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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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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