Nilutamide

HCID 4493CAS 63612-50-0

Basic information

Standard SMILES
CC1(C)NC(=O)N(c2ccc([N+](=O)[O-])c(C(F)(F)F)c2)C1=O
InChIKey
XWXYUMMDTVBTOU-UHFFFAOYSA-N
Molecular formula
C12H10F3N3O4
Average molar mass
317.22 g/mol
Monoisotopic mass
317.06234046

Overview

Nilutamide is a C-nitro compound, an imidazolidinone and a member of (trifluoromethyl)benzenes. It has a role as an androgen antagonist and an antineoplastic agent.

Names & identifiers

Preferred name
Nilutamide
IUPAC
5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
English name
Nilutamide
Molecular formula
C12H10F3N3O4
Molecular weight
317.22

Names & synonyms

nilutamide63612-50-0AnandronNilandron5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)imidazolidine-2,4-dioneNilutamidaNilutamidum5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dioneRU-23908RU 239085,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoinDTXSID3034165
Show more names
NerumetNilandroneRU 23908-10Nilutamide CRSNilutamide USP/EP/BP
NSC-75868351G6I8B9025,5-Dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)-2,4-imidazolidinedione2,4-IMIDAZOLIDINEDIONE, 5,5-DIMETHYL-3-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-CHEBI:7573DTXCID10141655,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedioneAnadron

Database identifiers

CAS
63612-50-0
PubChem CID
4493
DTXSID
DTXSID3034165
ChEMBL
CHEMBL1274
ChEBI
CHEBI:7573
UNII
51G6I8B902
EC Number
624-700-6
Nikkaji
J33.120A

Properties

Computed structural properties

XLogP
2
Topological polar surface area
95.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
1
Heavy atoms
22

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents

Pharmaceuticals -> Listed in ZINC15

LogP1.8
Solubility4.19e-03 g/L
Human Drugs · 3 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Hormones and antihormones

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

Physicochemical properties

Melting point
1490 C · 1490C
Density
1.463 · 1.463±0.06 g/cm3(Predicted)
storage temp.
Sealed in dry,Room Temperature
solubility
Very slightly soluble in water, freely soluble in acetone, soluble in anhydrous ethanol.
form
solid
pka
7.59 · 7.59±0.70(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Hepatotoxicity · 1 item

In large registration clinical trials, ALT elevations occurred in 8% (range 2% to 33%) of patients during nilutamide therapy. The elevations were usually mild, asymptomatic and transient, requiring drug discontinuation in only 1% of treated patients. In rare instances, clinically apparent acute liver injury has occurred during nilutamide therapy, but the number of published cases are few, and the agent appears to be less hepatotoxic than flutamide. Nevertheless, fatal cases have been reported (Case 1). In reported cases, the latency to onset averaged 2 to 4 months and the clinical pattern of enzyme elevations was typically hepatocellular, thus largely resembling flutamide induced liver injury. Signs of hypersensitivity and autoimmunity were not common.

Exposure RoutesRapidly and completely absorbed, yielding high and persistent plasma concentrations.
Toxicity Summary · 1 item

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.

Signs and SymptomsSymptoms of overdose include dizziness, general discomfort, headache, nausea, and vomiting.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Nilutamide

vMost-DILI-concern

8

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
3
rtecs
NI9453300
ridadr
UN 2811 6.1/PG 3
hs_code
2933210000
risk_code
60-25
Signal word
Danger

Chemistry & industry

Pharmacology

ATC Code · 2 items

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Pharmacodynamics · 1 item

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 · 1 item

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.

Biological Half-Life38.0-59.1 hours
Metabolism/Metabolites · 2 items

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.

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

FDA Pharmacological Classification · 6 items

51G6I8B902

NILUTAMIDE

Mechanisms of Action [MoA] - Androgen Receptor Antagonists

Established Pharmacologic Class [EPC] - Androgen Receptor Inhibitor

Nilutamide is an Androgen Receptor Inhibitor. The mechanism of action of nilutamide is as an Androgen Receptor Antagonist.

NILUTAMIDE

Uses & manufacturing

UsesFor use in combination with surgical castration for the treatment of metastatic prostate cancer involving distant lymph nodes, bone, or visceral organs (Stage D2).
Applications · 4 items

DescriptionNilutamide is a non-steroidal anti-androgen similar in potency to the acyclic urea flutamide (55) and useful in the management of prostatic carcinoma.

HistoryThe second nonsteroidal anti-androgen to be marketed was nilutamide. It was discovered from a series of flutamide analogues at Roussel Uclaf (now Sanofi) in the 1970s using a rat prostate assay determining the inhibition of androgen uptake.The investigational compound code was RU 23908. Its structure is closely related to hydroxyflutamide, particularly under the assumption that the α-hydroxyamide engages in an internal hydrogen bond when bound to the AR LBD. The hydantoin moiety of nilutamide mimics the active conformation of hydroxyflutamide. Like flutamide, nilutamide blocks the action of androgens originating from both testis and adrenal. It also has neither agonist nor any other hormonal activity. Nilutamide has an elimination half-life of approximately 2 days in patients, which is significantly longer than that of flutamide. Thus, a single oral dose of 150 mg daily was feasible.

UsesNonsteroidal antiandrogen. Antineoplastic (hormonal)

General DescriptionNilutamide, 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-imidazolidinedione, is usedin combination with surgical castration for the treatment ofmetastatic prostate cancer. Nilutamide, which has an eliminationhalf-life of approximately 40 hours, can also be usedin once-daily dosing, but it has side effects that limit itsuse—visual disturbances, alcohol intolerance, and allergicpneumonitis.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
合肥曼奇诺生物医药技术有限公司19719236623 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]

Additional notes

DefinitionChEBI: Nilutamide is an imidazolidinone, a member of (trifluoromethyl)benzenes and a C-nitro compound. It has a role as an antineoplastic agent and an androgen antagonist.

Related reactions

25 records

Linked notes

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