U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C25H30N3.HO
Molecular Weight 389.5331
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of (4-(BIS(4-(DIMETHYLAMINO)PHENYL)METHYLENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)DIMETHYLAMMONIUM HYDROXIDE

SMILES

[OH-].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=DTZKQLMCGDSBNI-UHFFFAOYSA-M
InChI=1S/C25H30N3.H2O/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;1H2/q+1;/p-1

HIDE SMILES / InChI

Description
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

Curator's Comment: Synthesis of Gentian violet was attributed French chemist Charles Lauth in 1861 under the name of ‘Violet de Paris

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
GENTIAN VIOLET

Approved Use

Topical gentian violet is used to treat some types of fungus infections inside the mouth (thrush) and of the skin.
Preventing
GENTIAN VIOLET

Approved Use

Gentian violet has weak antibacterial effects and may be used on minor cuts and scrapes to prevent infection.
Doses

Doses

DosePopulationAdverse events​
1 % single, ophthalmic
Dose: 1 %
Route: ophthalmic
Route: single
Dose: 1 %
Sources:
unhealthy, 55 years
n = 1
Health Status: unhealthy
Age Group: 55 years
Sex: F
Population Size: 1
Sources:
Other AEs: Keratoconjunctivitis...
Other AEs:
Keratoconjunctivitis
Sources:
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
Oral mucosa pain
Sources:
AEs

AEs

AESignificanceDosePopulation
Keratoconjunctivitis
1 % single, ophthalmic
Dose: 1 %
Route: ophthalmic
Route: single
Dose: 1 %
Sources:
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

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Patents

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
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).
Name Type Language
(4-(BIS(4-(DIMETHYLAMINO)PHENYL)METHYLENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)DIMETHYLAMMONIUM HYDROXIDE
Systematic Name English
METHANAMINIUM, N-(4-(BIS(4-(DIMETHYLAMINO)PHENYL)METHYLENE)-2,5-CYCLOHEXADIEN-1-YLIDENE)-N-METHYL-, HYDROXIDE (1:1)
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
252-789-8
Created by admin on Sat Dec 16 12:24:01 GMT 2023 , Edited by admin on Sat Dec 16 12:24:01 GMT 2023
PRIMARY
PUBCHEM
3015817
Created by admin on Sat Dec 16 12:24:01 GMT 2023 , Edited by admin on Sat Dec 16 12:24:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID40189484
Created by admin on Sat Dec 16 12:24:01 GMT 2023 , Edited by admin on Sat Dec 16 12:24:01 GMT 2023
PRIMARY
CAS
35919-71-2
Created by admin on Sat Dec 16 12:24:01 GMT 2023 , Edited by admin on Sat Dec 16 12:24:01 GMT 2023
PRIMARY
FDA UNII
P7K72K7GZV
Created by admin on Sat Dec 16 12:24:01 GMT 2023 , Edited by admin on Sat Dec 16 12:24:01 GMT 2023
PRIMARY