gentian violet
Trade name: genapax
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
Earliest trial started Nov 1, 2002 (NCT00128323)
Timeline
1860s
- Jun 1, 1866
Evidence of US Marketing
1970s
- Feb 2, 1977
Key Pharmaceuticals — Earliest FDA Approval
- Feb 2, 1977
Key Pharmaceuticals — Marketing Organization
- Feb 2, 1977
Key Pharmaceuticals — NDA Organization
2000s
- Jan 1, 2002
Earliest Phase 3 Sponsor(trial)
2020s
- Jan 1, 2020
Earliest Phase 2 Sponsor(trial)
Indications
Approved for
Mechanism of action
- DNAINHIBITOR
DNA inhibitor
Generates free radicals causing DNA damage.
Approval history
- approvedFeb 2, 1977
- approvedJun 1, 1866
Chemistry & pharmacology
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
- ChEMBLCHEMBL459265 ↗
- WikipediaCrystal violet ↗
- NCATS3GVJ31T6YY ↗
- ChEMBLCHEMBL64894 ↗
- ChEMBLCHEMBL592105 ↗
- ChEMBLCHEMBL2105250 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT04354012 | Phase 2 | Jun 30, 2020 | Wake Forest University |
| NCT04388163 | Phase 2 | Jun 30, 2020 | Wake Forest University |
| NCT01427738 | Phase 3 | Jun 1, 2011 | AIDS 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 |
| NCT00128323 | Phase 3 | Nov 1, 2002 | British Society for Antimicrobial Chemotherapy, University of Malawi |
Organizations
Research & Development (10)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Wake Forest University | Academic/Hospital | 2 | 2 | 1 | 2020 |
| AIDS Clinical Trials Group | Academic/Hospital | 1 | 1 | 1 | 2011 |
| British Society for Antimicrobial Chemotherapy | Academic/Hospital | 1 | 0 | 1 | 2002 |
| Case Western Reserve University | Academic/Hospital | 1 | 0 | 1 | 2011 |
| Eastman Dental Hospital | Academic/Hospital | 1 | 0 | 1 | 2011 |
| Joint Clinical Research Centre, Kampala, Uganda | Academic/Hospital | 1 | 0 | 1 | 2011 |
| National AIDS Research Institute, Pune | Academic/Hospital | 1 | 0 | 1 | 2011 |
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 1 | 0 | 1 | 2011 |
| Parirenyatwa Hospital | Academic/Hospital | 1 | 0 | 1 | 2011 |
| University of Malawi | Academic/Hospital | 1 | 1 | 1 | 2002 |
Marketing (3)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Key Pharmaceuticals | For profit | MKTG | Feb 2, 1977 |
| Key Pharmaceuticals | For profit | NDA | Feb 2, 1977 |
| Savage Labs | For profit | MKTG | — |