Identification
- Summary
Nilutamide is an antineoplastic hormone used to treat prostate cancer.
- Brand Names
- Anandron, Nilandron
- Generic Name
- Nilutamide
- DrugBank Accession Number
- DB00665
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Nilutamide (DB00665)
- Weight
- Average: 317.2207
Monoisotopic: 317.062340438 - Chemical Formula
- C12H10F3N3O4
- Synonyms
- 5,5-Dimethyl-3-(α,α,α-trifluoro-4-nitro-m-tolyl)hydantoin
- Nilutamida
- Nilutamide
- Nilutamidum
- External IDs
- RU 23908
- RU-23908
Pharmacology
- Indication
For use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in treatment of Metastatic prostate cancer •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
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.
- Mechanism of action
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.
Target Actions Organism AAndrogen receptor antagonistHumans - Absorption
Rapidly and completely absorbed, yielding high and persistent plasma concentrations.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
The results of a human metabolism study using 14C-radiolabelled tablets show that nilutamide is extensively metabolized and less than 2% of the drug is excreted unchanged in urine after 5 days.
- Route of elimination
Nilutamide is extensively metabolized andless than 2% of the drug is excreted unchanged in urine after 5 days. Fecal elimination is negligible, ranging from 1.4% to 7% of the dose after 4 to 5 days.
- Half-life
38.0-59.1 hours
- Clearance
Not Available
- Adverse Effects
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Symptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Nilutamide may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept The metabolism of Nilutamide can be increased when combined with Abatacept. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Nilutamide. Aceclofenac Aceclofenac may decrease the excretion rate of Nilutamide which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Nilutamide which could result in a higher serum level. - Food Interactions
- Avoid alcohol.
- Take separate from meals. Take before breakfast.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anandron Tablet 50 mg Oral Cheplapharm Arzneimittel Gmbh 1997-08-20 Not applicable Canada 
Anandron - Tab 100mg Tablet 100 mg Oral Aventis Pharma Ltd. 1997-08-20 2003-07-22 Canada Anandron Tab 100mg Tablet 100 mg / tab Oral Hoechst Roussel Canada Inc. 1992-12-31 1999-08-11 Canada Anandron Tab 100mg Tablet 100 mg / tab Oral Roussel Canada Inc. 1992-12-31 1996-09-09 Canada Anandron Tab 50mg Tablet 50 mg / tab Oral Hoechst Roussel Canada Inc. 1994-12-31 1999-08-11 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Nilutamide Tablet 150 mg/1 Oral CENEXI HSC 2019-11-22 Not applicable US 
Nilutamide Tablet 150 mg/1 Oral Prasco Laboratories 2019-11-22 Not applicable US Nilutamide Tablet 150 mg/1 Oral ANI Pharmaceuticals, Inc. 2016-07-18 Not applicable US
Categories
- ATC Codes
- L02BB02 — Nilutamide
- Drug Categories
- Androgen Receptor Antagonists
- Androgen Receptor Inhibitors
- Antiandrogens
- Antiandrogens, non-steroidal
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (weak)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Endocrine Therapy
- Hormone Antagonists
- Hormone Antagonists and Related Agents
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Imidazoles
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azolidines
- Sub Class
- Imidazolidines
- Direct Parent
- Phenylhydantoins
- Alternative Parents
- Phenylimidazolidines / Trifluoromethylbenzenes / Alpha amino acids and derivatives / Nitrobenzenes / Nitroaromatic compounds / N-acyl ureas / Dicarboximides / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organic oxoazanium compounds show 8 more
- Substituents
- 3-phenylhydantoin / Alkyl fluoride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / C-nitro compound / Carbonic acid derivative show 25 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- C-nitro compound, imidazolidinone, (trifluoromethyl)benzenes (CHEBI:7573)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 51G6I8B902
- CAS number
- 63612-50-0
- InChI Key
- XWXYUMMDTVBTOU-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
- SMILES
- CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F
References
- General References
- Kassouf W, Tanguay S, Aprikian AG: Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol. 2003 May;169(5):1742-4. [Article]
- Lukka H, Waldron T, Klotz L, Winquist E, Trachtenberg J: Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review. Curr Oncol. 2006 Jun;13(3):81-93. [Article]
- External Links
- Human Metabolome Database
- HMDB0014803
- KEGG Drug
- D00965
- KEGG Compound
- C08164
- PubChem Compound
- 4493
- PubChem Substance
- 46505381
- ChemSpider
- 4337
- BindingDB
- 50135912
- 31805
- ChEBI
- 7573
- ChEMBL
- CHEMBL1274
- ZINC
- ZINC000003874498
- Therapeutic Targets Database
- DAP000302
- PharmGKB
- PA450632
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Nilutamide
- FDA label
- Download (70.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Prostate Cancer 3 3 Recruiting Treatment Castration Levels of Testosterone / Metastatic Prostate Adenocarcinoma / Stage IV Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8 / Stage IVB Prostate Cancer AJCC v8 1 2 Active Not Recruiting Treatment Adenocarcinoma of Prostate / Recurrent Prostate Carcinoma 1 2 Completed Treatment Prostate Cancer 2 2 Terminated Treatment Prostate Cancer 1
Pharmacoeconomics
- Manufacturers
- Sanofi aventis us llc
- Packagers
- Sanofi-Aventis Inc.
- Dosage Forms
Form Route Strength Tablet Oral 50 mg Tablet Oral 100 mg Tablet Oral 100 mg / tab Tablet Oral 50 mg / tab Tablet Oral 150 mg/1 - Prices
Unit description Cost Unit Nilandron 150 mg tablet 18.03USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 1.8 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00419 mg/mL ALOGPS logP 1.74 ALOGPS logP 2.25 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 15.01 Chemaxon pKa (Strongest Basic) -4.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 92.55 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 67.22 m3·mol-1 Chemaxon Polarizability 25.92 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.8491 Caco-2 permeable - 0.5254 P-glycoprotein substrate Non-substrate 0.637 P-glycoprotein inhibitor I Non-inhibitor 0.8572 P-glycoprotein inhibitor II Non-inhibitor 0.9314 Renal organic cation transporter Non-inhibitor 0.9567 CYP450 2C9 substrate Non-substrate 0.7776 CYP450 2D6 substrate Non-substrate 0.8934 CYP450 3A4 substrate Non-substrate 0.527 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8293 Ames test AMES toxic 0.6671 Carcinogenicity Non-carcinogens 0.6032 Biodegradation Not ready biodegradable 0.9944 Rat acute toxicity 3.0768 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9684 hERG inhibition (predictor II) Non-inhibitor 0.8734
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a59-9051000000-b212093377487cffc158 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.9509716 predictedDarkChem Lite v0.1.0 [M-H]- 160.1407586 predictedDarkChem Lite v0.1.0 [M-H]- 166.05482 predictedDeepCCS 1.0 (2019) [M+H]+ 173.8413716 predictedDarkChem Lite v0.1.0 [M+H]+ 174.1338343 predictedDarkChem Lite v0.1.0 [M+H]+ 169.72453 predictedDeepCCS 1.0 (2019) [M+Na]+ 173.3218716 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.4806902 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.28984 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
References
- Raynaud JP: Antiandrogens in combination with LH-RH agonists in prostate cancer. Am J Clin Oncol. 1988;11 Suppl 2:S132-47. [Article]
- Moguilewsky M, Bertagna C, Hucher M: Pharmacological and clinical studies of the antiandrogen Anandron. J Steroid Biochem. 1987;27(4-6):871-5. [Article]
- Raynaud JP, Bonne C, Moguilewsky M, Lefebvre FA, Belanger A, Labrie F: The pure antiandrogen RU 23908 (Anandron), a candidate of choice for the combined antihormonal treatment of prostatic cancer: a review. Prostate. 1984;5(3):299-311. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Labrie F: Hormonal therapy of prostate cancer. Prog Brain Res. 2010;182:321-41. doi: 10.1016/S0079-6123(10)82014-X. [Article]
- Schasfoort EM, Van De Beek C, Newling DW: Safety and efficacy of a non-steroidal anti-androgen, based on results of a post marketing surveillance of nilutamide. Prostate Cancer Prostatic Dis. 2001;4(2):112-117. [Article]
- Kaisary AV, Iversen P, Tyrrell CJ, Carroll K, Morris T: Is there a role for antiandrogen monotherapy in patients with metastatic prostate cancer? Prostate Cancer Prostatic Dis. 2001;4(4):196-203. [Article]
- Kolvenbag GJ, Furr BJ, Blackledge GR: Receptor affinity and potency of non-steroidal antiandrogens: translation of preclinical findings into clinical activity. Prostate Cancer Prostatic Dis. 1998 Dec;1(6):307-314. [Article]
- Brawer MK, Crawford ED, Labrie F, Mendoza-Valdes A, Miller PD, Petrylak DP: Androgen deprivation and other treatments for advanced prostate cancer. Rev Urol. 2001;3 Suppl 2:S59-68. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Badowski ME, Burton B, Shaeer KM, Dicristofano J: Oral oncolytic and antiretroviral therapy administration: dose adjustments, drug interactions, and other considerations for clinical use. Drugs Context. 2019 Feb 13;8:212550. doi: 10.7573/dic.212550. eCollection 2019. [Article]
- Flockhart Table of Drug Interactions [Link]
- niLUTAmide - Cancer Care Ontario [Link]
- Nilutamide Monograph - BC Cancer [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
- Specific Function
- This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
- Gene Name
- POR
- Uniprot ID
- P16435
- Uniprot Name
- NADPH--cytochrome P450 reductase
- Molecular Weight
- 76689.12 Da
References
- Berger V, Berson A, Wolf C, Chachaty C, Fau D, Fromenty B, Pessayre D: Generation of free radicals during the reductive metabolism of nilutamide by lung microsomes: possible role in the development of lung lesions in patients treated with this anti-androgen. Biochem Pharmacol. 1992 Feb 4;43(3):654-7. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54