nortriptyline
Trade name: aventyl
Approved
Nov 6, 1964
Nortriptyline is a second-generation tricyclic antidepressant (TCA) marketed as the hydrochloride salt under the trade names Sensoval, Aventyl, Pamelor, Norpress, Allegron, Noritren and Nortrilen. Nortriptyline is used in the treatment of depression and childhood nocturnal enuresis. Its off-label uses include treatment of postherpetic neuralgia, angioedema and smoking Cessation, and attention deficit hyperactivity disorder in some neurological disorders. It is believed that nortriptyline either inhibits the reuptake of the neurotransmitter serotonin at the neuronal membrane or acts at beta-adrenergic receptors. Nortriptyline is US FDA-approved for the treatment of major depression. In the United Kingdom, it may also be used for treating nocturnal enuresis, with courses of treatment lasting no more than three months. The most common side effects include dry mouth, sedation, constipation, and increased appetite, mild blurred vision, tinnitus, occasionally hypomania or mania. An occasional side effect is a rapid or irregular heartbeat. Alcohol may exacerbate some of its side effects. However, fewer and milder side effects occur with nortriptyline than tertiary tricyclic antidepressants such as imipramine and amitriptyline. For this reason, nortriptyline is preferred to other tricyclic antidepressants, particularly with older adults, which also improves compliance. — NCATS
Clinical trial activity
46 trials · 42 clinical orgs · 14 marketing orgs
Earliest trial started Mar 1, 1989 (NCT00000377)
Timeline
1960s
1970s
- Aug 1, 1977
Specgx Llc — NDA Secondary Org
1990s
- Mar 30, 1992
Mayne Pharma — Marketing Organization
- Mar 30, 1992
Dr. Reddy's Laboratories — Marketing Organization
- Dec 31, 1992
Ani Pharmaceuticals — Marketing Organization
- Jul 26, 1993
Rising Pharmaceuticals — Marketing Organization
- Jul 26, 1993
Mylan — Marketing Organization
- Jan 1, 1995
Earliest Phase 3 Sponsor(trial)
- Mar 27, 1995
Teva — Marketing Organization
- Jun 30, 1997
Aurobindo Pharma — Marketing Organization
- Jan 1, 1998
Earliest Phase 2 Sponsor(trial)
2000s
- Aug 23, 2000
Pharmaceutical Associates — Marketing Organization
- Jan 1, 2006
Earliest Phase 1 Sponsor(trial)
- Jun 20, 2006
Taro Pharmaceuticals — Marketing Organization
2020s
- Feb 24, 2021
Zydus Discovery DMCC — Marketing Organization
- Aug 15, 2023
Rubicon Research — Marketing Organization
Indications
Approved for
Studied for
- Anxiety Disorders · Phase 3
- Back Pain · Phase 2
- Bipolar Disorder · Phase 4
- Brain Concussion · Phase 4
- Carcinoma, Small Cell · Phase 1
- Cognitive Dysfunction · Phase 4
- Counseling · Phase 1/Phase 2
- Cystitis, Interstitial · Phase 2
- Dementia · Phase 4
- Depression · Phase 4
- Depressive Disorder, Treatment-Resistant · Phase 4
- Dermatitis, Atopic · Phase 1
- Dyspepsia · Phase 3
- Endometriosis · Phase 2
- Fatigue Syndrome, Chronic · Phase 2
- Fibromyalgia · Phase 2
- Gastroesophageal Reflux · Phase 3
- Headache · Phase 4
- Healthy Volunteers · Phase 1
- Herpes Zoster · Phase 3
- Irritable Bowel Syndrome · Phase 2
- Major Depressive Disorder · Phase 4
- Meniere Disease · Phase 4
- Migraine Disorders · Phase 4
- Pain · Phase 3
- Parkinson Disease · Phase 3
- Polyradiculoneuropathy · Phase 4
- Post-Concussion Syndrome · Phase 4
- Psoriasis · Phase 2
- Psychophysiologic Disorders · Phase 3
- Radiculopathy · Phase 2
- Schizophrenia · Phase 3
- Sciatica · Phase 2
- Smoking · Phase 2
- Stomach Diseases · Phase 3
- Temporomandibular Joint Disorders · Phase 2
- Tension-Type Headache · Phase 2
- Tinnitus · Phase 4
- Vulvodynia · Phase 2
Mechanism of action
- Norepinephrine transporterINHIBITOR
SLC6A2 inhibitor
- Serotonin transporterINHIBITOR
SLC6A4 inhibitor
Approval history
- approvedNov 6, 1964
Chemistry & pharmacology
SMILES
CNCCC=C1c2ccccc2CCc2ccccc21- Mol. weight
- 263.38 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL445 ↗
- WikipediaNortriptyline ↗
- NCATSBL03SY4LXB ↗
- ChEMBLCHEMBL1201156 ↗
Also known as
- 10,11-dihydro-n-methyl-5h-dibenzo[a,d]cycloheptene-delta(5,gamma)-propylamine
- 10,11-dihydro-n-methyl-5h-dibenzo[a,d]cycloheptene-delta(5,gamma)-propylamine
- 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n-methyl-1-propanamine
- 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n-methyl-1-propanamine
- 38489
- 38489
- allegron
- allegron
- ateben
- ateben
- avantyl
- avantyl
- aventyl
- aventyl
- aventyl
- aventyl hcl
- aventyl hcl
- crx-197
- demethylamitriptylin
- demethylamitriptyline
- demethylamitriptyline
- desitriptilina
- desmethylamitriptyline
- desmethylamitriptyline
- desmethylamitriptyline
- motipress
- motipress
- motipress
- motival
- motival
- motival
- noramitriptyline
- noritren
- noritren
- nortriptyline
- nortriptyline
- nortriptyline
- nortriptyline
- nortriptyline
- nortriptyline
- nortriptyline
- nortriptyline
- nortriptyline hcl
- nortriptyline hcl
- nortriptyline hcl
- nortriptyline hydrochloride
- nortriptyline hydrochloride
- nortriptyline hydrochloride
- nortriptyline hydrochloride
- nortryptyline
- nortryptyline
- nortryptyline
- nortryptyline
- nortryptyline
- nortryptyline
- pamelor
- pamelor
- psychostyl
- psychostyl
- psychostyl
- sensaval
- sensaval
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06799169 | Phase 4 | Mar 31, 2025 | University of California, Irvine |
| NCT05582837 | Phase 4 | Aug 1, 2022 | University of California, Irvine |
| NCT04226365 | Phase 4 | Feb 3, 2020 | Lancaster General Hospital |
| NCT03652870 | Phase 3 | Nov 1, 2019 | NHS Lothian, University Hospital Plymouth NHS Trust, University of London |
| NCT04404439 | Phase 4 | Sep 26, 2019 | University of California, Irvine |
| NCT05531591 | Phase 4 | Aug 1, 2019 | National Institute of Mental Health (NIMH), University of Toronto |
| NCT03844412 | Phase 2 | Jun 1, 2019 | Duke University, National Institutes of Health (NIH) |
| NCT03652571 | Phase 3 | Sep 1, 2018 | Maastricht University |
| NCT02960763 | Phase 4 | Feb 24, 2017 | Cancer Research Network, Washington University in St. Louis |
| NCT02881125 | Phase 1 | Nov 3, 2016 | National Cancer Institute (NCI), University of Washington |
| NCT02374567 | Phase 3 | Jan 1, 2015 | Gottfried Wilhelm Leibniz Universität Hannover |
| NCT02260388 | Phase 4 | Oct 1, 2014 | Cancer Research Network, University of Kansas |
| NCT02169830 | N/A | Jun 1, 2014 | St. Louis University |
| NCT01943435 | N/A | Oct 1, 2013 | Cancer Research Network, University of Pittsburgh |
| NCT01896349 | N/A | Apr 1, 2013 | Federal University of Rio Grande do Sul |
| NCT02237937 | Phase 4 | Sep 1, 2011 | HolsboerMaschmeyer NeuroChemie GmbH, Max Planck Institute |
| NCT01268709 | Phase 2 | Dec 30, 2010 | Qom University of Medical Sciences |
| NCT02901249 | Phase 4 | May 1, 2010 | Federal University of Rio Grande do Sul |
| NCT02918097 | Phase 4 | May 1, 2010 | Federal University of Rio Grande do Sul |
| NCT01065649 | Phase 3 | Jan 1, 2010 | Conselho Nacional de Desenvolvimento Científico e Tecnológico, Universidade de Passo Fundo |
Organizations
Research & Development (42)
Marketing (20)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Ani Pharmaceuticals | For profit | MKTG | Dec 31, 1992 |
| Ani Pharmaceuticals | For profit | SYN | Dec 31, 1992 |
| Aurobindo Pharma | For profit | MKTG | Jun 30, 1997 |
| Aurobindo Pharma | For profit | SYN | Jun 30, 1997 |
| Dr. Reddy's Laboratories | For profit | MKTG | Mar 30, 1992 |
| Eli Lilly | For profit | NDA2 | Nov 6, 1964 |
| Mayne Pharma | For profit | MKTG | Mar 30, 1992 |
| Mylan | For profit | MKTG | Jul 26, 1993 |
| Pharmaceutical Associates | For profit | MKTG | Aug 23, 2000 |
| Ranbaxy | For profit | NDA2 | Nov 6, 1964 |
| Ranbaxy | For profit | NDA | Nov 6, 1964 |
| Rising Pharmaceuticals | For profit | MKTG | Jul 26, 1993 |
| Rubicon Research | For profit | MKTG | Aug 15, 2023 |
| Rubicon Research | For profit | SYN | Aug 15, 2023 |
| Specgx Llc | For profit | NDA2 | Aug 1, 1977 |
| Taro Pharmaceuticals | For profit | MKTG | Jun 20, 2006 |
| Taro Pharmaceuticals | For profit | SYN | May 8, 2000 |
| Teva | For profit | MKTG | Mar 27, 1995 |
| Zydus Discovery DMCC | For profit | SYN | Feb 24, 2021 |
| Zydus Discovery DMCC | For profit | MKTG | Feb 24, 2021 |