NILUTAMIDE

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Search structure


Trade Names	NILANDRON NILUTAMIDE
Synonyms	Anadron NSC-758683 Nilandron Nilutamide RU 23908 RU-23908
Status
Molecule Category	UNKNOWN
ATC	L02BB02
UNII	51G6I8B902
EPA CompTox	DTXSID3034165


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	XWXYUMMDTVBTOU-UHFFFAOYSA-N
Smiles	CC1(C)NC(=O)N(c2ccc([N+](=O)[O-])c(C(F)(F)F)c2)C1=O
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)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C12H10F3N3O4
Molecular Weight	317.22
AlogP	2.45
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	2.0
Polar Surface Area	92.55
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	22.0

Bioactivity

Mechanism of Action	Action	Reference
Androgen Receptor antagonist	ANTAGONIST	DailyMed


Protein: Androgen Receptor Description: Androgen receptor Organism : Homo sapiens P10275 ENSG00000169083

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	-	-	-	98
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4	-	9-600	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	117

Assay Description	Organism	Bioactivity	Reference
Inhibition of 1.0 nM [3H]mibolerone binding to human androgen receptor of PC3/AR cell lysate	Homo sapiens	9.0 nM
Inhibition of [3H]mibolerone binding to human Androgen receptor of PC3/AR Cell Lysate	Homo sapiens	9.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	116.58 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	97.83 %
Inhibition of COX-2 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control	Homo sapiens	98.0 %
Inhibition of COX-1 (unknown origin) using arachidonic acid as substrate assessed as formation of prostanoid products at 500 uM preincubated for 10 mins prior to substrate addition measured after 2 mins by Ellman's method relative to control	Homo sapiens	99.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	49.08 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	7.801 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.13 %
Inhibition of wild-type androgen receptor in human LAPC4 cells assessed as inhibition of DHT-induced luciferase activity measured after 24 hrs by luciferase reporter assay	Homo sapiens	600.0 nM

Cross References

Resources	Reference
ChEBI	7573
ChEMBL	CHEMBL1274
DrugBank	DB00665
DrugCentral	1933
FDA SRS	51G6I8B902
Human Metabolome Database	HMDB0014803
Guide to Pharmacology	2864
KEGG	C08164
PharmGKB	PA450632
PubChem	4493
SureChEMBL	SCHEMBL12670
ZINC	ZINC000003874498

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).