tioconazole
Trade name: tz-3
Approved
Feb 18, 1983
Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. Tioconazole is a broad-spectrum imidazole antifungal agent that inhibits the growth of human pathogenic yeasts. Tioconazole exhibits fungicidal activity in vitro against Candida albicans, other species of the genus Candida, and against Torulopsis glabrata. Tioconazole prevents the growth and function of some fungal organisms by interfering with the production of substances needed to preserve the cell membrane. This drug is effective only for infections caused by fungal organisms. Tioconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Tioconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel. Side effects (for the women's formulas) may include temporary burning/irritation of the vaginal area, moderate drowsiness, headache similar to a sinus headache, hives, and upper respiratory infection. — NCATS
Clinical trial activity
3 trials · 4 clinical orgs · 3 marketing orgs
Earliest trial started Apr 30, 2019 (NCT03839875)
Timeline
1990s
- Feb 11, 1997
Bristol-Myers Squibb — NDA Secondary Org
2000s
- Nov 21, 2001
Perrigo — Marketing Organization
2020s
- Jan 1, 2020
Earliest Phase 3 Sponsor(trial)
Indications
Approved for
Mechanism of action
- Cytochrome P450 51INHIBITOR
ERG11 inhibitor
Approval history
- approvedFeb 18, 1983
Chemistry & pharmacology
SMILES
ClC1=C(COC(CN2C=CN=C2)C3=CC=C(Cl)C=C3Cl)C=CS1- Mol. weight
- 387.711 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Topical
- Availability
- Over the Counter
Oral
No
Parenteral
No
Topical
Yes
Sources
- WikipediaTioconazole ↗
- NCATSS57Y5X1117 ↗
- ChEMBLCHEMBL1200438 ↗
Also known as
- 1h-imidazole, 1-(2-((2-chloro-3-thienyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-
- gyno-trosyd
- monistat 1-day
- mykontral
- tioconazol
- tioconazol
- tioconazole
- tioconazole
- tioconazole
- tioconazole
- tioconazole
- tioconazole
- tioconazole
- tioconazole
- tioconazole
- tioconazolum
- tioconazolum
- trosderm
- trosid
- trosyd
- trosyl
- trosyl
- trosyl
- tz-3
- tz-3
- tz-3
- uk 20,349
- uk-20349
- uk-20349
- uk-20349
- uk-20,349
- uk-20,349
- uk-20,349
- uk-20,349
- uk-20,349
- vagistat
- vagistat
- vagistat
- vagistat-1
- vagistat-1
- vagistat-1
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05999474 | Phase 4 | Sep 1, 2022 | Cairo University |
| NCT06056947 | Phase 3 | Jul 20, 2020 | Ege University, Exeltis, MonitorCRO |
| NCT03839875 | Phase 4 | Apr 30, 2019 | Exeltis, MonitorCRO |
Organizations
Research & Development (4)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Exeltis | For profit | 2 | 1 | 2 | 2019 |
| MonitorCRO | For profit | 2 | 0 | 2 | 2019 |
| Cairo University | Academic/Hospital | 1 | 1 | 1 | 2022 |
| Ege University | Academic/Hospital | 1 | 1 | 1 | 2020 |
Marketing (3)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Bristol-Myers Squibb | For profit | NDA2 | Feb 11, 1997 |
| Perrigo | For profit | MKTG | Nov 21, 2001 |
| Pfizer | For profit | NDA | Feb 18, 1983 |