Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H10F3N3O4 |
Molecular Weight | 317.2212 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)C(=O)N(c2ccc(c(c2)C(F)(F)F)N(=O)=O)C(=N1)O
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB00665Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00665
Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/207631Orig1s000lbl.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/385986
Curator's Comment:: Like flutamide and bicalutamide, nilutamide is able to cross the blood-brain-barrier and has central antiandrogen actions.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1871 Sources: http://www.drugbank.ca/drugs/DB00665 |
9.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | NILANDRON Approved UseMetastatic Prostate Cancer
Nilutamide Tablets are indicated for use in combination with surgical castration for the treatment
of metastatic prostate cancer (Stage D2). Launch Date8.4300477E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.3 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8453188 |
0.3 g single, oral dose: 0.3 g route of administration: Oral experiment type: SINGLE co-administered: |
NILUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.3 mg/L |
0.3 g single, oral dose: 0.3 g route of administration: Oral experiment type: SINGLE co-administered: |
NILUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
84 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8453188 |
0.3 g single, oral dose: 0.3 g route of administration: Oral experiment type: SINGLE co-administered: |
NILUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
49 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8453188 |
0.3 g single, oral dose: 0.3 g route of administration: Oral experiment type: SINGLE co-administered: |
NILUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
56 h |
0.3 g single, oral dose: 0.3 g route of administration: Oral experiment type: SINGLE co-administered: |
NILUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
DLT: Nausea, Vomiting... Disc. AE: Hot flashes, Interstitial lung disease... Dose limiting toxicities: Nausea (7.5%) AEs leading toVomiting (7.5%) discontinuation/dose reduction: Hot flashes (5.7%) Sources: Page: p.1075Interstitial lung disease (3.8%) Visual disturbance NOS (1.9%) Pruritus (1.9%) Dizziness (1.9%) Headache (1.9%) Hepatic enzyme increased (1.9%) |
13 g single, oral Overdose Dose: 13 g Route: oral Route: single Dose: 13 g Sources: |
unhealthy, 79 n = 1 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 79 Sex: M Population Size: 1 Sources: |
Disc. AE: Vomiting, Diarrhoea... AEs leading to discontinuation/dose reduction: Vomiting (moderate) Sources: Diarrhoea (moderate) |
900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 4 Sources: |
Disc. AE: Gastrointestinal disorders, Nausea... AEs leading to discontinuation/dose reduction: Gastrointestinal disorders Sources: Nausea Vomiting Malaise Headache Dizziness |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Co-administed with:: leuprolide Sources: Page: p.8 |
unhealthy n = 209 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 209 Sources: Page: p.8 |
Disc. AE: Visual disturbances... AEs leading to discontinuation/dose reduction: Visual disturbances (1 - 2) Sources: Page: p.8 |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Sources: Page: p.3 |
Disc. AE: Interstitial pneumonitis, Pulmonary fibrosis... AEs leading to discontinuation/dose reduction: Interstitial pneumonitis (2%) Sources: Page: p.3Pulmonary fibrosis (grade 5, rare) |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Sources: Page: p.4 |
Disc. AE: Liver injury... AEs leading to discontinuation/dose reduction: Liver injury (severe, rare) Sources: Page: p.4 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | 1.9% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Headache | 1.9% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Hepatic enzyme increased | 1.9% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Pruritus | 1.9% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Visual disturbance NOS | 1.9% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Interstitial lung disease | 3.8% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Hot flashes | 5.7% Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Nausea | 7.5% DLT |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Vomiting | 7.5% DLT |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: Page: p.1075 |
unhealthy, 47-93 n = 53 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 47-93 Sex: M Population Size: 53 Sources: Page: p.1075 |
Diarrhoea | moderate Disc. AE |
13 g single, oral Overdose Dose: 13 g Route: oral Route: single Dose: 13 g Sources: |
unhealthy, 79 n = 1 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 79 Sex: M Population Size: 1 Sources: |
Vomiting | moderate Disc. AE |
13 g single, oral Overdose Dose: 13 g Route: oral Route: single Dose: 13 g Sources: |
unhealthy, 79 n = 1 Health Status: unhealthy Condition: Metastatic prostate cancer Age Group: 79 Sex: M Population Size: 1 Sources: |
Dizziness | Disc. AE | 900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 4 Sources: |
Gastrointestinal disorders | Disc. AE | 900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 4 Sources: |
Headache | Disc. AE | 900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 4 Sources: |
Malaise | Disc. AE | 900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 4 Sources: |
Nausea | Disc. AE | 900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 4 Sources: |
Vomiting | Disc. AE | 900 mg 1 times / day multiple, oral Highest studied dose Dose: 900 mg, 1 times / day Route: oral Route: multiple Dose: 900 mg, 1 times / day Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 4 Sources: |
Visual disturbances | 1 - 2 Disc. AE |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Co-administed with:: leuprolide Sources: Page: p.8 |
unhealthy n = 209 Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Population Size: 209 Sources: Page: p.8 |
Interstitial pneumonitis | 2% Disc. AE |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Sources: Page: p.3 |
Pulmonary fibrosis | grade 5, rare Disc. AE |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Sources: Page: p.3 |
Liver injury | severe, rare Disc. AE |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Metastatic prostate cancer Sex: M Sources: Page: p.4 |
PubMed
Title | Date | PubMed |
---|---|---|
Flare Associated with LHRH-Agonist Therapy. | 2001 |
|
Androgen deprivation and other treatments for advanced prostate cancer. | 2001 |
|
Therapeutic androgen receptor ligands. | 2003 |
|
Major impact of hormonal therapy in localized prostate cancer--death can already be an exception. | 2004 Dec |
|
Steroid activities comparison of natural and food wrap compounds in human breast cancer cell lines. | 2004 Jun |
|
Vaccine therapy for a patient with androgen-insensitive prostate cancer without evidence of measurable disease on scans. | 2004 May-Jun |
|
Monotherapy in advanced prostate cancer: an overview. | 2004 Sep |
|
Intermittent androgen deprivation for biologic recurrence after radical prostatectomy: long-term experience. | 2005 Apr |
|
Antiandrogen, vaccine and combination therapy in patients with nonmetastatic hormone refractory prostate cancer. | 2005 Aug |
|
How are hemoglobin levels affected by androgen deprivation in non-metastatic prostate cancer patients? | 2005 Feb |
|
Three-dimensional structure-activity relationships of nonsteroidal ligands in complex with androgen receptor ligand-binding domain. | 2005 Feb 24 |
|
[From the finger to the eye!...]. | 2005 Jul |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Combined androgen blockade: the case for bicalutamide. | 2005 Mar |
|
Prolonged response to nilutamide in a patient with stage D0.5 prostate cancer who previously failed androgen deprivation therapy. | 2005 Mar-Apr |
|
Prostate cancer PET bioprobes: synthesis of [18F]-radiolabeled hydroxyflutamide derivatives. | 2005 Nov 15 |
|
Efficacy of nilutamide as secondary hormonal therapy in androgen-independent prostate cancer. | 2005 Oct |
|
Mitochondrial permeability transition as a source of superoxide anion induced by the nitroaromatic drug nimesulide in vitro. | 2005 Oct 1 |
|
Nontranscriptional regulation of cardiac repolarization currents by testosterone. | 2005 Sep 20 |
|
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 |
|
Metabolism of nilutamide in rat lung. | 2006 Jan 12 |
|
GREB1 is a novel androgen-regulated gene required for prostate cancer growth. | 2006 Jun 1 |
|
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 |
|
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 |
|
In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
|
Antiandrogenic activity of pyrethroid pesticides and their metabolite in reporter gene assay. | 2007 Jan |
|
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 |
|
Analysis of overall survival in patients with nonmetastatic castration-resistant prostate cancer treated with vaccine, nilutamide, and combination therapy. | 2008 Jul 15 |
|
Delayed dark adaptation caused by nilutamide. | 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 |
|
FAF-Drugs2: free ADME/tox filtering tool to assist drug discovery and chemical biology projects. | 2008 Sep 24 |
|
Fulminant hepatic failure due to nilutamide hepatotoxicity. | 2009 Apr |
|
Fasting and cancer treatment in humans: A case series report. | 2009 Dec 31 |
|
CYP17 blockade by abiraterone: further evidence for frequent continued hormone-dependence in castration-resistant prostate cancer. | 2009 Mar 10 |
|
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 |
|
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 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2930595
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.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
686
Created by
admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
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NDF-RT |
N0000000243
Created by
admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
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NCI_THESAURUS |
C146993
Created by
admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
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WHO-VATC |
QL02BB02
Created by
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WHO-ATC |
L02BB02
Created by
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NDF-RT |
N0000175560
Created by
admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
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Code System | Code | Type | Description | ||
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63612-50-0
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PRIMARY | |||
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C021277
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PRIMARY | |||
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C1173
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PRIMARY | |||
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NILUTAMIDE
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4493
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PRIMARY | |||
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M7899
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CHEMBL1274
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SUB09291MIG
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51G6I8B902
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DB00665
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1933
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63612-50-0
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5755
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1463472
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2864
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31805
Created by
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ACTIVE MOIETY