doxepin

Trade name: sinequan

Small moleculeapproved

Approved

Sep 23, 1969

Doxepin is a dibenzoxepin tricyclic antidepressant marketed worldwide. It is a white crystalline solid readily soluble in water, lower alcohols and chloroform. The mechanism of action of doxepin is not definitely known. It is not a central nervous system stimulant nor a monoamine oxidase inhibitor. The current hypothesis is that the clinical effects are due, at least in part, to influences on the adrenergic activity at the synapses so that deactivation of norepinephrine by reuptake into the nerve terminals is prevented. Antidepressants may increase risk of suicidal thinking and behavior (suicidality) in children, adolescents, and young adults (18–24 years of age) with major depressive disorder and other psychiatric disorders. Drowsiness is the most commonly noticed side effect. This tends to disappear as therapy is continued. Other infrequently reported CNS side effects are confusion, disorientation, hallucinations, numbness, paresthesias, ataxia, extrapyramidal symptoms, seizures, tardive dyskinesia, and tremor. : Cardiovascular effects including hypotension, hypertension, and tachycardia have been reported occasionally. Skin rash, edema, photosensitization, and pruritus have occasionally occurred. Eosinophilia has been reported in a few patients. There have been occasional reports of bone marrow depression manifesting as agranulocytosis, leukopenia, thrombocytopenia, and purpura. Doxepin is used to treat depression, anxiety disorders, itchiness, trouble sleeping, and as a second-line treatment of chronic idiopathic urticaria (hives). Its oral formulations are FDA-approved for the treatment of depression, anxiety, and insomnia and its topical formulations are FDA-approved the short-term management (up to 8 days) of atopic dermatitis and lichen simplex chronicus. Whereas in Australia and the UK, the only licensed indication(s) is/are in the treatment of major depression and pruritus in eczema, respectively. — NCATS

Clinical trial activity

17 trials · 18 clinical orgs · 39 marketing orgs

Phase 1
1
Phase 2
7
Phase 3
4
Phase 4
3

Earliest trial started Jul 1, 2006 (NCT00755495)

Timeline

1960s

  1. Sep 23, 1969

    Roche — Earliest FDA Approval

  2. Sep 23, 1969

    Pfizer — NDA Secondary Org

  3. Sep 23, 1969

    Roche — NDA Organization

1970s

  1. Jan 31, 1972

    New River Pharmaceuticals — NDA Secondary Org

1980s

  1. May 13, 1986

    Mylan — Marketing Organization

  2. May 15, 1986

    Sandoz — Marketing Organization

  3. Apr 30, 1987

    Watson Pharmaceuticals — Marketing Organization

  4. Nov 9, 1987

    Par Pharmaceuticals — Marketing Organization

  5. Nov 9, 1987

    Teva — Marketing Organization

  6. Feb 18, 1988

    Sun Pharmaceuticals — Marketing Organization

  7. Jul 20, 1988

    Wockhardt — Marketing Organization

  8. Jul 20, 1988

    Xttrium Laboratories — Marketing Organization

1990s

  1. Dec 28, 1990

    Puracap Pharmaceutical — Marketing Organization

  2. Apr 1, 1994

    Mylan — NDA Secondary Org

  3. Dec 29, 1998

    Lannett Company, Inc. — Marketing Organization

2000s

  1. Jan 15, 2004

    Pharmaceutical Associates — Marketing Organization

  2. Jan 1, 2006

    Earliest Phase 2 Sponsor(trial)

2010s

  1. Jan 1, 2010

    Earliest Phase 3 Sponsor(trial)

  2. Mar 17, 2010

    Currax Pharmaceuticals — Marketing Organization

  3. Mar 17, 2010

    Pernix — NDA Secondary Org

  4. Mar 17, 2010

    Currax Pharmaceuticals — NDA Secondary Org

  5. Jan 1, 2011

    Earliest Phase 1 Sponsor(trial)

  6. Feb 22, 2013

    Zydus Discovery DMCC — Marketing Organization

  7. Jul 26, 2013

    Actavis — Marketing Organization

  8. Jan 20, 2016

    Apicore — Marketing Organization

  9. Jun 28, 2017

    Amneal Pharmaceuticals — Marketing Organization

  10. Mar 27, 2019

    Aurobindo Pharma — Marketing Organization

  11. Sep 13, 2019

    Ajanta Pharma Ltd — Marketing Organization

2020s

  1. Jul 1, 2020

    Taro Pharmaceuticals — Marketing Organization

  2. Jul 24, 2020

    Strides Pharma Science — Marketing Organization

  3. Jul 28, 2020

    Contract Pharmacal — Marketing Organization

  4. Sep 4, 2020

    Upsher-Smith Laboratories — Marketing Organization

  5. Sep 4, 2020

    Chartwell Pharmaceuticals — Marketing Organization

  6. Oct 16, 2020

    Epic Pharma Llc — Marketing Organization

  7. Mar 1, 2021

    Leading Pharma Llc — Marketing Organization

  8. Apr 1, 2021

    Appco Pharma — Marketing Organization

  9. Apr 21, 2021

    Alembic — Marketing Organization

  10. Feb 9, 2022

    Mankind Pharma — Marketing Organization

  11. Mar 14, 2022

    Jubilant Innovation Ltd. — Marketing Organization

  12. Apr 19, 2022

    Edenbridge Pharms — Marketing Organization

  13. Jun 24, 2022

    MSN Laboratories — Marketing Organization

  14. Jun 27, 2023

    Micro Labs Ltd India — Marketing Organization

  15. Aug 21, 2023

    Unique Pharmaceuticals Ltd, India — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedSep 23, 1969

Chemistry & pharmacology

Loading structure…

SMILES

CN(C)CCC=C1c2ccccc2COc2ccccc21
Mol. weight
279.38 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral, Topical
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

Yes

Black box warning

Sources

Also known as

  • doxepin
  • doxepin
  • doxepin
  • doxepin
  • doxepin
  • doxepin hcl
  • doxepin hcl
  • doxepin hcl
  • doxepin hydrochloride
  • doxepin hydrochloride
  • doxepin hydrochloride
  • doxepin hydrochloride
  • doxepin hydrochloride
  • quitaxon
  • quitaxon
  • silenor
  • silenor
  • silenor
  • sinepin
  • sinequan
  • sinequan
  • xepin
  • xepin
  • zonalon
  • zonalon

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06017895N/ANov 1, 2023Southern Medical University
NCT05607056N/ANov 27, 2022Medical University of Sofia, Neopharm
NCT05115136Phase 3Nov 8, 2021State University of New York, Syracuse
NCT04554888N/ANov 1, 2020Aalborg University
NCT04588532N/AOct 31, 2020Aalborg University
NCT03943407N/AJun 30, 2019Aalborg University
NCT03758079Phase 4Jun 1, 2018University of Balamand
NCT02447211Phase 2May 1, 2015Iran University of Medical Sciences, Isfahan Milad Hospital, Isfahan University
NCT02374567Phase 3Jan 1, 2015Gottfried Wilhelm Leibniz Universität Hannover
NCT02353299Phase 4Jan 1, 2015Henry Ford Health System, Pernix
NCT02229539Phase 3Nov 1, 2014Mayo Clinic, National Cancer Institute (NCI)
NCT02062632N/AApr 14, 2014Mayo Clinic, National Cancer Institute (NCI)
NCT01489982Early Phase 1 (Phase 1)Jan 1, 2011McGill University
NCT01268709Phase 2Dec 30, 2010Qom University of Medical Sciences
NCT01156142Phase 3Dec 1, 2010Mayo Clinic, National Cancer Institute (NCI)
NCT00465972Phase 4Mar 1, 2007Duke University
NCT00755495Phase 2Jul 1, 2006Takeda
Showing 17 of 17 trials
Page 1 / 1

Organizations

Research & Development (18)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Aalborg UniversityAcademic/Hospital3312019
Mayo ClinicAcademic/Hospital3122010
National Cancer Institute (NCI)Government3222010
Duke UniversityAcademic/Hospital1112007
Gottfried Wilhelm Leibniz Universität HannoverAcademic/Hospital1112015
Henry Ford Health SystemAcademic/Hospital1012015
Iran University of Medical SciencesAcademic/Hospital1012015
Isfahan Milad HospitalAcademic/Hospital1012015
Isfahan UniversityAcademic/Hospital1112015
McGill UniversityAcademic/Hospital1112011
Medical University of SofiaAcademic/Hospital1012022
NeopharmFor profit1112022
PernixFor profit1112015
Qom University of Medical SciencesAcademic/Hospital1112010
Southern Medical UniversityAcademic/Hospital1112023
State University of New York, SyracuseAcademic/Hospital1112021
TakedaFor profit1112006
University of BalamandAcademic/Hospital1112018
18 organizations
Page 1 / 1

Marketing (52)

OrganizationOrg typeRelationshipDate
ActavisFor profitMKTGJul 26, 2013
Ajanta Pharma LtdFor profitMKTGSep 13, 2019
AlembicFor profitMKTGApr 21, 2021
AlembicFor profitSYNApr 21, 2021
Amneal PharmaceuticalsFor profitMKTGJun 28, 2017
Amneal PharmaceuticalsFor profitSYNAug 16, 2023
ApicoreFor profitMKTGJan 20, 2016
Appco PharmaFor profitMKTGApr 1, 2021
Aurobindo PharmaFor profitMKTGMar 27, 2019
Chartwell PharmaceuticalsFor profitMKTGSep 4, 2020
Contract PharmacalFor profitMKTGJul 28, 2020
Currax PharmaceuticalsFor profitMKTGMar 17, 2010
Currax PharmaceuticalsFor profitNDA2Mar 17, 2010
DAVA PharmaceuticalsFor profitMKTG
Edenbridge PharmsFor profitMKTGApr 19, 2022
Epic Pharma LlcFor profitMKTGOct 16, 2020
Jubilant Innovation Ltd.For profitMKTGMar 14, 2022
Lannett Company, Inc.For profitMKTGDec 29, 1998
Leading Pharma LlcFor profitMKTGMar 1, 2021
Leading Pharma LlcFor profitMKTGMar 1, 2021
MSN LaboratoriesFor profitMKTGJun 24, 2022
Mankind PharmaFor profitMKTGFeb 9, 2022
Micro Labs Ltd IndiaFor profitMKTGJun 27, 2023
MylanFor profitMKTGMay 13, 1986
MylanFor profitSYNMay 13, 1986
MylanFor profitNDA2Apr 1, 1994
New River PharmaceuticalsFor profitNDA2Jan 31, 1972
Par PharmaceuticalsFor profitMKTGNov 9, 1987
Par PharmaceuticalsFor profitSYNJul 24, 2020
PernixFor profitNDA2Mar 17, 2010
PfizerFor profitNDA2Sep 23, 1969
Pharmaceutical AssociatesFor profitMKTGJan 15, 2004
Puracap PharmaceuticalFor profitMKTGDec 28, 1990
Quantum PharmaceuticalFor profitMKTG
RocheFor profitNDASep 23, 1969
SandozFor profitMKTGMay 15, 1986
Strides Pharma ScienceFor profitMKTGJul 24, 2020
Strides Pharma ScienceFor profitMKTGJul 24, 2020
Sun PharmaceuticalsFor profitMKTGFeb 18, 1988
Taro PharmaceuticalsFor profitMKTGJul 1, 2020
Taro PharmaceuticalsFor profitSYNJul 1, 2020
TevaFor profitSYNNov 9, 1987
TevaFor profitSYNMar 29, 1991
TevaFor profitMKTGNov 9, 1987
Unique Pharmaceuticals Ltd, IndiaFor profitMKTGAug 21, 2023
Upsher-Smith LaboratoriesFor profitMKTGSep 4, 2020
Watson PharmaceuticalsFor profitMKTGApr 30, 1987
WockhardtFor profitMKTGJul 20, 1988
Xttrium LaboratoriesFor profitMKTGJul 20, 1988
Zydus Discovery DMCCFor profitMKTGFeb 22, 2013
Zydus Discovery DMCCFor profitSYNMar 21, 2023
Zydus Discovery DMCCFor profitSYNAug 16, 2023