nilutamide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
non-steroid antiandrogens 1933 63612-50-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nilutamide
  • nilandrone
  • anandron
  • nilandron
Nilutamide ia a nonsteroidal, orally active antiandrogen. Nilutamide has demonstrated antiandrogenic activity without other hormonal (estrogen, progesterone, mineralocorticoid, and glucocorticoid) effects. In vitro, nilutamide blocks the effects of testosterone at the androgen receptor level. In vivo, nilutamide interacts with the androgen receptor and prevents the normal androgenic response.
  • Molecular weight: 317.22
  • Formula: C12H10F3N3O4
  • CLOGP: 1.71
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 1
  • TPSA: 92.55
  • ALOGS: -4.88
  • ROTB: 3
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 13.51 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 2.216 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.647 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 75.683 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 2.897 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 17.450 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 52.300 % High 1
herg hERG pIC50 4.353 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.626 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.126 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 19.560 % High 1
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,ITK,JAK2,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MARK4,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIM2,PLK1,PRKDC,STK33,SYK,TEK,TTK 39
kinase-selectivity-class AXL,GRK2,MAP2K6,MAPK7,STK33,TEK,TTK 7
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 2.360 High 1
mh-clint Mouse hepatocyte intrinsic clearance 2.208 High 1
mppb Mouse plasma protein binding (% unbound) 14.210 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.716 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 1
pppb Pig plasma protein binding (% unbound) 24.240 % High 1
rh-clint Rat hepatocyte intrinsic clearance 1.052 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 71.290 % High 1
rppb Rat plasma protein binding (% unbound) 17.480 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 161.065 uM High 1

Approvals:

DateAgencyCompanyOrphan
Sept. 19, 1996 FDA CONCORDIA PHARMS INC

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC L02BB02 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ENDOCRINE THERAPY
HORMONE ANTAGONISTS AND RELATED AGENTS
Anti-androgens
FDA MoA N0000000243 Androgen Receptor Antagonists
FDA EPC N0000175560 Androgen Receptor Inhibitor
MeSH PA D000726 Androgen Antagonists
MeSH PA D000970 Antineoplastic Agents
MeSH PA D006727 Hormone Antagonists
CHEBI has role CHEBI:35497 androgen antagonist
CHEBI has role CHEBI:35610 antineoplastic agent

Related Drugs by ATC class:

L02BB Anti-androgens 5 drugs
apalutamidebicalutamidedarolutamideenzalutamideflutamide

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Metastatic Prostate Carcinoma indication
Advanced Prostatic Carcinoma off-label use
Disorder of lung contraindication 19829001 DOID:850
Hepatic failure contraindication 59927004
Interstitial pneumonia contraindication 64667001
Decreased respiratory function contraindication 80954004
Incomplete Testicular Development contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.81 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Androgen receptor Nuclear hormone receptor ANTAGONIST IC50 8.05 CHEMBL CHEMBL

External reference:

IDSource
4021023 VUID
N0000148490 NUI
D00965 KEGG_DRUG
4021023 VANDF
C0068771 UMLSCUI
CHEBI:7573 CHEBI
CHEMBL1274 ChEMBL_ID
DB00665 DRUGBANK_ID
C021277 MESH_SUPPLEMENTAL_RECORD_UI
4493 PUBCHEM_CID
2864 IUPHAR_LIGAND_ID
5755 INN_ID
51G6I8B902 UNII
218741 RXNORM
13961 MMSL
399985 MMSL
5176 MMSL
6061 MMSL
d03831 MMSL
004198 NDDF
404866003 SNOMEDCT_US
96372005 SNOMEDCT_US
51G6I8B902 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nilutamide HUMAN PRESCRIPTION DRUG LABEL 1 62559-173 TABLET 150 mg ORAL ANDA 18 sections