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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

Molecular Formula C12H10F3N3O4
Molecular Weight 317.2207
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
New therapeutic targets in the treatment of prostate cancer.
2007 Jan
Fasting and cancer treatment in humans: A case series report.
2009 Dec 31
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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:20:40 UTC 2019
Edited
by admin
on Tue Oct 22 00:20:40 UTC 2019
Record UNII
51G6I8B902
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ACTIVE MOIETY