29 mg) + Proflavine hemisulfate (1.14 mg)LiquidTopicalFrank W. Kerr Chemical Company1983-12-312004-10-27Canada
Categories
UNII
3GVJ31T6YY
CAS number
7438-46-2
Weight
Average: 372.5258
Monoisotopic: 372.243972975
Chemical Formula
C25H30N3
InChI Key
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
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

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).

Structured Indications
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.

TargetActionsOrganism
ADNA
intercalation
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB14550
KEGG Drug
D01046
PubChem Compound
3468
PubChem Substance
46505353
ChemSpider
3349
BindingDB
50052802
ChEBI
77181
ChEMBL
CHEMBL459265
PharmGKB
PA449755
HET
CVI
Drugs.com
Drugs.com Drug Page
Wikipedia
Gentian_Violet
ATC Codes
D01AE02 — MethylrosanilineG01AX09 — Methylrosaniline
AHFS Codes
  • 84:04.08.92 — Miscellaneous Antifungals
PDB Entries
1jtx / 3vw1 / 5ov9
MSDS
Download (77.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentInfection, Human Immunodeficiency Virus I1
3CompletedTreatmentOral Candidiasis1

Pharmacoeconomics

Manufacturers
  • Savage laboratories inc div altana inc
  • Key pharmaceuticals inc sub schering plough corp
Packagers
Dosage forms
FormRouteStrength
TinctureTopical1 g/100mL
SolutionTopical2 g/100mL
LiquidTopical1 g/100mL
LiquidTopical1 %
LiquidTopical10 mg/mL
LiquidTopical20 mg/mL
SwabTopical
SolutionTopical
LiquidTopical
Prices
Unit descriptionCostUnit
Gentian violet 2% solution0.16USD ml
Gentian violet 1% solution0.08USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)215 °CNot Available
water solubility4 mg/mLNot Available
logP3.18Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00193 mg/mLALOGPS
logP0.87ALOGPS
logP1.4ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.49 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity146 m3·mol-1ChemAxon
Polarizability45.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5643
Blood Brain Barrier+0.7198
Caco-2 permeable+0.6321
P-glycoprotein substrateNon-substrate0.5936
P-glycoprotein inhibitor INon-inhibitor0.6474
P-glycoprotein inhibitor IINon-inhibitor0.5747
Renal organic cation transporterNon-inhibitor0.5959
CYP450 2C9 substrateNon-substrate0.7272
CYP450 2D6 substrateNon-substrate0.7573
CYP450 3A4 substrateSubstrate0.5753
CYP450 1A2 substrateInhibitor0.5787
CYP450 2C9 inhibitorNon-inhibitor0.8225
CYP450 2D6 inhibitorNon-inhibitor0.5732
CYP450 2C19 inhibitorNon-inhibitor0.8028
CYP450 3A4 inhibitorNon-inhibitor0.667
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7973
Ames testNon AMES toxic0.9132
CarcinogenicityCarcinogens 0.8444
BiodegradationNot ready biodegradable0.9944
Rat acute toxicity2.5102 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9172
hERG inhibition (predictor II)Non-inhibitor0.7075
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Dialkylarylamines / Aniline and substituted anilines / Secondary ketimines / Azomethines / Organopnictogen compounds / Hydrocarbon derivatives / Organic cations
Substituents
Diphenylmethane / Aniline or substituted anilines / Dialkylarylamine / Tertiary aliphatic/aromatic amine / Secondary ketimine / Azomethine / Tertiary amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
iminium ion (CHEBI:77181)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
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:17139284]
  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:17016423]
  3. Docampo R, Moreno SN: The metabolism and mode of action of gentian violet. Drug Metab Rev. 1990;22(2-3):161-78. [PubMed:2272286]
  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:16499061]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
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:12606755]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2017 19:22