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Details

Stereochemistry ACHIRAL
Molecular Formula C12H10F3N3O4
Molecular Weight 317.2207
Optical Activity NONE
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
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

Primary TargetPharmacologyConditionPotency
9.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NILANDRON

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 mg/L
0.3 g single, oral
NILUTAMIDE plasma
Homo sapiens
2.3 mg/L
0.3 g single, oral
NILUTAMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
84 mg × h/L
0.3 g single, oral
NILUTAMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
56 h
0.3 g single, oral
NILUTAMIDE plasma
Homo sapiens
49 h
0.3 g single, oral
NILUTAMIDE plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
51G6I8B902
Record Status Validated (UNII)
Record Version