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flutamide

Trade name: eulexin

Small moleculeapproved

Approved

Jan 27, 1989

Flutamide is a nonsteroidal antiandrogen. In animal studies, flutamide demonstrates potent antiandrogenic effects. It exerts its antiandrogenic action by inhibiting androgen uptake and/or by inhibiting nuclear binding of androgen in target tissues or both. Prostatic carcinoma is known to be androgen-sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen, e.g. castration. Elevations of plasma testosterone and estradiol levels have been noted following flutamide administration. Flutamide blocks the action of both endogenous and exogenous testosterone by binding to the androgen receptor. In addition Flutamide is a potent inhibitor of testosterone-stimulated prostatic DNA synthesis. Moreover, it is capable of inhibiting prostatic nuclear uptake of androgen. Flutamide is used for the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate. — NCATS

Clinical trial activity

72 trials · 89 clinical orgs · 10 marketing orgs

Phase 1
9
Phase 2
50
Phase 3
35
Phase 4
4

Earliest trial started Oct 1, 1994 (NCT00002597)

Timeline

1980s

  1. Jan 27, 1989

    Schering — Earliest FDA Approval

  2. Jan 27, 1989

    Schering — NDA Secondary Org

  3. Jan 27, 1989

    Schering — NDA Organization

  4. Jan 27, 1989

    Schering-Plough — NDA Secondary Org

1990s

  1. Jan 1, 1994

    Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 1996

    Earliest Phase 1 Sponsor(trial)

  3. Jan 1, 1996

    Earliest Phase 2 Sponsor(trial)

2000s

  1. Sep 18, 2001

    Chartwell Pharmaceuticals — Marketing Organization

  2. Sep 18, 2001

    Actavis — Marketing Organization

  3. Sep 18, 2001

    Par Pharmaceuticals — Marketing Organization

  4. Sep 18, 2001

    Waylis Therap — Marketing Organization

  5. Sep 18, 2001

    Fosun — Marketing Organization

  6. Sep 19, 2001

    Cipla — Marketing Organization

  7. May 9, 2003

    Mylan — Marketing Organization

  8. May 9, 2003

    PHARMOBEDIENT — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewJan 27, 1989

Chemistry & pharmacology

Loading structure…

SMILES

CC(C)C(=O)NC1=CC=C(C(=C1)C(F)(F)F)[N+]([O-])=O
Mol. weight
276.2118 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 warningProdrug

Sources

Also known as

  • 1,2,3,4,5,6-hexahydro-1,5-methano-8h- pyrido(1,2-a)(1,5)diazocin-8-one
  • (1r,5s)-1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido[1,2a][1,5]diazocin-8-one
  • (1r,5s)-1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido[1,2a][1,5]diazocin-8-one
  • 3-hydroxy-11-norcytisine
  • 4'-nitro-3'-trifluoromethylisobutyranilide
  • 4'-nitro-3'-trifluoromethylisobutyranilide
  • alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro-m-propionotoluidide
  • alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro-m-propionotoluidide
  • baptitoxine
  • baptitoxine
  • chimax
  • chimax
  • citizine
  • cystisin
  • cytisine
  • cytisine
  • cytisine
  • cytisine
  • cytisine
  • cytisine dihydrochloride, trihydrate
  • cytisine hydrochloride
  • cytisine hydrochloride, hydrate
  • cytisine tetrahydrochloride, trihydrate
  • cytiton
  • drogenil
  • drogenil
  • eulexin
  • eulexin
  • eulexin
  • flutamid
  • flutamid
  • flutamida
  • flutamida
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamide
  • flutamidum
  • flutamidum
  • flutopharm
  • fta
  • fta
  • nfba
  • nfba
  • niftholide
  • niftolid
  • niftolid
  • niftolide
  • niftolide
  • niftolide
  • sch-13521
  • sch-13521
  • sophorine
  • sophorine
  • tabex
  • tsitizin
  • ulexin
  • ulexin

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06694350Phase 2Dec 31, 2024Zhejiang University
NCT06758882Phase 2Nov 25, 2024Azienda Sanitaria Ospedaliera Molinette S. Giovanni Battista
NCT05700903Phase 4Sep 20, 2023University of Colorado, University of Colorado, Denver
NCT05050084Phase 3Nov 11, 2021National Cancer Institute (NCI), NRG Oncology
NCT04787744Phase 2/Phase 3 (Phase 3)Jul 1, 2021Department of Veteran Affairs
NCT05478330N/AJan 13, 2021Zagazig University
NCT04513717Phase 3Dec 15, 2020National Cancer Institute (NCI), NRG Oncology
NCT04597099Early Phase 1 (Phase 1)Oct 20, 2020National Institutes of Health (NIH), University of Virginia
NCT04248621Phase 4Jan 23, 2020Eulji University, Wonju Christian Hospital
NCT03678025Phase 3Sep 17, 2018National Cancer Institute (NCI), Southwest Oncology Group
NCT03488810Phase 3Aug 1, 2018Centre Georges Francois Leclerc, European Organisation for Research and Treatment of Cancer, Grenoble Alps University
NCT03507608Early Phase 1 (Phase 1)Jul 1, 2018Johns Hopkins University
NCT02797587Phase 2/Phase 3 (Phase 3)Jul 1, 2017Boston University, National Institute on Alcohol Abuse and Alcoholism (NIAAA)
NCT02957786Phase 3Jun 1, 2017Brunel University, Lakes District Health Board, University of Auckland
NCT02799706Phase 3Apr 1, 2017European Organisation for Research and Treatment of Cancer, Humboldt University
NCT03070886Phase 2/Phase 3 (Phase 3)Jan 16, 2017National Cancer Institute (NCI), NRG Oncology
NCT02918968Phase 4Nov 2, 2016Astellas, Medivation
NCT02742675Phase 2Mar 1, 2016Fudan University
NCT02585024Phase 1Feb 1, 2016University of Auckland
NCT02346578N/AJan 1, 2015Astellas, Osaka City University
Showing 20 of 72 trials
Page 1 / 4

Organizations

Research & Development (89)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government32631994
Radiation Therapy Oncology GroupAcademic/Hospital111121994
NRG OncologyAcademic/Hospital8322002
Harvard UniversityAcademic/Hospital6121995
Southwest Oncology GroupAcademic/Hospital6221995
Canadian Cancer Trials GroupAcademic/Hospital5421995
Eastern Cooperative Oncology GroupAcademic/Hospital4111995
National Institutes of Health (NIH)Government4121996
University of Texas at HoustonAcademic/Hospital4321996
Cancer and Leukemia Group B (CALGB)Academic/Hospital3011996
European Organisation for Research and Treatment of CancerAcademic/Hospital3311997
Mayo ClinicAcademic/Hospital3122000
TakedaFor profit3321996
Temple UniversityAcademic/Hospital3012002
Thomas Jefferson UniversityAcademic/Hospital3022001
University of MichiganAcademic/Hospital3022000
University of TorontoAcademic/Hospital3011995
University of VirginiaAcademic/Hospital3322006
University of WashingtonAcademic/Hospital3221997
AstellasFor profit2122015
89 organizations
Page 1 / 5

Marketing (11)

OrganizationOrg typeRelationshipDate
ActavisFor profitMKTGSep 18, 2001
Chartwell PharmaceuticalsFor profitMKTGSep 18, 2001
CiplaFor profitMKTGSep 19, 2001
FosunFor profitMKTGSep 18, 2001
MylanFor profitMKTGMay 9, 2003
PHARMOBEDIENTFor profitMKTGMay 9, 2003
Par PharmaceuticalsFor profitMKTGSep 18, 2001
ScheringFor profitNDA2Jan 27, 1989
ScheringFor profitNDAJan 27, 1989
Schering-PloughFor profitNDA2Jan 27, 1989
Waylis TherapFor profitMKTGSep 18, 2001