gentian violet

Trade name: genapax

Small moleculeapproved

Approved

Feb 2, 1977

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. — NCATS

Clinical trial activity

4 trials · 10 clinical orgs · 2 marketing orgs

Phase 1
0
Phase 2
4
Phase 3
2
Phase 4
0

Earliest trial started Nov 1, 2002 (NCT00128323)

Timeline

1860s

  1. Jun 1, 1866

    Evidence of US Marketing

1970s

  1. Feb 2, 1977

    Key Pharmaceuticals — Earliest FDA Approval

  2. Feb 2, 1977

    Key Pharmaceuticals — Marketing Organization

  3. Feb 2, 1977

    Key Pharmaceuticals — NDA Organization

2000s

  1. Jan 1, 2002

    Earliest Phase 3 Sponsor(trial)

2020s

  1. Jan 1, 2020

    Earliest Phase 2 Sponsor(trial)

Indications

Mechanism of action

  • DNAINHIBITOR

    DNA inhibitor

    Generates free radicals causing DNA damage.

Approval history

  • approvedFeb 2, 1977
  • approvedJun 1, 1866

Chemistry & pharmacology

Loading structure…

SMILES

CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccc(N(C)C)cc2)cc1
Mol. weight
372.54 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Topical
Availability
Discontinued

Oral

No

Parenteral

No

Topical

Yes

Sources

Also known as

  • crystal violet
  • crystal violet
  • crystal violet
  • crystal violet
  • crystal violet(1+)
  • crystal violet(1+)
  • crystal violet base
  • crystal violet carbinol
  • crystal violet carbocation
  • crystal violet carbocation
  • crystal violet ion(1)
  • crystal violet ion(1)
  • genapax
  • genapax
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet
  • gentian violet(1+)
  • gentian violet(1+)
  • gentian violet carbocation
  • gentian violet carbocation
  • gentian violet cation
  • gentian violet cation
  • gentium violet
  • gnf-pf-880
  • gnf-pf-880
  • gv 11
  • gvs
  • gvs
  • methylrosaniline
  • methylrosaniline
  • methylrosaniline
  • methylrosaniline
  • methylrosaniline
  • methylrosaniline chloride
  • methylrosaniline chloride
  • methylrosaniline chloride
  • methylrosaniline chloride
  • methylrosaniline chloride
  • methylrosaniline chloride
  • methylrosaniline cl
  • methylrosanilinium
  • methylrosanilinium
  • methylrosanilinium chloride
  • methylrosanilinium chloride
  • methylrosanilinium cl
  • methyl violet
  • methyl violet
  • pyoktanin
  • pyoktanin
  • viocid
  • viocid

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT04354012Phase 2Jun 30, 2020Wake Forest University
NCT04388163Phase 2Jun 30, 2020Wake Forest University
NCT01427738Phase 3Jun 1, 2011AIDS Clinical Trials Group, Case Western Reserve University, Eastman Dental Hospital, Joint Clinical Research Centre, Kampala, Uganda, National AIDS Research Institute, Pune, National Institute of Allergy and Infectious Diseases (NIAID), Parirenyatwa Hospital
NCT00128323Phase 3Nov 1, 2002British Society for Antimicrobial Chemotherapy, University of Malawi
Showing 4 of 4 trials
Page 1 / 1

Organizations

Research & Development (10)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Wake Forest UniversityAcademic/Hospital2212020
AIDS Clinical Trials GroupAcademic/Hospital1112011
British Society for Antimicrobial ChemotherapyAcademic/Hospital1012002
Case Western Reserve UniversityAcademic/Hospital1012011
Eastman Dental HospitalAcademic/Hospital1012011
Joint Clinical Research Centre, Kampala, UgandaAcademic/Hospital1012011
National AIDS Research Institute, PuneAcademic/Hospital1012011
National Institute of Allergy and Infectious Diseases (NIAID)Government1012011
Parirenyatwa HospitalAcademic/Hospital1012011
University of MalawiAcademic/Hospital1112002
10 organizations
Page 1 / 1

Marketing (3)

OrganizationOrg typeRelationshipDate
Key PharmaceuticalsFor profitMKTGFeb 2, 1977
Key PharmaceuticalsFor profitNDAFeb 2, 1977
Savage LabsFor profitMKTG