nilutamide
Trade name: nilandron
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
Earliest trial started Mar 1, 1995 (NCT00002633)
Timeline
1990s
- Jan 1, 1995
Earliest Phase 3 Sponsor(trial)
- Sep 19, 1996
Roussel-Uclaf — Earliest FDA Approval
- Sep 19, 1996
Roussel-Uclaf — NDA Organization
- Sep 19, 1996
Advanz Pharma — NDA Secondary Org
- Sep 19, 1996
Advanz Pharma — Marketing Organization
2010s
- Jul 15, 2016
Ani Pharmaceuticals — Marketing Organization
Indications
Approved for
Mechanism of action
- Androgen ReceptorANTAGONIST
AR antagonist
Approval history
- approvedSep 19, 1996
Chemistry & pharmacology
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
Sources
- WikipediaNilutamide ↗
- NCATS51G6I8B902 ↗
- ChEMBLCHEMBL1274 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT04787744 | Phase 2/Phase 3 (Phase 3) | Jul 1, 2021 | Department of Veteran Affairs |
| NCT03678025 | Phase 3 | Sep 17, 2018 | National Cancer Institute (NCI), Southwest Oncology Group |
| NCT03070886 | Phase 2/Phase 3 (Phase 3) | Jan 16, 2017 | National Cancer Institute (NCI), NRG Oncology |
| NCT00918385 | Phase 2 | May 1, 2009 | Bristol-Myers Squibb, Duke University |
| NCT00512668 | Phase 1 | Sep 1, 2007 | National Cancer Institute (NCI), University of Texas at Houston |
| NCT00055731 | Phase 3 | Nov 1, 2002 | Institut Gustave Roussy, UNICANCER |
| NCT00028769 | Phase 2 | Dec 1, 2001 | National Cancer Institute (NCI), Southwest Oncology Group, University of Michigan |
| NCT00020254 | Phase 2 | Jun 1, 2000 | National Cancer Institute (NCI) |
| NCT00003653 | Phase 3 | Jan 1, 1999 | Canadian Cancer Trials Group, National Cancer Institute (NCI), Southwest Oncology Group, University of Toronto, University of Washington |
| NCT00002855 | Phase 3 | Aug 1, 1996 | National Cancer Institute (NCI), University of Texas at Houston |
| NCT00002633 | Phase 3 | Mar 1, 1995 | Canadian 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 |
Organizations
Research & Development (19)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| National Cancer Institute (NCI) | Government | 8 | 2 | 3 | 1995 |
| Southwest Oncology Group | Academic/Hospital | 4 | 2 | 2 | 1995 |
| Canadian Cancer Trials Group | Academic/Hospital | 2 | 2 | 1 | 1995 |
| University of Texas at Houston | Academic/Hospital | 2 | 1 | 2 | 1996 |
| University of Toronto | Academic/Hospital | 2 | 0 | 1 | 1995 |
| Bristol-Myers Squibb | For profit | 1 | 0 | 1 | 2009 |
| Department of Veteran Affairs | Government | 1 | 1 | 1 | 2021 |
| Duke University | Academic/Hospital | 1 | 1 | 1 | 2009 |
| Eastern Cooperative Oncology Group | Academic/Hospital | 1 | 0 | 1 | 1995 |
| Institut Gustave Roussy | Academic/Hospital | 1 | 0 | 1 | 2002 |
| Medical Research Council | Government | 1 | 0 | 1 | 1995 |
| Michael Reese Hospital and Medical Center | Academic/Hospital | 1 | 0 | 1 | 1995 |
| NRG Oncology | Academic/Hospital | 1 | 1 | 1 | 2017 |
| UNICANCER | Academic/Hospital | 1 | 1 | 1 | 2002 |
| United States Army | Government | 1 | 0 | 1 | 1995 |
| University of Michigan | Academic/Hospital | 1 | 0 | 1 | 2001 |
| University of Pennsylvania | Academic/Hospital | 1 | 0 | 1 | 1995 |
| University of Washington | Academic/Hospital | 1 | 0 | 1 | 1999 |
| Velindre NHS Trust | Academic/Hospital | 1 | 0 | 1 | 1995 |
Marketing (6)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Advanz Pharma | For profit | NDA2 | Sep 19, 1996 |
| Advanz Pharma | For profit | MKTG | Sep 19, 1996 |
| Advanz Pharma | For profit | SYN | Sep 19, 1996 |
| Ani Pharmaceuticals | For profit | MKTG | Jul 15, 2016 |
| Ani Pharmaceuticals | For profit | SYN | Jul 15, 2016 |
| Roussel-Uclaf | For profit | NDA | Sep 19, 1996 |