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
Show more names
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
- Formal charge
- 0
- Complexity
- 515
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antineoplastic and immunomodulating agents -> Antineoplastic agents
Pharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Hormones and antihormones
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)
- color
- Light yellow to yellow
- Major Application
- pharmaceutical (small molecule)
- 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)
- InChIKey
- XWXYUMMDTVBTOU-UHFFFAOYSA-N
- SMILES
- C1(=O)NC(C)(C)C(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1
- CAS DataBase Reference
- 63612 · 63612-50-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- Nilandron; nilutamide
- FDA UNII
- 51 G6I8B902 · 51G6I8B902
- NCI Drug Dictionary
- Nilandron
- ATC code
- 2 BB02 · L02BB02
- UNSPSC Code
- 51111800 · 51111800
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 301 · H301-H360
- Precautionary statements
- 201 · P201-P301+P310+P330
- Hazard Codes
- T
- Risk Statements
- 60 · 60-25
- Safety Statements
- 53 · 53-36/37/39-45
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 9453300 · NI9453300
- HazardClass
- 6.1 · 6.1
- HS Code
- 2933210000 · 2933210000
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 OralRepr · Acute Tox. 3 OralRepr. 1B
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Hepatotoxicity
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.
Toxicity Summary
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.
Drug Induced Liver Injury
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
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T
- safety_code
- 53-36/37/39-45
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301-H360
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 3 OralRepr. 1B
- Precautionary statements
- P201-P301+P310+P330
Chemistry & industry
Pharmacology
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Pharmacodynamics
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
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.
Metabolism/Metabolites
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
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
MeSH Pharmacological Classification
Compounds which inhibit or antagonize the biosynthesis or actions of androgens.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Absorption, Distribution and Excretion
Rapidly and completely absorbed, yielding high and persistent plasma concentrations.
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.
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
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
Linked notes
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