Nilutamide

Base Information

• Chemical Name: Nilutamide
• CAS No.: 63612-50-0
• Molecular Formula: C12H10F3N3O4
• Molecular Weight: 317.224
• Hs Code.: 2933210000
• European Community (EC) Number: 624-700-6
• NSC Number: 758683
• UNII: 51G6I8B902
• DSSTox Substance ID: DTXSID3034165
• Nikkaji Number: J33.120A
• Wikipedia: Nilutamide
• Wikidata: Q3877030
• NCI Thesaurus Code: C1173
• RXCUI: 31805
• Pharos Ligand ID: HFLGFZQ5J3P2
• Metabolomics Workbench ID: 42982
• ChEMBL ID: CHEMBL1274
• Mol file: 63612-50-0.mol

Synonyms:5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedione;Anandron;Nilandron;nilutamide;RU 23908;RU 23908-10;RU-23908

Chemical Property of Nilutamide

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 149 °C
• PKA: 7.59±0.70(Predicted)
• PSA: 95.23000
• Density: 1.463 g/cm³
• LogP: 3.36540
• Storage Temp.: Store at RT
• Solubility.: Very slightly soluble in water, freely soluble in acetone, soluble in anhydrous ethanol.
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 317.06234029
• Heavy Atom Count: 22
• Complexity: 515

Purity/Quality:

99.9% ^*data from raw suppliers

Nilutamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-25
• Safety Statements: 53-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C
• Recent ClinicalTrials: Standard Systemic Therapy With or Without Definitive Treatment in Treating Participants With Metastatic Prostate Cancer
• Recent EU Clinical Trials: Essai randomisé de phase III comparant l’association traitement hormonal + docétaxel au traitement hormonal seul dans les cancers de la prostate métastatiques
• Description: Nilutamide is a non-steroidal anti-androgen similar in potency to the acyclic urea flutamide (55) and useful in the management of prostatic carcinoma.
• Indications: Clinical trials with nilutamide were conducted predominantly in combination with orchiectomy. Results indicated retardation of disease progression and relief of metastatic bone pain in patientswith advanced prostate cancer.However, patient survival benefit was small compared with castration alone. Studies of nilutamide monotherapy or combination with LHRH agonists did not have sufficient patient numbers to allow reliable conclusions on efficacy. Nilutamide was first launched in France in 1987 for treatment of metastatic prostate cancer in adjuvant therapy with surgical castration. Approval in several major markets was granted in the following years. The tolerability profile of nilutamide was similar to that of flutamide. Hot flushes, nausea, diarrhea, constipation, gastrointestinal pain, abnormal liver function, and gynecomastia were frequently reported adverse events with both drugs. Additional side effects were predominantly associated with nilutamide treatment: interstitial pneumonitis, impaired adaptation to darkness, and alcohol intolerance. The nonsteroidal anti-androgens flutamide and nilutamide established combined androgen blockade as first-line treatment for metastatic prostate cancer. Still, there was room for improvement with regard to overall survival (OS) and tolerability.
• Clinical Use: Nilutamide is a hepatotoxic nitroaromatic antiandrogen used for the treatment of metastatic prostate carcinoma in men.

Technology Process of Nilutamide

There total 3 articles about Nilutamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-Fluoro-5-nitrobenzotrifluoride (400-74-8) + 5,5-dimethyl(trimethylsilyl)hydantoin (1245322-30-8) → nilutamide (63612-50-0)

Guidance literature:

2-Fluoro-5-nitrobenzotrifluoride; With cesium fluoride; In N,N-dimethyl-formamide; for 0.166667h; Inert atmosphere;

5,5-dimethyl(trimethylsilyl)hydantoin; In N,N-dimethyl-formamide; at 60 ℃; for 16h;

Reference yield:

5,5-dimethyl-imidazolidine-2,4-dione (77-71-4) + 4-fluoro-1-nitro-2-trifluoromethyl-benzene (393-09-9) → nilutamide (63612-50-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 7h; Inert atmosphere;

Reference yield:

→ nilutamide (63612-50-0)

Guidance literature:

Entspr. Iminoimidazolin-2-on (Bsp. 1A), HCl;

upstream raw materials:

2-Fluoro-5-nitrobenzotrifluoride

5,5-dimethyl(trimethylsilyl)hydantoin

5,5-dimethyl-imidazolidine-2,4-dione

4-fluoro-1-nitro-2-trifluoromethyl-benzene

Downstream raw materials:

1,1'-butane-1,4-diylbis{5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)-phenyl]imidazolidine-2,4-dione}

5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-1-{5-[(4,4,5,5,5-pentafluoropentyl)thio]pentyl}imidazolidine-2,4-dione

5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-1-{9-[S-(4,4,5,5,5-pentafluoropentyl)sulphonimidoyl]nonyl}imidazolidine-2,4-dione

N-[(9-{5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-2,4-dioxoimidazolidin-1-yl}nonyl)(oxido)(4,4,5,5,5-pentafluoropentyl)-λ4-sulphanylidene]-2,2,2-trifluoroacetamide

Refernces

• 1、 -. "METHOD FOR COUPLING HALOGEN-SUBSTITUTED AROMATIC COMPOUNDS WITH ORGANIC COMPOUNDS COMPRISING TRIALKYLSILYL-SUBSTITUTED HETEROATOMS". Page/Page column 7. . Retrieved 2012/06/16.