Details
Stereochemistry | ACHIRAL |
Molecular Formula | C25H30N3.Cl |
Molecular Weight | 407.979 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].CN(C)C1=CC=C(C=C1)C(C2=CC=C(C=C2)N(C)C)=C3C=CC(C=C3)=[N+](C)C
InChI
InChIKey=ZXJXZNDDNMQXFV-UHFFFAOYSA-M
InChI=1S/C25H30N3.ClH/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;1H/q+1;/p-1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C25H30N3 |
Molecular Weight | 372.5258 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24118276 | http://www.webmd.com/drugs/2/drug-4397/gentian-violet-topical/detailsCurator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00406
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24118276 | http://www.webmd.com/drugs/2/drug-4397/gentian-violet-topical/details
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00406
Gentian violet ((GV) hexamethyl pararosaniline, also known as crystal violet, methyl violet) is a triphenylmethane dye with anti-bacterial, anti-fungal, anti-helminithic, anti-trypanosomal, anti-angiogenic and anti-tumor properties. GV has a lengthy history and has been used successfully as monotherapy and an adjunct to treatment in a variety of diseases. Gentian violet 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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24118276
Curator's Comment: Synthesis of Gentian violet was attributed French chemist Charles Lauth in 1861 under the name of ‘Violet de Paris
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2366922 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18579783 |
22.13 nM [EC50] | ||
Target ID: CHEMBL2364041 |
|||
Target ID: CHEMBL368 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21478242 |
30.6 µM [IC50] | ||
Target ID: CHEMBL2364041 |
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Target ID: Thioredoxin reductase 2, fungal Sources: https://www.ncbi.nlm.nih.gov/pubmed/24118276 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | GENTIAN VIOLET Approved UseTopical gentian violet is used to treat some types of fungus infections inside the mouth (thrush) and of the skin. |
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Preventing | GENTIAN VIOLET Approved UseGentian violet has weak antibacterial effects and may be used on minor cuts and scrapes to prevent infection. |
Doses
Dose | Population | Adverse events |
---|---|---|
1 % single, ophthalmic |
unhealthy, 55 years n = 1 Health Status: unhealthy Age Group: 55 years Sex: F Population Size: 1 Sources: |
Other AEs: Keratoconjunctivitis... |
2 % 10 times / day multiple, oral Dose: 2 %, 10 times / day Route: oral Route: multiple Dose: 2 %, 10 times / day Sources: |
unhealthy, infant n = 1 Health Status: unhealthy Age Group: infant Population Size: 1 Sources: |
Disc. AE: Swollen tongue, Oral mucosa pain... AEs leading to discontinuation/dose reduction: Swollen tongue Sources: Oral mucosa pain |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Keratoconjunctivitis | 1 % single, ophthalmic |
unhealthy, 55 years n = 1 Health Status: unhealthy Age Group: 55 years Sex: F Population Size: 1 Sources: |
|
Oral mucosa pain | Disc. AE | 2 % 10 times / day multiple, oral Dose: 2 %, 10 times / day Route: oral Route: multiple Dose: 2 %, 10 times / day Sources: |
unhealthy, infant n = 1 Health Status: unhealthy Age Group: infant Population Size: 1 Sources: |
Swollen tongue | Disc. AE | 2 % 10 times / day multiple, oral Dose: 2 %, 10 times / day Route: oral Route: multiple Dose: 2 %, 10 times / day Sources: |
unhealthy, infant n = 1 Health Status: unhealthy Age Group: infant Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Activation 15 uM] | ||||
yes [Activation 2 uM] | ||||
yes [Activation 3.2 uM] | ||||
yes [Activation 3.9 uM] | ||||
yes [Activation 6.3 uM] | ||||
yes [Activation 7.6 uM] | ||||
yes [Activation 7.9 uM] | ||||
yes [IC50 7.7 uM] | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/23611293/ |
Sample Use Guides
Clean the affected area and apply a small amount of this product on the
area 1 to 3 times daily. May be covered with a sterile bandage.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18242063
Gentian violet showed the most potent activity against all Candida isolates tested (MIC range, MIC for 50% of the organisms (MIC(50)) and MIC for 90% of the organisms (MIC(90)) of 0.03-0.25 ug/mL, 0.06 ug/mL and 0.1 2 ug/mL, respectively).
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 15:54:31 UTC 2023
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on
Sat Dec 16 15:54:31 UTC 2023
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Record UNII |
J4Z741D6O5
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C461
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EPA PESTICIDE CODE |
39502
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CFR |
21 CFR 589.1000
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Code System | Code | Type | Description | ||
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D005840
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11057
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100000080908
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4366
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208-953-6
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GENTIAN VIOLET
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PRIMARY | Other names: Crystal violet, gentian violet. Description: A dark green powder or greenish, glistening pieces having a metallic lustre; odourless or almost odourless. Solubility: Sparingly soluble in water; soluble in ethanol (~750 g/l) TS and glycerol R; practically insoluble in ether R. Category: Anti-infective drug. Storage: Methylrosanilinium chloride should be kept in a tightly closed container, protected from light. Requirements: Methylrosanilinium chloride contains not less than 96.0% and not more than the equivalent of 101.0% of C25H30ClN3, calculated with reference to the anhydrous substance. | ||
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DTXSID5020653
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4138
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m5700
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113
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CHEMBL459265
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SUB08875MIG
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Gentian Violet
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41688
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C548657
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CRYSTAL VIOLET
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DBSALT000604
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4778
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C61776
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3090
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1290002
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J4Z741D6O5
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J4Z741D6O5
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548-62-9
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |