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Showing drug card for Gentian Violet (DB00406)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:05:45
Primary Accession Number DB00406
Secondary Accession Number
  • APRD00998
Name Gentian Violet
Drug Type
  • Approved
  • Small Molecule
Description A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties. [PubChem]
Synonyms
  1. Crystal Violet
Brand Names
  1. Adergon
  2. Aizen Crystal Violet
  3. Aizen Crystal Violet Extra Pure
  4. Aniline Violet
  5. Aniline Violet pyoktanine
  6. Atmonil
  7. Avermin
  8. Axuris
  9. Badil
  10. Basic Violet 3
  11. Basic Violet BN
  12. Basic Violet-3
  13. Bismuth Violet
  14. Brilliant Violet 5B
  15. C.I. Basic Violet 3
  16. Calcozine Violet 6BN
  17. Calcozine Violet C
  18. Crystal Violet 10B
  19. Crystal Violet 5BO
  20. Crystal Violet 6B
  21. Crystal Violet 6BO
  22. Crystal Violet AO
  23. Crystal Violet AON
  24. Crystal Violet BP
  25. Crystal Violet BPC
  26. Crystal Violet Extra Pure
  27. Crystal Violet Extra Pure APN
  28. Crystal Violet Extra Pure APNX
  29. Crystal Violet FN
  30. Crystal Violet HL2
  31. Crystal Violet O
  32. Crystal Violet Pure DSC
  33. Crystal Violet Pure DSC Brilliant
  34. Crystal Violet SS
  35. Crystal Violet Technical
  36. Crystal Violet USP
  37. Crystal Violet base
  38. Crystal Violet chloride
  39. Crystal Violet chloride salt
  40. GV-Eleven
  41. Genapax
  42. Gentersal
  43. Gentiaverm
  44. Genticid
  45. Gentioletten
  46. Gvs
  47. Hecto Violet R
  48. Hectograph Violet SR
  49. Hexamethyl Violet
  50. Hexamethylpararosaniline chloride
  51. Hidaco Brilliant Crystal Violet
  52. Hidaco crystal Violet
  53. Meroxyl-Wander
  54. Meroxylan-Wander
  55. Methyl Violet 10B
  56. Methyl Violet 10BD
  57. Methyl Violet 10BK
  58. Methyl Violet 10BN
  59. Methyl Violet 10BNS
  60. Methyl Violet 10BO
  61. Methyl Violet 5BNO
  62. Methyl Violet 5BO
  63. Methyl Violet 6B
  64. Methyl violet
  65. Methylrosaniline chloride
  66. Mitsui Crystal Violet
  67. Oxiuran
  68. Oxycolor
  69. Oxyozyl
  70. Paper Blue R
  71. Plastoresin Violet 5BO
  72. Pyoktanin
  73. Vermicid
  74. Vianin
  75. Viocid
  76. Violet 5BO
  77. Violet 6BN
  78. Violet CP
  79. Violet XXIII
  80. crystal violet for microscopy
  81. gentian violet gr
  82. gention violet alchoholic staining solution
  83. methylrosanilinium chloride
Brand Mixtures
  1. Blu Kote Dr Naylors (Acriflavine + Gentian Violet + Glycerine + Isopropyl Alcohol + Sodium Propionate + Urea)
  2. Blue Lotion (Gentian Violet + Methylene Blue + Tannic Acid)
  3. Co-Op Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate))
  4. Cristisol (Acriflavine + Gentian Violet + Isopropyl Alcohol)
  5. Pink Eye Guard (Allantoin + Boric Acid + Gentian Violet)
  6. Pink Eye Spray (Furfural + Gentian Violet + Isopropyl Alcohol + Methylene Blue + Phenylmercuric Nitrate (Basic) + Tetrahydrofurfuryl Alcohol + Urea)
  7. Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate))
  8. Triple Dye (Brilliant Green + Gentian Violet + Proflavine Hemisulfate)
  9. Wound & Pinkeye Spray (Gentian Violet + Neomycin (Neomycin Sulfate))
  10. Wound Kote Gentian Violet Spray Wound Dre (Acriflavine + Furfural + Methyl Violet + Sodium Propionate + Urea)
Chemical IUPAC Name [4-[bis(4-dimethylaminophenyl)methylidene]-1-cyclohexa-2,5-dienylidene]-dimethylazanium
Chemical Formula C25H30N3
Chemical Structure Structure
CAS Registry Number 14426-25-6
InChI Identifier InChI=1/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
InChI Key LGLFFNDHMLKUMI-UHFFFAOYAV
KEGG Drug D01046 Link Image
KEGG Compound Not Available
PubChem Compound 3468 Link Image
PubChem Substance 538591 Link Image
ChEBI ID Not Available
PharmGKB ID PA449755 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00050857 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Gentian_Violet Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 372.5258
Monoisotopic Molecular Weight 372.2440
State Solid
Melting Point 215 oC
Experimental Water Solubility 4 mg/mL Source: PhysProp
Predicted Water Solubility 1.93e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.18 Source: PhysProp
Predicted LogP 0.87 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.32 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN(C)C1=CC=C(C=C1)C(\C1=CC=C(C=C1)N(C)C)=C1\C=C/C(/C=C\1)=[N+](\C)C
Canonical SMILES CN(C)C1=CC=C(C=C1)C(C1=CC=C(C=C1)N(C)C)=C1C=CC(C=C1)=[N+](C)C
Drug Category
  • Anti-Infective Agents, Local
ATC Codes
AHFS Codes
  • 84:04.08.92
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).
Pharmacology 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
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.
Protein Binding Not Available
Biotransformation Primarily hepatic, mostly demethylation
Half Life Not Available
Dosage Forms
Form Route
Liquid Topical
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected
  • Bacteria and protozoa
  • Yeast and other fungi
Targets
  1. DNA
Drug Target 1 [top]
Target 1 ID 874
Target 1 Name DNA
Target 1 Synonyms
  1. Deoxyribonucleic acid
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 7656 (double strand)
Target 1 Theoretical pI Not Available
Target 1 GO Classification
Function
information storage
information transfer
Process
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
Component
cell
intracellular
nucleus
mitochondria
Target 1 General Function Biological information storage and information transfer
Target 1 Specific Function 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.
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
RNA polymerase map03020 Link Image
Target 1 Reactions
  • DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
Target 1 Pfam Domain Function Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID 1BNA Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus and mitochondria
Target 1 Gene Sequence >Example: Dickerson dodecamer 
CGCGAATTCGCG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus All loci
Target 1 SNPs Not Available
Target 1 General References
  1. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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.