miconazole
Trade name: monistat
Approved
Jan 8, 1974
Miconazole is a synthetic imidazole derivative, a topical antifungal agent for use in the local treatment of vaginal, and skin and nail infections due to yeasts and dermatophytes. It is particularly active against Candida spp., Trichophyton spp., Epidermophyton spp., Microsporum spp. and Pityrosporon orbiculare (Malassezia furfur), but also possesses some activity against Gram-positive bacteria. It binds to the heme moiety of the fungal cytochrome P-450 dependent enzyme lanosterol 14-alpha-demethlyase. Inhibits 14-alpha-demethlyase, blocks formation of ergosterol and leads to the buildup of toxic methylated 14-a-sterols. Miconazole also affects the synthesis of triglycerides and fatty acids and inhibits oxidative and peroxidative enzymes, increasing the amount of active oxygen species within the cell. — NCATS
Clinical trial activity
28 trials · 39 clinical orgs · 15 marketing orgs
Earliest trial started Feb 1, 2000 (NCT00004575)
Timeline
1970s
- Jan 8, 1974
Earliest FDA Approval
- Jan 8, 1974
Insight Pharmaceuticals — NDA Secondary Org
- Jan 30, 1974
Medtech Products — NDA Secondary Org
- Oct 4, 1978
Johnson and Johnson — First NDA Organization
- Oct 4, 1978
Johnson and Johnson — NDA Secondary Org
- Oct 4, 1978
Johnson and Johnson — NDA Organization
1980s
- Oct 27, 1989
Personal Products — NDA Secondary Org
1990s
- Nov 19, 1993
P&L Development — Marketing Organization
- Jan 4, 1995
Teva — Marketing Organization
- Feb 22, 1996
Cosette — Marketing Organization
- Feb 22, 1996
ACP Nimble — Marketing Organization
- Mar 29, 1996
Actavis — Marketing Organization
- Mar 20, 1997
Perrigo — Marketing Organization
- Apr 30, 1997
G & W Laboratories Inc. — Marketing Organization
2000s
- Jan 1, 2000
Earliest Phase 1 Sponsor(trial)
- Mar 2, 2005
Taro Pharmaceuticals — Marketing Organization
- Jan 1, 2006
Earliest Phase 3 Sponsor(trial)
- Feb 16, 2006
Mylan — Marketing Organization
- Feb 16, 2006
Mylan — NDA Secondary Org
2010s
- Apr 16, 2010
Galt Pharmaceuticals — Marketing Organization
- Apr 16, 2010
Midatech Pharma — NDA Secondary Org
- Apr 16, 2010
Midatech Pharma — Marketing Organization
- Apr 16, 2010
Galt Pharmaceuticals — NDA Secondary Org
- Jan 1, 2011
Earliest Phase 2 Sponsor(trial)
Indications
Approved for
Studied for
- Candidiasis · Phase 4
- Candidiasis, Oral · Phase 3
- Candidiasis, Vulvovaginal · Phase 4
- Diaper Rash · Phase 4
- Drug-Related Side Effects and Adverse Reactions · Phase 2
- Endometriosis · Phase 1
- Health · Phase 4
- Healthy Volunteers · Phase 1
- HIV · Phase 1
- HIV Infections · Phase 3
- Intertrigo · Early Phase 1
- Melanosis · Phase 4
- Mucositis · Phase 2
- Onychomycosis · Phase 2
- Otomycosis · Phase 3
- Stomatitis, Denture · Phase 3
- Tinea Cruris · Phase 2
- Trichomonas Infections · Phase 2
- Trichomonas Vaginitis · Phase 2
- Vaginitis · Phase 3
- Vaginosis, Bacterial · Phase 2
Mechanism of action
- Cytochrome P450 51INHIBITOR
ERG11 inhibitor
Combination products
vusion
with petrolatum, white, zinc oxide
Approval history
- approvedJan 8, 1974
Chemistry & pharmacology
SMILES
Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)c(Cl)c1- Mol. weight
- 416.13 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral, Topical
- Availability
- Over the Counter
Oral
No
Parenteral
Yes
Topical
Yes
Sources
- ChEMBLCHEMBL91 ↗
- WikipediaMiconazole ↗
- NCATS7NNO0D7S5M ↗
- ChEMBLCHEMBL1559 ↗
Also known as
- 1-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1h-imidazole
- 1-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1h-imidazole
- 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
- 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
- acorvio
- conofite
- conofite
- daktarin aktiv
- daktarin iv
- daktarin iv
- dermazole
- dermonistat
- dermonistat
- dumicoat
- femeron
- gyno-daktarin
- gyno-daktarin
- loramyc
- micatin
- micatin
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole
- miconazole 3
- miconazole 3
- miconazole 3 combination pack
- miconazole 3 combination pack
- miconazole 7
- miconazole 7
- miconazole 7 combination pack
- miconazole 7 combination pack
- miconazole lauriad
- miconazole nitrate
- miconazole nitrate
- miconazole nitrate
- miconazole nitrate
- miconazole nitrate
- miconazole nitrate combination pack
- miconazole nitrate combination pack
- miconazole oil
- monistat
- monistat
- monistat
- monistat 1 combination pack
- monistat 1 combination pack
- monistat 3
- monistat 3
- monistat-3
- monistat-3
- monistat 3 combination pack
- monistat 3 combination pack
- monistat-3 combination pack
- monistat-3 combination pack
- monistat 3 combination pack (prefilled)
- monistat 3 combination pack (prefilled)
- monistat 5
- monistat 5
- monistat 7
- monistat 7
- monistat 7 combination pack
- monistat 7 combination pack
- monistat-derm
- monistat-derm
- monistat iv (tn)
- monistat iv (tn)
- m-zole 3 combination pack
- m-zole 3 combination pack
- m-zole 7 dual pack
- m-zole 7 dual pack
- oravig
- oravig
- r-14889
- r-14889
- vusion
- vusion
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07311759 | Phase 3 | Aug 17, 2024 | Cairo University |
| NCT06214273 | Phase 2 | Apr 30, 2024 | Cairo University |
| NCT05660382 | Phase 3 | May 31, 2023 | Hill Dermaceuticals, Inc. |
| NCT04813822 | Phase 2 | Sep 30, 2021 | Aesculap AG |
| NCT04432376 | Phase 2/Phase 3 (Phase 3) | Jun 30, 2020 | Abond CRO Inc., Advanced ENT and Allergy, Carolina ENT, DaVinci Research LLC, DelRicht Research, Hill Dermaceuticals, Inc., OnSite Clinical Solutions, University of California, San Diego, University of Missouri |
| NCT04341402 | Phase 2 | May 1, 2020 | Bay Area Medical |
| NCT04308161 | Phase 2 | Nov 2, 2019 | Alexandria University |
| NCT03949751 | N/A | Oct 1, 2019 | Balgrist Universitaets |
| NCT04317183 | Phase 2 | May 15, 2019 | Alexandria University |
| NCT04442633 | N/A | Apr 1, 2019 | Alexandria University |
| NCT03833570 | Phase 2 | Jan 12, 2018 | Alexandria University |
| NCT03130738 | Phase 2 | Apr 20, 2017 | Hill Dermaceuticals, Inc. |
| NCT02818803 | Phase 3 | Jan 1, 2016 | Centro Universitário, Government of Brazil, University of Sao Paulo |
| NCT02515656 | Phase 3 | Sep 1, 2015 | Fournier Labs, International Clinical Trials Association, Laboratoire Innotech International, Venn Life Sciences |
| NCT02545452 | Phase 1 | Sep 1, 2015 | Bayer |
| NCT02185456 | Early Phase 1 (Phase 1) | Sep 1, 2014 | National Institute of Allergy and Infectious Diseases (NIAID), Wayne State University |
| NCT03359070 | Phase 2 | Jan 29, 2014 | Biolab Sanus Farmaceutica, Galeno Desenvolvimento de Pesquisas |
| NCT01731574 | Phase 1 | Dec 1, 2012 | International Partnership for Microbicides, Inc. |
| NCT01361048 | Phase 2 | Dec 1, 2011 | Embil Pharmaceutical Co. Ltd, University of Alabama, Birmingham |
| NCT01661556 | Phase 4 | Oct 1, 2011 | Universidad Autonoma de San Luis Potosi |
Organizations
Research & Development (39)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Alexandria University | Academic/Hospital | 4 | 4 | 2 | 2018 |
| Hill Dermaceuticals, Inc. | For profit | 3 | 3 | 2 | 2017 |
| Cairo University | Academic/Hospital | 2 | 2 | 2 | 2024 |
| Johnson and Johnson | For profit | 2 | 1 | 1 | 2004 |
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 2 | 1 | 2 | 2011 |
| Abond CRO Inc. | For profit | 1 | 0 | 1 | 2020 |
| Advanced ENT and Allergy | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Aesculap AG | For profit | 1 | 1 | 1 | 2021 |
| Balgrist Universitaets | Academic/Hospital | 1 | 1 | 1 | 2019 |
| Bay Area Medical | Academic/Hospital | 1 | 1 | 1 | 2020 |
| Bayer | For profit | 1 | 1 | 1 | 2015 |
| Biolab Sanus Farmaceutica | For profit | 1 | 0 | 1 | 2014 |
| Carolina ENT | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Centro Universitário | Academic/Hospital | 1 | 0 | 1 | 2016 |
| DaVinci Research LLC | For profit | 1 | 0 | 1 | 2020 |
| DelRicht Research | For profit | 1 | 0 | 1 | 2020 |
| Embil Pharmaceutical Co. Ltd | For profit | 1 | 0 | 1 | 2011 |
| Fournier Labs | For profit | 1 | 0 | 1 | 2015 |
| Galeno Desenvolvimento de Pesquisas | Academic/Hospital | 1 | 1 | 1 | 2014 |
| GlaxoSmithKline | For profit | 1 | 0 | 1 | 2007 |
Marketing (26)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ACP Nimble | For profit | MKTG | Feb 22, 1996 |
| Actavis | For profit | MKTG | Mar 29, 1996 |
| Actavis | For profit | SYN | Nov 19, 1993 |
| Cosette | For profit | MKTG | Feb 22, 1996 |
| G & W Laboratories Inc. | For profit | MKTG | Apr 30, 1997 |
| G & W Laboratories Inc. | For profit | SYN | Feb 22, 1996 |
| Galt Pharmaceuticals | For profit | MKTG | Apr 16, 2010 |
| Galt Pharmaceuticals | For profit | NDA2 | Apr 16, 2010 |
| Insight Pharmaceuticals | For profit | NDA2 | Jan 8, 1974 |
| Johnson and Johnson | For profit | NDA2 | Oct 4, 1978 |
| Johnson and Johnson | For profit | NDA | Oct 4, 1978 |
| Medtech Products | For profit | NDA2 | Jan 30, 1974 |
| Midatech Pharma | For profit | NDA2 | Apr 16, 2010 |
| Midatech Pharma | For profit | MKTG | Apr 16, 2010 |
| Mylan | For profit | MKTG | Feb 16, 2006 |
| Mylan | For profit | SYN | Feb 16, 2006 |
| Mylan | For profit | NDA2 | Feb 16, 2006 |
| P&L Development | For profit | MKTG | Nov 19, 1993 |
| Perrigo | For profit | MKTG | Mar 20, 1997 |
| Perrigo | For profit | SYN | Jan 15, 2010 |
| Perrigo | For profit | SYN | Apr 20, 1999 |
| Personal Products | For profit | NDA2 | Oct 27, 1989 |
| Taro Pharmaceuticals | For profit | MKTG | Mar 2, 2005 |
| Taro Pharmaceuticals | For profit | SYN | Jan 13, 1997 |
| Teva | For profit | MKTG | Jan 4, 1995 |
| Teva | For profit | SYN | Oct 30, 1992 |