Gentian Violet Solution 1 W V Use

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

Structure for Gentian violet cation (DB00406)

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).

Pharmacology

Reduce drug development failure rates

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Associated Conditions

Bacterial Infection of the umbilical cord area
Fungal Infection of the umbilical cord area
Infection
Infections, Fungal

Contraindications & Blackbox Warnings

Contraindications

Avoid life-threatening adverse drug events

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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.

Target	Actions	Organism
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

Adverseeffects

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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

Products2

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dosage, form, labeller, route of administration, and marketing period.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Gentian violet	J4Z741D6O5	548-62-9	ZXJXZNDDNMQXFV-UHFFFAOYSA-M

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
De LA Cruz Gentian Violet	Tincture	1 g/100mL	Topical	DLC Laboratories, Inc.	2012-11-01	Not applicable
Gentian Violet 1%	Liquid	10 mg/1mL	Topical	Humco Holding Group, Inc.	2008-01-01	Not applicable
Gentian Violet 2%	Solution	2 g/100mL	Topical	The Podiatree Company	2014-10-14	Not applicable
Gentian Violet Anti-Infective	Liquid	10 mg/1mL	Topical	Germa Products, LLC	2021-03-29	Not applicable
Gentian Violet Topical Solution	Liquid	1 g/100mL	Topical	Laboratorios Jaloma, S.A. de C.V.	2013-09-27	Not applicable
Gentiane Violet Liq Top	Liquid	1 %	Topical	Laboratoire Atlas Inc	1951-12-31	2019-05-10
GNP Gentian Violet 1%	Liquid	10 mg/1mL	Topical	Amerrisource Bergen	2008-01-01	Not applicable
Humco Gentian Violet 1%	Liquid	10 mg/1mL	Topical	Humco Holding Group, Inc.	2008-01-01	Not applicable
Humco Gentian Violet 2%	Liquid	20 mg/1mL	Topical	Humco Holding Group, Inc.	2008-01-01	Not applicable
ยากวาดลิ้น ตราจระเข้บิน	Solution	1 g/100ml	Topical	บริษัท โรงงานเภสัชอุตสาหกรรม เจเอสพี (ประเทศไทย) จำกัด (มหาชน)	1986-11-07	2020-09-29

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Kerr 100 Triple Dye Dispos-A	Gentian violet (2.2 mg/1mL) + Brilliant green (2.29 mg/1mL) + Proflavine hemisulfate (1.14 mg/1mL)	Swab	Topical	Vistapharm, Inc.	2004-05-01	Not applicable
Perineze Triple Dye	Gentian violet (2.29 mg/0.61mL) + Brilliant green (2.29 mg/0.61mL) + Proflavine hemisulfate (1.14 mg/0.61mL)	Solution	Topical	Peace Medical Inc.	2011-09-28	Not applicable
Triple Dye	Gentian violet (2.29 mg / mL) + Brilliant green (2.29 mg / mL) + Proflavine hemisulfate (1.14 mg / mL)	Liquid	Topical	Frank W. Kerr Chemical Company	1983-12-31	2004-10-27

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

External Links

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

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Completed	Treatment	Human Immunodeficiency Virus Type 1 (HIV-1) Infection	1
3	Completed	Treatment	Oral Candidiasis	1
2	Not Yet Recruiting	Treatment	Hidradenitis Suppurativa (HS)	2

Pharmacoeconomics

Manufacturers

Savage laboratories inc div altana inc
Key pharmaceuticals inc sub schering plough corp

Packagers

Humco

Dosage Forms

Form	Route	Strength
Solution	Oral
Tincture	Topical	1 g/100mL
Solution	Topical	2 g/100mL
Liquid	Topical	1 g/100mL
Liquid	Topical	1 %
Liquid	Topical	10 mg/1mL
Liquid	Topical	20 mg/1mL
Swab	Topical
Solution	Topical
Liquid	Topical
Solution	Topical
Solution	Topical	1 g/100ml
Solution	Topical	0.5 g/100ml

Prices

Unit description	Cost	Unit
Gentian violet 2% solution	0.16USD	ml
Gentian violet 1% solution	0.08USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	215 °C	Not Available
water solubility	4 mg/mL	Not Available
logP	3.18	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00193 mg/mL	ALOGPS
logP	0.87	ALOGPS
logP	1.4	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	4.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	146 m³·mol^-1	ChemAxon
Polarizability	45.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.5643
Blood Brain Barrier	+	0.7198
Caco-2 permeable	+	0.6321
P-glycoprotein substrate	Non-substrate	0.5936
P-glycoprotein inhibitor I	Non-inhibitor	0.6474
P-glycoprotein inhibitor II	Non-inhibitor	0.5747
Renal organic cation transporter	Non-inhibitor	0.5959
CYP450 2C9 substrate	Non-substrate	0.7272
CYP450 2D6 substrate	Non-substrate	0.7573
CYP450 3A4 substrate	Substrate	0.5753
CYP450 1A2 substrate	Inhibitor	0.5787
CYP450 2C9 inhibitor	Non-inhibitor	0.8225
CYP450 2D6 inhibitor	Non-inhibitor	0.5732
CYP450 2C19 inhibitor	Non-inhibitor	0.8028
CYP450 3A4 inhibitor	Non-inhibitor	0.667
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.7973
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Carcinogens	0.8444
Biodegradation	Not ready biodegradable	0.9944
Rat acute toxicity	2.5102 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9172
hERG inhibition (predictor II)	Non-inhibitor	0.7075

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

Drugtargets2

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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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]
Docampo R, Moreno SN: The metabolism and mode of action of gentian violet. Drug Metab Rev. 1990;22(2-3):161-78. [Article]
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 December 03, 2021 01:12

Gentian Violet Solution 1 W V Use

Source: https://go.drugbank.com/drugs/DB00406

Gentian Violet Solution 1 W V Use

Identification

Structure for Gentian violet cation (DB00406)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

Transporters

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