ciclopirox
Trade name: loprox
Approved
Dec 30, 1982
Ciclopirox is an antifungal medication indicated for the treatment of seborrheic dermatitis (Loprox trade name) and onychomycosis of fingernails and toenails due to Trichophyton rubrum (Penlac trade name). The drug exerts its action by chelating Fe3+ and Al3+, resulting in the inhibition of the metal-dependent enzymes that are responsible for the degradation of peroxides within the fungal cell. — NCATS
Clinical trial activity
17 trials · 20 clinical orgs · 33 marketing orgs
Earliest trial started Mar 1, 2002 (NCT01419847)
Timeline
1980s
- Dec 30, 1982
Medimetriks — Earliest FDA Approval
- Dec 30, 1982
Medimetriks — NDA Organization
- Dec 30, 1982
Medimetriks — NDA Secondary Org
1990s
- Jul 21, 1997
County Line — NDA Secondary Org
- Jul 21, 1997
Alvogen — Marketing Organization
- Jul 21, 1997
Alvogen — NDA Secondary Org
- Dec 17, 1999
Bausch Health Companies — NDA Secondary Org
2000s
- Jan 1, 2003
- Feb 28, 2003
Medicis — NDA Secondary Org
- Feb 28, 2003
Bausch Health Companies — Marketing Organization
- Aug 6, 2004
Fougera — Marketing Organization
- Mar 3, 2006
Perrigo — Marketing Organization
- Mar 3, 2006
Padagis Us — Marketing Organization
- Sep 18, 2007
Chartwell Pharmaceuticals — Marketing Organization
- Sep 18, 2007
Encube Ethicals Pvt. Ltd. — Marketing Organization
- Sep 18, 2007
Cosette — Marketing Organization
- Sep 18, 2007
Rising Pharmaceuticals — Marketing Organization
- Sep 18, 2007
ACP Nimble — Marketing Organization
- Sep 18, 2007
Actavis — Marketing Organization
- Sep 18, 2007
Apotex — Marketing Organization
- Sep 18, 2007
G & W Laboratories Inc. — Marketing Organization
- Sep 18, 2007
Hi Tech Pharmaceuticals — Marketing Organization
- Sep 18, 2007
Ingenus Pharmaceuticals — Marketing Organization
- Sep 18, 2007
Mylan — Marketing Organization
- Sep 18, 2007
Taro Pharmaceuticals — Marketing Organization
- Sep 18, 2007
Teva — Marketing Organization
- Sep 18, 2007
Tolmar Inc. — Marketing Organization
- Sep 18, 2007
Acella Pharmaceuticals — Marketing Organization
- Sep 18, 2007
ANDA Repository — Marketing Organization
- Sep 18, 2007
Novast Labs — Marketing Organization
- Sep 18, 2007
Hikma — Marketing Organization
- Jan 1, 2009
Earliest Phase 1 Sponsor(trial)
- Jan 7, 2009
Paddock Laboratories — Marketing Organization
2010s
- Feb 17, 2010
Akorn, Inc. — Marketing Organization
- Feb 17, 2010
Epic Pharma Llc — Marketing Organization
- Feb 23, 2011
Sun Pharmaceuticals — Marketing Organization
- Feb 29, 2012
Glenmark Pharmaceuticals — Marketing Organization
- Jan 1, 2016
Earliest Phase 2 Sponsor(trial)
- Apr 5, 2018
Pharmaceutical Associates — Marketing Organization
- Apr 5, 2018
Teligent Pharmaceuticals — Marketing Organization
Indications
Studied for
- Dermatitis, Seborrheic · Phase 4
- Dermatomycoses · Phase 4
- Foot Dermatoses · Phase 4
- Hematologic Neoplasms · Phase 1
- Hodgkin Disease · Phase 1
- Leukemia, Lymphocytic, Chronic, B-Cell · Phase 1
- Leukemia, Myelogenous, Chronic, BCR-ABL Positive · Phase 1
- Leukemia, Myeloid, Acute · Phase 1
- Myelodysplastic Syndromes · Phase 1
- Pharmacokinetics · Phase 1
- Precursor Cell Lymphoblastic Leukemia-Lymphoma · Phase 1
- Quality of Life · Phase 4
- Tinea Pedis · Phase 3
Mechanism of action
- AluminiumCHELATING AGENT
Aluminium chelating agent
Trivalent metal cations chelating agent; inhibition of the metal-dependent enzymes that are responsible for the degradation of peroxides within the fungal cell
- IronCHELATING AGENT
Iron chelating agent
Trivalent metal cations chelating agent; inhibition of the metal-dependent enzymes that are responsible for the degradation of peroxides within the fungal cell
Approval history
- approvedDec 30, 1982
Chemistry & pharmacology
SMILES
Cc1cc(C2CCCCC2)n(O)c(=O)c1- Mol. weight
- 207.27 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- Yes
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Topical
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
Yes
Sources
- ChEMBLCHEMBL1413 ↗
- WikipediaCiclopirox ↗
- NCATS19W019ZDRJ ↗
- ChEMBLCHEMBL242580 ↗
Also known as
- 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridinone
- 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridinone
- 6-cyclohexyl-1-hydroxy-4-methyl-2(1h)-pyridone ethanolamine salt
- batrafen
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox
- ciclopirox ethanolamine
- ciclopiroxolamine
- ciclopirox olamine
- ciclopirox olamine
- ciclopirox olamine
- ciclopirox olamine
- ciclopirox olamine
- ciclopiroxum
- ciclopiroxum
- cicloprox
- cyclopirox
- cyclopyroxolamine
- dafnegin-csc
- hoe 296
- hoe-296
- hoe-296
- hoe-296
- hoe-296b
- hoe-296b
- loprox
- loprox
- loprox
- loprox
- mycoster
- mycoster
- penlac
- penlac
- penlac
- penlac
- penlac
- rv4104a
- rv4104a
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05809297 | Phase 4 | Sep 1, 2023 | Universidad Complutense de Madrid |
| NCT05647343 | Phase 1 | Jan 31, 2023 | Atlas Molecular Pharma |
| NCT02961634 | Phase 3 | Apr 1, 2017 | MIP Brasil Indústria e Comércio de Produtos Farmacêuticos LTDA |
| NCT02644551 | Phase 2 | Nov 1, 2016 | 9305-9954 Quebec Inc |
| NCT02866032 | Phase 3 | Sep 1, 2016 | Moberg Pharma AB |
| NCT02679911 | Phase 4 | Sep 1, 2015 | Galderma |
| NCT02004860 | Phase 3 | Jan 1, 2014 | Rouen Normandy University |
| NCT01139749 | Phase 4 | Oct 1, 2011 | University of Sao Paulo |
| NCT00990587 | Phase 1 | Oct 1, 2009 | The Leukemia and Lymphoma Society, University of Toronto |
| NCT01014637 | Phase 4 | Aug 1, 2009 | Hopital Purpan, Pierre Fabre, QuantaBio |
| NCT01646580 | Phase 4 | Oct 1, 2008 | Ferrer Internacional S.A., Universidad de Cordoba |
| NCT00808366 | N/A | Oct 1, 2008 | Pierre Fabre |
| NCT00382330 | N/A | Sep 27, 2006 | University of Medicine and Dentistry of New Jersey |
| NCT00127868 | N/A | Mar 1, 2005 | Chen, Catherine, M.D., Eastern Virginia Medical School |
| NCT00804193 | N/A | Jun 1, 2004 | Perrigo |
| NCT00802672 | Phase 3 | Dec 1, 2003 | Perrigo |
| NCT01419847 | Phase 4 | Mar 1, 2002 | University of California, San Diego |
Organizations
Research & Development (20)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Perrigo | For profit | 2 | 2 | 2 | 2003 |
| Pierre Fabre | For profit | 2 | 2 | 2 | 2008 |
| 9305-9954 Quebec Inc | For profit | 1 | 1 | 1 | 2016 |
| Atlas Molecular Pharma | For profit | 1 | 1 | 1 | 2023 |
| Chen, Catherine, M.D. | Academic/Hospital | 1 | 1 | 1 | 2005 |
| Eastern Virginia Medical School | Academic/Hospital | 1 | 0 | 1 | 2005 |
| Ferrer Internacional S.A. | For profit | 1 | 1 | 1 | 2008 |
| Galderma | For profit | 1 | 1 | 1 | 2015 |
| Hopital Purpan | Academic/Hospital | 1 | 0 | 1 | 2009 |
| MIP Brasil Indústria e Comércio de Produtos Farmacêuticos LTDA | For profit | 1 | 1 | 1 | 2017 |
| Moberg Pharma AB | For profit | 1 | 1 | 1 | 2016 |
| QuantaBio | For profit | 1 | 0 | 1 | 2009 |
| Rouen Normandy University | Academic/Hospital | 1 | 1 | 1 | 2014 |
| The Leukemia and Lymphoma Society | Academic/Hospital | 1 | 0 | 1 | 2009 |
| Universidad Complutense de Madrid | Academic/Hospital | 1 | 1 | 1 | 2023 |
| Universidad de Cordoba | Academic/Hospital | 1 | 0 | 1 | 2008 |
| University of California, San Diego | Academic/Hospital | 1 | 1 | 1 | 2002 |
| University of Medicine and Dentistry of New Jersey | Academic/Hospital | 1 | 1 | 1 | 2006 |
| University of Sao Paulo | Academic/Hospital | 1 | 1 | 1 | 2011 |
| University of Toronto | Academic/Hospital | 1 | 1 | 1 | 2009 |
Marketing (44)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ACP Nimble | For profit | MKTG | Sep 18, 2007 |
| ANDA Repository | For profit | MKTG | Sep 18, 2007 |
| Acella Pharmaceuticals | For profit | MKTG | Sep 18, 2007 |
| Actavis | For profit | MKTG | Sep 18, 2007 |
| Akorn, Inc. | For profit | MKTG | Feb 17, 2010 |
| Alvogen | For profit | MKTG | Jul 21, 1997 |
| Alvogen | For profit | NDA2 | Jul 21, 1997 |
| Apotex | For profit | MKTG | Sep 18, 2007 |
| Bausch Health Companies | For profit | NDA2 | Dec 17, 1999 |
| Bausch Health Companies | For profit | MKTG | Feb 28, 2003 |
| Chartwell Pharmaceuticals | For profit | MKTG | Sep 18, 2007 |
| Cosette | For profit | MKTG | Sep 18, 2007 |
| County Line | For profit | NDA2 | Jul 21, 1997 |
| Encube Ethicals Pvt. Ltd. | For profit | MKTG | Sep 18, 2007 |
| Epic Pharma Llc | For profit | MKTG | Feb 17, 2010 |
| Fougera | For profit | MKTG | Aug 6, 2004 |
| G & W Laboratories Inc. | For profit | MKTG | Sep 18, 2007 |
| G & W Laboratories Inc. | For profit | SYN | Dec 20, 2010 |
| Glenmark Pharmaceuticals | For profit | MKTG | Feb 29, 2012 |
| Glenmark Pharmaceuticals | For profit | SYN | Nov 10, 2009 |
| Glenmark Pharmaceuticals | For profit | SYN | Feb 29, 2012 |
| Hi Tech Pharmaceuticals | For profit | MKTG | Sep 18, 2007 |
| Hikma | For profit | MKTG | Sep 18, 2007 |
| Ingenus Pharmaceuticals | For profit | MKTG | Sep 18, 2007 |
| Medicis | For profit | NDA2 | Feb 28, 2003 |
| Medimetriks | For profit | NDA | Dec 30, 1982 |
| Medimetriks | For profit | NDA2 | Dec 30, 1982 |
| Mylan | For profit | MKTG | Sep 18, 2007 |
| Novast Labs | For profit | MKTG | Sep 18, 2007 |
| Padagis Us | For profit | MKTG | Mar 3, 2006 |
| Padagis Us | For profit | MKTG | Sep 18, 2007 |
| Paddock Laboratories | For profit | MKTG | Jan 7, 2009 |
| Perrigo | For profit | SYN | Feb 16, 2010 |
| Perrigo | For profit | MKTG | Mar 3, 2006 |
| Perrigo | For profit | SYN | Mar 3, 2006 |
| Pharmaceutical Associates | For profit | MKTG | Apr 5, 2018 |
| Rising Pharmaceuticals | For profit | MKTG | Sep 18, 2007 |
| Sun Pharmaceuticals | For profit | MKTG | Feb 23, 2011 |
| Taro Pharmaceuticals | For profit | SYN | Apr 12, 2005 |
| Taro Pharmaceuticals | For profit | MKTG | Sep 18, 2007 |
| Teligent Pharmaceuticals | For profit | SYN | Apr 5, 2018 |
| Teligent Pharmaceuticals | For profit | MKTG | Apr 5, 2018 |
| Teva | For profit | MKTG | Sep 18, 2007 |
| Tolmar Inc. | For profit | MKTG | Sep 18, 2007 |