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cyclobenzaprine

Trade name: flexeril

Small moleculeapproved

Approved

Aug 26, 1977

Cyclobenzaprine is a centrally-acting muscle relaxant which boosts levels of norepinephrine and binds to serotonin receptors in the brain to reduce spasm. Cytochromes P-450 3A4, 1A2, and, to a lesser extent, 2D6, mediate N-demethylation, one of the oxidative pathways for cyclobenzaprine. Cyclobenzaprine relieves skeletal muscle spasm of local origin without interfering with muscle function. Drowsiness, fatigue and sedation (up to 40%) is the most common side effect of Cyclobenzaprine. It may have life-threatening interactions with monoamine oxidase (MAO) inhibitors. Postmarketing cases of serotonin syndrome have been reported during combined use of cyclobenzaprine and other drugs such as selective serotonin reuptake inhibitors (SSRIs), serotonin norepinephrine reuptake inhibitors (SNRIs), tricyclic antidepressants (TCAs), tramadol, bupropion, meperidine, verapamil, or MAO inhibitors. — NCATS

Clinical trial activity

51 trials · 42 clinical orgs · 31 marketing orgs

Phase 1
14
Phase 2
33
Phase 3
22
Phase 4
3

Earliest trial started Nov 1, 1988 (NCT00913419)

Timeline

1970s

  1. Aug 26, 1977

    Janssen Pharmaceutica NV — Earliest FDA Approval

  2. Aug 26, 1977

    Johnson and Johnson — NDA Secondary Org

  3. Aug 26, 1977

    Janssen Pharmaceutica NV — NDA Organization

1980s

  1. Jan 1, 1988

    Sandoz — Earliest Phase 1 Sponsor(trial)

  2. Feb 29, 1988

    Actavis — Marketing Organization

1990s

  1. May 31, 1991

    Rising Pharmaceuticals — Marketing Organization

  2. May 31, 1991

    Mylan — Marketing Organization

  3. Nov 19, 1991

    Chartwell Pharmaceuticals — Marketing Organization

  4. Nov 19, 1991

    Upsher-Smith Laboratories — Marketing Organization

  5. Nov 19, 1991

    AiPing Pharm Inc — Marketing Organization

  6. Nov 27, 1991

    Watson Pharmaceuticals — Marketing Organization

  7. Feb 26, 1993

    Sandoz — Marketing Organization

  8. May 23, 1995

    Frontida BioPharm — Marketing Organization

  9. May 23, 1995

    ANDA Repository — Marketing Organization

  10. Sep 29, 1995

    Pliva — Marketing Organization

2000s

  1. Jan 1, 2003

    Earliest Phase 2 Sponsor(trial)

  2. Oct 4, 2005

    Oxford Pharmaceuticals — Marketing Organization

  3. Apr 19, 2006

    Jubilant Innovation Ltd. — Marketing Organization

  4. Feb 1, 2007

    Teva — NDA Secondary Org

  5. Feb 28, 2007

    Prinston Inc — Marketing Organization

  6. Apr 18, 2008

    Alembic — Marketing Organization

  7. Apr 18, 2008

    Orit Labs Llc — Marketing Organization

  8. May 12, 2008

    Sun Pharmaceuticals — Marketing Organization

  9. Sep 26, 2008

    Aurobindo Pharma — Marketing Organization

2010s

  1. Jan 1, 2010

    Earliest Phase 3 Sponsor(trial)

  2. Jul 23, 2010

    Invagen Pharms — Marketing Organization

  3. Feb 28, 2011

    Kvk Tech Inc — Marketing Organization

  4. Jan 31, 2013

    TWi Biotechnology, Inc. — Marketing Organization

  5. Jul 26, 2013

    Par Pharmaceuticals — Marketing Organization

  6. May 31, 2017

    Rubicon Research — Marketing Organization

  7. Jul 24, 2018

    Apotex — Marketing Organization

2020s

  1. Jul 6, 2020

    Unichem — Marketing Organization

  2. Jul 22, 2024

    Macleods Pharmaceuticals, Ltd — Marketing Organization

  3. Aug 27, 2024

    Novast Labs — Marketing Organization

  4. Sep 12, 2024

    Graviti Pharmaceuticals — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewAug 26, 1977

Chemistry & pharmacology

Loading structure…

SMILES

CN(C)CCC=C1c2ccccc2C=Cc2ccccc21
Mol. weight
275.4 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

Also known as

  • (3-dibenzo[a,d]cyclohepten-5-ylidene-propyl)-dimethyl-amine
  • (3-dibenzo[a,d]cyclohepten-5-ylidene-propyl)-dimethyl-amine
  • amrix
  • amrix
  • ciclobenzaprina
  • ciclobenzaprina
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine
  • cyclobenzaprine hcl
  • cyclobenzaprine hcl
  • cyclobenzaprine hcl
  • cyclobenzaprine hydrochloride
  • cyclobenzaprine hydrochloride
  • cyclobenzaprine hydrochloride
  • cyclobenzaprine hydrochloride
  • cyclobenzaprine hydrochloride
  • cyclobenzaprine hydrochloride
  • cyclobenzaprinum
  • cyclobenzaprinum
  • flexeril
  • flexeril
  • flexeril
  • flexeril
  • lisseril
  • mk-130
  • mk-130
  • mk-1308
  • mk-130 [as the base]
  • mk-130 [as the base]
  • n,n-dimethyl-3-(dibenzo(a,d)cycloheptene-4-ylidene)propylamine
  • n,n-dimethyl-5h-dibenzo(a,d)cycloheptene-delta(5,gamma)-propylamine
  • n,n-dimethyl-5h-dibenzo(a,d)cycloheptene-delta(5,gamma)-propylamine
  • n,n-dimethyl-5h-dibenzo(a,d)cycloheptene-δ5,γ-propylamine
  • n,n-dimethyl-5h-dibenzo(a,d)cycloheptene-δ5,γ-propylamine
  • proheptatrien
  • proheptatriene
  • tnx-102
  • tnx-102

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06636786Phase 2Oct 31, 2024Department of Defense, Mclean Hospital, Rowan University, Tonix Pharmaceuticals, University of North Carolina at Chapel Hill
NCT05683574Phase 3Jun 30, 2024Eurofarma Laboratorios S.A.
NCT05472090Phase 2Aug 18, 2022Tonix Pharmaceuticals
NCT05372887Phase 2Jun 30, 2022Tonix Pharmaceuticals
NCT05273749Phase 3Apr 6, 2022Tonix Pharmaceuticals
NCT04843098Phase 1/Phase 2 (Phase 2)Apr 30, 2021Government of China
NCT04626479Phase 1/Phase 2 (Phase 2)Dec 17, 2020Merck
NCT04626518Phase 1/Phase 2 (Phase 2)Dec 17, 2020Merck
NCT04671082Phase 3Dec 15, 2020Neurana Pharmaceuticals, Inc.
NCT04508621Phase 3Sep 1, 2020Tonix Pharmaceuticals
NCT04305041Phase 1/Phase 2 (Phase 2)Jul 3, 2020Merck
NCT04407377Phase 1May 20, 2020Neurana Pharmaceuticals, Inc.
NCT04172831Phase 3Dec 31, 2019Tonix Pharmaceuticals
NCT05544656Phase 3Dec 13, 2019Semmelweis University
NCT04164719Phase 1Oct 14, 2019Tonix Pharmaceuticals
NCT03841773Phase 3Mar 7, 2019Tonix Pharmaceuticals
NCT03516981Phase 2Sep 28, 2018Merck
NCT03508700Phase 3Apr 19, 2018Tonix Pharmaceuticals
NCT03443960Phase 1Jan 29, 2018Tonix Pharmaceuticals
NCT03127592Phase 3Dec 1, 2017Apsen Farmaceutica S.A.
Showing 20 of 51 trials
Page 1 / 3

Organizations

Research & Development (42)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Tonix PharmaceuticalsFor profit232232011
Premier Research GroupFor profit6022013
MerckFor profit5522017
PharmaNetFor profit4012011
Neurana Pharmaceuticals, Inc.For profit3322017
EMS S/AFor profit2212017
Eurofarma Laboratorios S.A.For profit2212013
Apsen Farmaceutica S.A.For profit1112017
AstellasFor profit1012010
CephalonFor profit1012009
Cognitive Research CorporationFor profit1012017
Collaborative Neuroscience NetworkFor profit1012017
Damon Runyon Cancer Research FoundationAcademic/Hospital1012013
Department of DefenseGovernment1012024
Faculdade de Medicina do ABCAcademic/Hospital1012013
Federal University of Juiz de ForaAcademic/Hospital1012013
Government of ChinaGovernment1112021
Hospital Santa Marcelina, Sao Paulo, BrasilAcademic/Hospital1012013
Instituto Brasileiro de OsteopatiaAcademic/Hospital1112012
Kennedy Medical GroupAcademic/Hospital1112010
42 organizations
Page 1 / 3

Marketing (35)

OrganizationOrg typeRelationshipDate
ANDA RepositoryFor profitMKTGMay 23, 1995
ActavisFor profitMKTGFeb 29, 1988
AiPing Pharm IncFor profitMKTGNov 19, 1991
AlembicFor profitMKTGApr 18, 2008
ApotexFor profitMKTGJul 24, 2018
ApotexFor profitSYNJul 24, 2018
Aurobindo PharmaFor profitMKTGSep 26, 2008
Chartwell PharmaceuticalsFor profitMKTGNov 19, 1991
Frontida BioPharmFor profitMKTGMay 23, 1995
Graviti PharmaceuticalsFor profitMKTGSep 12, 2024
Invagen PharmsFor profitMKTGJul 23, 2010
Janssen Pharmaceutica NVFor profitNDAAug 26, 1977
Johnson and JohnsonFor profitNDA2Aug 26, 1977
Jubilant Innovation Ltd.For profitMKTGApr 19, 2006
Kvk Tech IncFor profitMKTGFeb 28, 2011
Macleods Pharmaceuticals, LtdFor profitMKTGJul 22, 2024
MylanFor profitMKTGMay 31, 1991
Novast LabsFor profitMKTGAug 27, 2024
Orit Labs LlcFor profitMKTGApr 18, 2008
Oxford PharmaceuticalsFor profitMKTGOct 4, 2005
Par PharmaceuticalsFor profitMKTGJul 26, 2013
PlivaFor profitMKTGSep 29, 1995
Prinston IncFor profitMKTGFeb 28, 2007
Rising PharmaceuticalsFor profitMKTGMay 31, 1991
Rising PharmaceuticalsFor profitSYNMay 31, 1991
Rubicon ResearchFor profitMKTGMay 31, 2017
Rubicon ResearchFor profitSYNMay 31, 2017
SandozFor profitMKTGFeb 26, 1993
Sun PharmaceuticalsFor profitMKTGMay 12, 2008
TWi Biotechnology, Inc.For profitMKTGJan 31, 2013
TevaFor profitNDA2Feb 1, 2007
UnichemFor profitMKTGJul 6, 2020
UnichemFor profitSYNJul 6, 2020
Upsher-Smith LaboratoriesFor profitMKTGNov 19, 1991
Watson PharmaceuticalsFor profitMKTGNov 27, 1991