nortriptyline

Trade name: aventyl

Small moleculeapproved

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

Phase 1
4
Phase 2
16
Phase 3
6
Phase 4
16

Earliest trial started Mar 1, 1989 (NCT00000377)

Timeline

1960s

  1. Nov 6, 1964

    Ranbaxy — Earliest FDA Approval

  2. Nov 6, 1964

    Ranbaxy — NDA Secondary Org

  3. Nov 6, 1964

    Eli Lilly — NDA Secondary Org

  4. Nov 6, 1964

    Ranbaxy — NDA Organization

1970s

  1. Aug 1, 1977

    Specgx Llc — NDA Secondary Org

1990s

  1. Mar 30, 1992

    Mayne Pharma — Marketing Organization

  2. Mar 30, 1992

    Dr. Reddy's Laboratories — Marketing Organization

  3. Dec 31, 1992

    Ani Pharmaceuticals — Marketing Organization

  4. Jul 26, 1993

    Rising Pharmaceuticals — Marketing Organization

  5. Jul 26, 1993

    Mylan — Marketing Organization

  6. Jan 1, 1995

    Earliest Phase 3 Sponsor(trial)

  7. Mar 27, 1995

    Teva — Marketing Organization

  8. Jun 30, 1997

    Aurobindo Pharma — Marketing Organization

  9. Jan 1, 1998

    Earliest Phase 2 Sponsor(trial)

2000s

  1. Aug 23, 2000

    Pharmaceutical Associates — Marketing Organization

  2. Jan 1, 2006

    Earliest Phase 1 Sponsor(trial)

  3. Jun 20, 2006

    Taro Pharmaceuticals — Marketing Organization

2020s

  1. Feb 24, 2021

    Zydus Discovery DMCC — Marketing Organization

  2. Aug 15, 2023

    Rubicon Research — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedNov 6, 1964

Chemistry & pharmacology

Loading structure…

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

Black box warning

Sources

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 IDPhaseStart dateSponsor(s)
NCT06799169Phase 4Mar 31, 2025University of California, Irvine
NCT05582837Phase 4Aug 1, 2022University of California, Irvine
NCT04226365Phase 4Feb 3, 2020Lancaster General Hospital
NCT03652870Phase 3Nov 1, 2019NHS Lothian, University Hospital Plymouth NHS Trust, University of London
NCT04404439Phase 4Sep 26, 2019University of California, Irvine
NCT05531591Phase 4Aug 1, 2019National Institute of Mental Health (NIMH), University of Toronto
NCT03844412Phase 2Jun 1, 2019Duke University, National Institutes of Health (NIH)
NCT03652571Phase 3Sep 1, 2018Maastricht University
NCT02960763Phase 4Feb 24, 2017Cancer Research Network, Washington University in St. Louis
NCT02881125Phase 1Nov 3, 2016National Cancer Institute (NCI), University of Washington
NCT02374567Phase 3Jan 1, 2015Gottfried Wilhelm Leibniz Universität Hannover
NCT02260388Phase 4Oct 1, 2014Cancer Research Network, University of Kansas
NCT02169830N/AJun 1, 2014St. Louis University
NCT01943435N/AOct 1, 2013Cancer Research Network, University of Pittsburgh
NCT01896349N/AApr 1, 2013Federal University of Rio Grande do Sul
NCT02237937Phase 4Sep 1, 2011HolsboerMaschmeyer NeuroChemie GmbH, Max Planck Institute
NCT01268709Phase 2Dec 30, 2010Qom University of Medical Sciences
NCT02901249Phase 4May 1, 2010Federal University of Rio Grande do Sul
NCT02918097Phase 4May 1, 2010Federal University of Rio Grande do Sul
NCT01065649Phase 3Jan 1, 2010Conselho Nacional de Desenvolvimento Científico e Tecnológico, Universidade de Passo Fundo
Showing 20 of 46 trials
Page 1 / 3

Organizations

Research & Development (42)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Institute of Mental Health (NIMH)Government8231989
Columbia UniversityAcademic/Hospital4431997
Sungkyunkwan UniversityAcademic/Hospital4412002
ZalicusFor profit4422007
Cancer Research NetworkAcademic/Hospital3022013
Federal University of Rio Grande do SulAcademic/Hospital3322010
University of California, IrvineAcademic/Hospital3312019
Bioskin GmbHFor profit2022007
Department of Veteran AffairsGovernment2221998
Duke UniversityAcademic/Hospital2212006
Johns Hopkins UniversityAcademic/Hospital2121995
National Institute of Dental and Craniofacial Research (NIDCR)Government2112001
National Institutes of Health (NIH)Government2012006
University of PittsburghAcademic/Hospital2211989
Birjand University of Medical SciencesAcademic/Hospital1112008
Conselho Nacional de Desenvolvimento Científico e TecnológicoGovernment1012010
GlaxoSmithKlineFor profit1012003
Gottfried Wilhelm Leibniz Universität HannoverAcademic/Hospital1112015
HolsboerMaschmeyer NeuroChemie GmbHFor profit1112011
Lancaster General HospitalAcademic/Hospital1112020
42 organizations
Page 1 / 3

Marketing (20)

OrganizationOrg typeRelationshipDate
Ani PharmaceuticalsFor profitMKTGDec 31, 1992
Ani PharmaceuticalsFor profitSYNDec 31, 1992
Aurobindo PharmaFor profitMKTGJun 30, 1997
Aurobindo PharmaFor profitSYNJun 30, 1997
Dr. Reddy's LaboratoriesFor profitMKTGMar 30, 1992
Eli LillyFor profitNDA2Nov 6, 1964
Mayne PharmaFor profitMKTGMar 30, 1992
MylanFor profitMKTGJul 26, 1993
Pharmaceutical AssociatesFor profitMKTGAug 23, 2000
RanbaxyFor profitNDA2Nov 6, 1964
RanbaxyFor profitNDANov 6, 1964
Rising PharmaceuticalsFor profitMKTGJul 26, 1993
Rubicon ResearchFor profitMKTGAug 15, 2023
Rubicon ResearchFor profitSYNAug 15, 2023
Specgx LlcFor profitNDA2Aug 1, 1977
Taro PharmaceuticalsFor profitMKTGJun 20, 2006
Taro PharmaceuticalsFor profitSYNMay 8, 2000
TevaFor profitMKTGMar 27, 1995
Zydus Discovery DMCCFor profitSYNFeb 24, 2021
Zydus Discovery DMCCFor profitMKTGFeb 24, 2021