levomilnacipran
Trade name: fetzima
Approved
Jul 25, 2013
Levomilnacipran (1S, 2R/F2695) is an enantiomer of milnacipran, a serotonin/norepinephrine (5-HT/NE) reuptake inhibitor. Levomilnacipran is pharmacologically more active as compared with racemic mixture and dextromilnacipran (1R, 2S/F2696). The safety of the drug is also higher than the safety of a racemate, resulting in a beneficial impact on the therapeutic effect. Pierre Fabre and Forest Laboratories are developing levomilnacipran extended release (ER) [FETZIMA™], an enantiomer of milnacipran, for the treatment of major depressive disorder (MDD). In addition, Pierre Fabre (the originator of the compound) is developing the drug to improve recovery in patients with ischaemic stroke. — NCATS
Clinical trial activity
13 trials · 8 clinical orgs · 9 marketing orgs
Earliest trial started Sep 1, 2009 (NCT00969150)
Timeline
2000s
- Jan 1, 2009
Forest Laboratories — Earliest Phase 3 Sponsor(trial)
2010s
- Jan 1, 2011
Forest Laboratories — Earliest Phase 2 Sponsor(trial)
- Jul 25, 2013
Forest Laboratories — Earliest FDA Approval
- Jul 25, 2013
Allergan — NDA Secondary Org
- Jul 25, 2013
Allergan — Marketing Organization
- Jul 25, 2013
Forest Laboratories — NDA Organization
- Jul 25, 2013
AbbVie — Marketing Organization
- Jul 25, 2013
AbbVie — NDA Secondary Org
- Feb 4, 2019
Amneal Pharmaceuticals — Marketing Organization
2020s
- Jun 1, 2020
MSN Laboratories — Marketing Organization
- Nov 5, 2020
Hikma — Marketing Organization
- Aug 17, 2022
Prinston Inc — Marketing Organization
- Jan 6, 2023
Aurobindo Pharma — Marketing Organization
- Jan 12, 2023
Zydus Discovery DMCC — Marketing Organization
Indications
Approved for
Mechanism of action
- Norepinephrine transporterINHIBITOR
SLC6A2 inhibitor
- Serotonin transporterINHIBITOR
SLC6A4 inhibitor
Approval history
- approvedJul 25, 2013
Chemistry & pharmacology
SMILES
CCN(CC)C(=O)[C@@]1(c2ccccc2)C[C@H]1CN- Mol. weight
- 246.35 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL99946 ↗
- WikipediaLevomilnacipran ↗
- NCATSUGM0326TXX ↗
- ChEMBLCHEMBL2105732 ↗
Also known as
- (1s,2r)-milnacipran
- (1s,2r)-milnacipran
- f2695
- f2695
- f-2695
- f-2695
- fetzima
- fetzima
- fetzima
- fetzima
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran
- levomilnacipran hcl
- levomilnacipran hcl
- levomilnacipran hcl
- levomilnacipran hydrochloride
- levomilnacipran hydrochloride
- levomilnacipran hydrochloride
- levomilnacipran hydrochloride
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07253207 | Phase 3 | Oct 17, 2024 | Zhejiang Huahai Pharmaceutical Co., Ltd. |
| NCT03569475 | Phase 3 | Jul 6, 2018 | Allergan |
| NCT03249311 | Phase 4 | Mar 2, 2018 | Allergan, University of Ottawa |
| NCT02720198 | Phase 3 | Jan 23, 2017 | Duke University, Forest Laboratories, Institute for Advanced Medical Research, Alpharetta, GA |
| NCT02466958 | Phase 3 | Jun 1, 2016 | University of California, Los Angeles |
| NCT02431806 | Phase 3 | Jun 23, 2015 | Allergan, Forest Laboratories |
| NCT02265367 | N/A | Jan 1, 2015 | University of Minnesota |
| NCT02288325 | Phase 4 | Nov 1, 2014 | Allergan, Forest Laboratories |
| NCT01377194 | Phase 3 | Jun 1, 2011 | Forest Laboratories |
| NCT01254305 | Phase 2 | Apr 1, 2011 | Forest Laboratories |
| NCT01034462 | Phase 3 | Dec 1, 2009 | Forest Laboratories |
| NCT00969150 | Phase 3 | Sep 1, 2009 | Forest Laboratories |
| NCT00969709 | Phase 3 | Sep 1, 2009 | Forest Laboratories |
Organizations
Research & Development (8)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Forest Laboratories | For profit | 8 | 7 | 3 | 2009 |
| Allergan | For profit | 4 | 1 | 2 | 2014 |
| Duke University | Academic/Hospital | 1 | 1 | 1 | 2017 |
| Institute for Advanced Medical Research, Alpharetta, GA | Academic/Hospital | 1 | 0 | 1 | 2017 |
| University of California, Los Angeles | Academic/Hospital | 1 | 1 | 1 | 2016 |
| University of Minnesota | Academic/Hospital | 1 | 1 | 1 | 2015 |
| University of Ottawa | Academic/Hospital | 1 | 1 | 1 | 2018 |
| Zhejiang Huahai Pharmaceutical Co., Ltd. | For profit | 1 | 1 | 1 | 2024 |
Marketing (13)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| AbbVie | For profit | MKTG | Jul 25, 2013 |
| AbbVie | For profit | NDA2 | Jul 25, 2013 |
| Allergan | For profit | NDA2 | Jul 25, 2013 |
| Allergan | For profit | MKTG | Jul 25, 2013 |
| Amneal Pharmaceuticals | For profit | MKTG | Feb 4, 2019 |
| Aurobindo Pharma | For profit | MKTG | Jan 6, 2023 |
| Forest Laboratories | For profit | NDA | Jul 25, 2013 |
| Hikma | For profit | MKTG | Nov 5, 2020 |
| Hikma | For profit | SYN | Nov 5, 2020 |
| MSN Laboratories | For profit | MKTG | Jun 1, 2020 |
| Prinston Inc | For profit | MKTG | Aug 17, 2022 |
| Prinston Inc | For profit | SYN | Mar 20, 2023 |
| Zydus Discovery DMCC | For profit | MKTG | Jan 12, 2023 |