butoconazole
Trade name: Femstat
Approved
Nov 25, 1985
Butoconazole, trade names Gynazole-1, an imidazole antifungal used in gynecology for the local treatment of vulvovaginal candidiasis (infections caused by Candida). The exact mechanism of the antifungal action of butoconazole nitrate is unknown; however, it is presumed to function as other imidazole derivatives via inhibition of steroid synthesis. Imidazoles generally inhibit the conversion of lanosterol to ergosterol, resulting in a change in fungal cell membrane lipid composition. This structural change alters cell permeability and, ultimately, results in the osmotic disruption or growth inhibition of the fungal cell. — NCATS
Clinical trial activity
4 trials · 3 clinical orgs · 5 marketing orgs
Earliest trial started Jan 1, 2008 (NCT00616330)
Timeline
1980s
- Nov 25, 1985
Earliest FDA Approval
1990s
- Dec 21, 1995
Bayer — NDA Secondary Org
- Feb 7, 1997
Perrigo — NDA Secondary Org
- Feb 7, 1997
Padagis Us — Marketing Organization
- Feb 7, 1997
Padagis Us — NDA Secondary Org
2000s
- Jan 1, 2008
Earliest Phase 3 Sponsor(trial)
2010s
- May 18, 2012
Perrigo — Marketing Organization
2020s
- Jan 1, 2022
Earliest Phase 2 Sponsor(trial)
Indications
Approved for
Mechanism of action
- Cytochrome P450 51INHIBITOR
ERG11 inhibitor
Approval history
- approvedNov 25, 1985
Chemistry & pharmacology
SMILES
Clc1ccc(CCC(Cn2ccnc2)Sc2c(Cl)cccc2Cl)cc1- Mol. weight
- 411.79 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Topical
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
Yes
Sources
- ChEMBLCHEMBL1295 ↗
- WikipediaButoconazole ↗
- NCATS0Q771797PH ↗
- ChEMBLCHEMBL1200398 ↗
Also known as
- 1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl)-1h-imidazole
- 1h-imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-,
- alant starch
- aventis brand of butoconazole nitrate
- bayer brand 1 of butoconazole nitrate
- bayer brand 2 of butoconazole nitrate
- butaconazole
- butaconazole
- butaconazole
- butaconazole nitrate
- butoconazol
- butoconazol
- butoconazole
- butoconazole
- butoconazole
- butoconazole
- butoconazole
- butoconazole
- butoconazole
- butoconazole
- butoconazole
- butoconazole
- butoconazole nitrate
- butoconazole nitrate
- butoconazole nitrate
- butoconazole nitrate
- butoconazole nitrate
- butoconazole nitrate
- butoconazolum
- butoconazolum
- compositenstärke
- compositenstärke
- dahlin
- dahlin
- femstal
- femstat
- femstat
- femstat
- femstat
- femstat
- femstat 3
- femstat 3
- gynazole
- gynazole-1
- gynazole-1
- gynazole-1
- gynomyk
- mycelex-3
- polyfructosanum
- polyfructosanum
- rs 35887
- rs-35887
- rs-35887
- rs-35887-00-10-3
- rs-35887-00-10-3
- syntex brand of butoconazole nitrate
- ther-rx brand of butoconazole nitrate
- will brand of butoconazole nitrate
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05031481 | Phase 2 | Jul 31, 2022 | EMS S/A |
| NCT00694928 | Phase 3 | May 1, 2008 | Lumara Health |
| NCT01039584 | N/A | Feb 1, 2008 | Perrigo |
| NCT00616330 | Phase 3 | Jan 1, 2008 | Lumara Health |
Organizations
Research & Development (3)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Lumara Health | For profit | 2 | 2 | 1 | 2008 |
| EMS S/A | For profit | 1 | 1 | 1 | 2022 |
| Perrigo | For profit | 1 | 1 | 1 | 2008 |
Marketing (8)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Bayer | For profit | NDA2 | Dec 21, 1995 |
| Padagis Us | For profit | MKTG | May 18, 2012 |
| Padagis Us | For profit | MKTG | Feb 7, 1997 |
| Padagis Us | For profit | NDA2 | Feb 7, 1997 |
| Perrigo | For profit | NDA2 | Feb 7, 1997 |
| Perrigo | For profit | MKTG | May 18, 2012 |
| Roche | For profit | NDA2 | — |
| Syntex | For profit | NDA | — |