nilutamide

Trade name: nilandron

Small moleculeapproved

Approved

Sep 19, 1996

Nilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration. The relative binding affinity of nilutamide at the androgen receptor is less than that of bicalutamide, but similar to that of hydroxuflutamide. Nilutamide competes with androgen for the binding of androgen receptors, consequently blocking the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. This blockade of androgen receptors may result in growth arrest or transient tumor regression through inhibition of androgen-dependent DNA and protein synthesis. Nilutamide is used in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2). Nilutamide is sold under the brand names Nilandron (US), Anandron (CA)). — NCATS

Clinical trial activity

11 trials · 19 clinical orgs · 3 marketing orgs

Phase 1
1
Phase 2
8
Phase 3
7
Phase 4
0

Earliest trial started Mar 1, 1995 (NCT00002633)

Timeline

1990s

  1. Jan 1, 1995

    Earliest Phase 3 Sponsor(trial)

  2. Sep 19, 1996

    Roussel-Uclaf — Earliest FDA Approval

  3. Sep 19, 1996

    Roussel-Uclaf — NDA Organization

  4. Sep 19, 1996

    Advanz Pharma — NDA Secondary Org

  5. Sep 19, 1996

    Advanz Pharma — Marketing Organization

2000s

  1. Jan 1, 2000

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2007

    Earliest Phase 1 Sponsor(trial)

2010s

  1. Jul 15, 2016

    Ani Pharmaceuticals — Marketing Organization

Indications

Mechanism of action

Approval history

  • approvedSep 19, 1996

Chemistry & pharmacology

Loading structure…

SMILES

CC1(C)NC(=O)N(C1=O)C2=CC(=C(C=C2)[N+]([O-])=O)C(F)(F)F
Mol. weight
317.2207 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

  • 2,4-imidazolidinedione, 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-
  • 5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedione
  • 5,5-dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin
  • 5,5-dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin
  • anadron
  • anandron
  • anandron
  • aventis behring brand of nilutamide
  • aventis brand of nilutamide
  • hoechst brand of nilutamide
  • nilandron
  • nilandron
  • nilandron
  • nilandron
  • nilandron
  • nilandrone
  • nilutamida
  • nilutamida
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamide
  • nilutamidum
  • nilutamidum
  • ru 23908
  • ru-23908
  • ru-23908
  • ru-23908
  • ru 23908-10

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT04787744Phase 2/Phase 3 (Phase 3)Jul 1, 2021Department of Veteran Affairs
NCT03678025Phase 3Sep 17, 2018National Cancer Institute (NCI), Southwest Oncology Group
NCT03070886Phase 2/Phase 3 (Phase 3)Jan 16, 2017National Cancer Institute (NCI), NRG Oncology
NCT00918385Phase 2May 1, 2009Bristol-Myers Squibb, Duke University
NCT00512668Phase 1Sep 1, 2007National Cancer Institute (NCI), University of Texas at Houston
NCT00055731Phase 3Nov 1, 2002Institut Gustave Roussy, UNICANCER
NCT00028769Phase 2Dec 1, 2001National Cancer Institute (NCI), Southwest Oncology Group, University of Michigan
NCT00020254Phase 2Jun 1, 2000National Cancer Institute (NCI)
NCT00003653Phase 3Jan 1, 1999Canadian Cancer Trials Group, National Cancer Institute (NCI), Southwest Oncology Group, University of Toronto, University of Washington
NCT00002855Phase 3Aug 1, 1996National Cancer Institute (NCI), University of Texas at Houston
NCT00002633Phase 3Mar 1, 1995Canadian Cancer Trials Group, Eastern Cooperative Oncology Group, Medical Research Council, Michael Reese Hospital and Medical Center, National Cancer Institute (NCI), Southwest Oncology Group, United States Army, University of Pennsylvania, University of Toronto, Velindre NHS Trust
Showing 11 of 11 trials
Page 1 / 1

Organizations

Research & Development (19)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government8231995
Southwest Oncology GroupAcademic/Hospital4221995
Canadian Cancer Trials GroupAcademic/Hospital2211995
University of Texas at HoustonAcademic/Hospital2121996
University of TorontoAcademic/Hospital2011995
Bristol-Myers SquibbFor profit1012009
Department of Veteran AffairsGovernment1112021
Duke UniversityAcademic/Hospital1112009
Eastern Cooperative Oncology GroupAcademic/Hospital1011995
Institut Gustave RoussyAcademic/Hospital1012002
Medical Research CouncilGovernment1011995
Michael Reese Hospital and Medical CenterAcademic/Hospital1011995
NRG OncologyAcademic/Hospital1112017
UNICANCERAcademic/Hospital1112002
United States ArmyGovernment1011995
University of MichiganAcademic/Hospital1012001
University of PennsylvaniaAcademic/Hospital1011995
University of WashingtonAcademic/Hospital1011999
Velindre NHS TrustAcademic/Hospital1011995
19 organizations
Page 1 / 1

Marketing (6)

OrganizationOrg typeRelationshipDate
Advanz PharmaFor profitNDA2Sep 19, 1996
Advanz PharmaFor profitMKTGSep 19, 1996
Advanz PharmaFor profitSYNSep 19, 1996
Ani PharmaceuticalsFor profitMKTGJul 15, 2016
Ani PharmaceuticalsFor profitSYNJul 15, 2016
Roussel-UclafFor profitNDASep 19, 1996