Gentian Violet

Identification

Summary

Gentian Violet is an antiseptic violet dye used to prevent various infections, including fungal and bacterial infections.

Generic Name
Gentian violet cation
Commonly known or available as Gentian Violet
DrugBank Accession Number
DB00406
Background

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

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 372.5258
Monoisotopic: 372.243972975
Chemical Formula
C25H30N3
Synonyms
  • Crystal Violet
  • Crystal violet carbocation
  • Crystal violet ion(1)
  • Crystal violet(1+)
  • Gentian violet carbocation
  • Gentian violet cation
  • Gentian violet(1+)
  • Methylrosaniline
  • Methylrosanilinium

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).

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for prophylaxis ofBacterial infection of the umbilical cord areaCombination Product in combination with: Proflavine (DB01123), Brilliant green cation (DB11279)••• •••••••••••
Treatment ofFungal infection••• •••
Used in combination for prophylaxis ofFungal infection of the umbilical cord areaCombination Product in combination with: Brilliant green cation (DB11279), Proflavine (DB01123)••• •••••••••••
Prophylaxis ofInfection••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
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

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Gentian violetJ4Z741D6O5548-62-9ZXJXZNDDNMQXFV-UHFFFAOYSA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
De LA Cruz Gentian VioletTincture1 g/100mLTopicalDLC Laboratories, Inc.2012-11-01Not applicableUS flag
El Valle Gentian VioletLiquid10 mg/1mLTopicalPharmadel LLC2023-05-31Not applicableUS flag
Gentian VioletLiquid0.1 g/100gTopicalSANVALL ENTERPRISES, INC2021-09-02Not applicableUS flag
Gentian Violet 1%Liquid10 mg/1mLTopicalPharma Nobis, LLC2008-01-01Not applicableUS flag
Gentian Violet 1%Liquid10 mg/1mLTopicalHumco Holding Group, Inc.2008-01-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AMARO MEDICINALE GIULIANIGentian violet cation (111 mg/100g) + Boldo leaf extract (100 mg/100g) + Frangula purshiana bark (121 mg/100g) + Rhubarb (356 mg/100g)SolutionOralGiuliani Spa2014-07-08Not applicableItaly flag
AMARO MEDICINALE GIULIANIGentian violet cation (111 mg/100g) + Boldo leaf extract (100 mg/100g) + Frangula purshiana bark (121 mg/100g) + Rhubarb (356 mg/100g)SolutionOralGiuliani Spa2014-07-08Not applicableItaly flag
AMARO MEDICINALE GIULIANIGentian violet cation (111 mg/100g) + Boldo leaf extract (100 mg/100g) + Frangula purshiana bark (121 mg/100g) + Rhubarb (356 mg/100g)SolutionOralGiuliani Spa2014-07-08Not applicableItaly flag
AMARO MEDICINALE GIULIANIGentian violet cation (111 mg/100g) + Boldo leaf extract (100 mg/100g) + Frangula purshiana bark (121 mg/100g) + Rhubarb (356 mg/100g)SolutionOralGiuliani Spa2014-07-08Not applicableItaly flag
AMARO MEDICINALE GIULIANIGentian violet cation (111 mg/100g) + Boldo leaf extract (100 mg/100g) + Frangula purshiana bark (121 mg/100g) + Rhubarb (356 mg/100g)SolutionOralGiuliani Spa2014-07-08Not applicableItaly flag

Categories

ATC Codes
G01AX09 — MethylrosanilineD01AE02 — Methylrosaniline
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Aniline or substituted anilines / Aromatic homomonocyclic compound / Azomethine / Dialkylarylamine / Diphenylmethane / Hydrocarbon derivative / Organic cation / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
iminium ion (CHEBI:77181)
Affected organisms
  • Yeast and other fungi
  • Bacteria and protozoa

Chemical Identifiers

UNII
3GVJ31T6YY
CAS number
7438-46-2
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

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
Human Metabolome Database
HMDB0014550
KEGG Drug
D01046
PubChem Compound
3468
PubChem Substance
46505353
ChemSpider
3349
BindingDB
50052802
RxNav
1546369
ChEBI
77181
ChEMBL
CHEMBL459265
ZINC
ZINC000013763987
PharmGKB
PA449755
PDBe Ligand
CVI
Drugs.com
Drugs.com Drug Page
Wikipedia
Gentian_Violet
PDB Entries
1jtx / 3vw1 / 5ov9 / 5vlm / 6pub
MSDS
Download (77.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
3CompletedTreatmentOral Candidiasis1
2Active Not RecruitingTreatmentHidradenitis Suppurativa (HS)1
2Not Yet RecruitingTreatmentHidradenitis Suppurativa (HS)1

Pharmacoeconomics

Manufacturers
  • Savage laboratories inc div altana inc
  • Key pharmaceuticals inc sub schering plough corp
Packagers
  • Humco
Dosage Forms
FormRouteStrength
SolutionOral
TinctureTopical1 g/100mL
LiquidTopical0.1 g/100g
SolutionTopical2 g/100mL
LiquidTopical1 g/100mL
LiquidTopical1 %
LiquidTopical10 mg/1mL
LiquidTopical20 mg/1mL
SwabTopical
SolutionTopical
LiquidTopical
SolutionTopical10 ml
SolutionTopical1 g/100ml
SolutionTopical0.5 g/100ml
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-MSsplash10-0pi0-3049000000-80f825970014ad316343
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-225.2231279
predicted
DarkChem Lite v0.1.0
[M-H]-224.4998279
predicted
DarkChem Lite v0.1.0
[M-H]-203.25902
predicted
DeepCCS 1.0 (2019)
[M+H]+225.3893279
predicted
DarkChem Lite v0.1.0
[M+H]+225.7925279
predicted
DarkChem Lite v0.1.0
[M+H]+205.65459
predicted
DeepCCS 1.0 (2019)
[M+Na]+224.4933279
predicted
DarkChem Lite v0.1.0
[M+Na]+224.9508279
predicted
DarkChem Lite v0.1.0
[M+Na]+211.68385
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Nucleotide
Organism
Humans
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.
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. [Article]
  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. [Article]
  3. Docampo R, Moreno SN: The metabolism and mode of action of gentian violet. Drug Metab Rev. 1990;22(2-3):161-78. [Article]
  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. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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

Drug created at June 13, 2005 13:24 / Updated at March 28, 2024 03:23