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Details

Stereochemistry ACHIRAL
Molecular Formula C12H10F3N3O4
Molecular Weight 317.2207
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NILUTAMIDE

SMILES

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

InChI

InChIKey=XWXYUMMDTVBTOU-UHFFFAOYSA-N
InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)

HIDE SMILES / InChI

Description

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)).

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NILANDRON
PubMed

PubMed

TitleDatePubMed
Flare Associated with LHRH-Agonist Therapy.
2001
Androgen deprivation and other treatments for advanced prostate cancer.
2001
Therapeutic androgen receptor ligands.
2003
Role of 5 alpha-reductase inhibitors in the management of prostate cancer.
2006
Androgenic and antiandrogenic effects and expression of androgen receptor in mouse embryonic stem cells.
2006 Apr
Androgen receptor is responsible for rat organic cation transporter 2 gene regulation but not for rOCT1 and rOCT3.
2006 Apr
The role of steroids in follicular growth.
2006 Apr 10
Antiandrogen treatments in locally advanced prostate cancer: are they all the same?
2006 Aug
Ginsenoside Re, a main phytosterol of Panax ginseng, activates cardiac potassium channels via a nongenomic pathway of sex hormones.
2006 Dec
Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review.
2006 Jun
Recent progress in hormonal therapy for advanced prostate cancer.
2006 May
Combined androgen blockade: an update.
2006 May
Bioactivation and hepatotoxicity of nitroaromatic drugs.
2006 Oct
[Keyrole of endocrinology in the victory against prostate cancer].
2006 Sep
A bifunctional colchicinoid that binds to the androgen receptor.
2007 Aug
Role of vaccine therapy in cancer: biology and practice.
2007 Dec
Signaling pathway of nitric oxide production induced by ginsenoside Rb1 in human aortic endothelial cells: a possible involvement of androgen receptor.
2007 Feb 16
New therapeutic targets in the treatment of prostate cancer.
2007 Jan
Antiandrogenic activity of pyrethroid pesticides and their metabolite in reporter gene assay.
2007 Jan
A novel synthetic compound that interrupts androgen receptor signaling in human prostate cancer cells.
2007 Jul
Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.
2007 Jun 1
Long-term effectiveness of luteinizing hormone-releasing hormone agonist or antiandrogen monotherapy in elderly men with localized prostate cancer (T1-2): a retrospective study.
2007 Mar
Combined androgen blockade in advanced prostate cancer: looking back to move forward.
2007 Sep
Androgen receptor functional analyses by high throughput imaging: determination of ligand, cell cycle, and mutation-specific effects.
2008
Maximal androgen blockade for advanced prostate cancer.
2008 Apr
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
The androgen receptor can signal through Wnt/beta-Catenin in prostate cancer cells as an adaptation mechanism to castration levels of androgens.
2008 Jan 24
Strategies for prostate cancer prevention: Review of the literature.
2008 Jul
Analysis of overall survival in patients with nonmetastatic castration-resistant prostate cancer treated with vaccine, nilutamide, and combination therapy.
2008 Jul 15
Antiandrogen withdrawal in castrate-refractory prostate cancer: a Southwest Oncology Group trial (SWOG 9426).
2008 Jun
Synthesis and structure-activity relationships of the first ferrocenyl-aryl-hydantoin derivatives of the nonsteroidal antiandrogen nilutamide.
2008 Mar 27
A dramatic, objective antiandrogen withdrawal response: case report and review of the literature.
2008 Nov 5
Watchful waiting beats androgen deprivation therapy in early prostate cancer.
2008 Nov 5
Testosterone recovery after prolonged androgen suppression in patients with prostate cancer.
2008 Oct
FAF-Drugs2: free ADME/tox filtering tool to assist drug discovery and chemical biology projects.
2008 Sep 24
Fasting and cancer treatment in humans: A case series report.
2009 Dec 31
Impact level of dihydrotestosterone on the hypothalamic-pituitary-leydig cell axis in men.
2009 Feb
Genotoxic and endocrine activities of bis(hydroxyphenyl)methane (bisphenol F) and its derivatives in the HepG2 cell line.
2009 Jan 8
Integrating statistical predictions and experimental verifications for enhancing protein-chemical interaction predictions in virtual screening.
2009 Jun
CYP17 blockade by abiraterone: further evidence for frequent continued hormone-dependence in castration-resistant prostate cancer.
2009 Mar 10
Efficacy of salvage radiotherapy plus 2-year androgen suppression for postradical prostatectomy patients with PSA relapse.
2009 Nov 15
Prospective study evaluating postoperative radiotherapy plus 2-year androgen suppression for post-radical prostatectomy patients with pathologic T3 disease and/or positive surgical margins.
2009 Oct 1
Hormonal therapy of prostate cancer.
2010
Androgen receptor-dependent activation of endothelial nitric oxide synthase in vascular endothelial cells: role of phosphatidylinositol 3-kinase/akt pathway.
2010 Apr
The evolutionary impact of androgen levels on prostate cancer in a multi-scale mathematical model.
2010 Apr 20
A randomized phase II trial of mitoxantrone, estramustine and vinorelbine or bcl-2 modulation with 13-cis retinoic acid, interferon and paclitaxel in patients with metastatic castrate-resistant prostate cancer: ECOG 3899.
2010 Feb 24
Growth inhibition of androgen-responsive prostate cancer cells with brefeldin A targeting cell cycle and androgen receptor.
2010 Jan 26
Maximal androgen blockade for advanced prostate cancer.
2010 Jan-Mar
Involvement of androgen receptor in nitric oxide production induced by icariin in human umbilical vein endothelial cells.
2010 Jun 3
Activity of antiandrogens against juvenile and adult Schistosoma mansoni in mice.
2010 Sep
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dosage is 300 mg once a day for 30 days, followed thereafter by 150 mg once a day. Nilutamide Tablets can be taken with or without food.
Route of Administration: Oral
In Vitro Use Guide
At concentrations expected in the human liver (110 uM), nilutamide inhibited hexobarbital hydroxylase, benzphetamine N-demethylase, benzo(a)pyrene hydroxylase and 7-ethoxycoumarin O-deethylase activities by 85, 40, 35 and 25%, respectively in human liver microsomes.
Name Type Language
NILUTAMIDE
EP   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
NILUTAMIDE [EP]
Common Name English
NILUTAMIDE [INN]
Common Name English
NILUTAMIDE [ORANGE BOOK]
Common Name English
5,5-DIMETHYL-3-(.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-4-NITRO-M-TOLYL)HYDANTOIN
Systematic Name English
2,4-IMIDAZOLIDINEDIONE, 5,5-DIMETHYL-3-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-
Systematic Name English
NILUTAMIDE [MI]
Common Name English
RU 23908
Code English
NILUTAMIDE [MART.]
Common Name English
NILUTAMIDE [VANDF]
Common Name English
RU-23908
Code English
NILANDRON
Brand Name English
NILUTAMIDE [USAN]
Common Name English
NILUTAMIDE [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 686
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
NDF-RT N0000000243
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
NCI_THESAURUS C146993
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
WHO-VATC QL02BB02
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
WHO-ATC L02BB02
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
NDF-RT N0000175560
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
Code System Code Type Description
EPA CompTox
63612-50-0
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
MESH
C021277
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
NCI_THESAURUS
C1173
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
WIKIPEDIA
NILUTAMIDE
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
PUBCHEM
4493
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
MERCK INDEX
M7899
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1274
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
EVMPD
SUB09291MIG
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
DRUG BANK
DB00665
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
CAS
63612-50-0
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
INN
5755
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
IUPHAR
2864
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY
RXCUI
31805
Created by admin on Tue Oct 22 00:20:40 UTC 2019 , Edited by admin on Tue Oct 22 00:20:40 UTC 2019
PRIMARY RxNorm