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ChemicalBook > Product Catalog >Biochemical Engineering >Inhibitors >Endocrinology & Hormones >Androgen Receptor Antagonists >Enzalutamide

Enzalutamide

Enzalutamide Structure
CAS No.
915087-33-1
Chemical Name:
Enzalutamide
Synonyms
CS-355;101095;MDV-3100;Mr Amine;Ezalutamide;EnzalutaMide;Enzalutamide API;Enzalutamide, >=99%;brand name: Xtandi.;ENZALUTAMIDE;MDV-3100
CBNumber:
CB62500946
Molecular Formula:
C21H16F4N4O2S
Molecular Weight:
464.44
MOL File:
915087-33-1.mol
Modify Date:
2025/2/23 21:28:46
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Enzalutamide Properties

Melting point 198 - 200°C
Density 1.49
storage temp. -20°C
solubility Soluble in DMSO (>25 mg/ml)
form solid
pka 13.88±0.46(Predicted)
color White to off-white
Stability Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)
InChIKey WXCXUHSOUPDCQV-UHFFFAOYSA-N
SMILES C(NC)(=O)C1=CC=C(N2C(=S)N(C3=CC=C(C#N)C(C(F)(F)F)=C3)C(=O)C2(C)C)C=C1F

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H227
Precautionary statements  P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235
HS Code  29339900
NFPA 704
0
2 0

Enzalutamide Chemical Properties,Uses,Production

Description

In August 2012, the US FDA approved enzalutamide for the treatment of metastatic castration-resistant prostate cancer (mCRPC) in patients who have previously been treated with docetaxel. Synthesis of enzalutamide was achieved by a triply convergent route that employed a Strecker condensation, followed by isothiocyanate condensation and hydrolysis to form the thiohydantoin moiety. In LNCaP/AR cells with high expression of AR, enzalutamide demonstrated potent inhibition of 16b-[18F]-5α-dihydrotestosterone binding (IC50=21 nM compared with bicalutamide IC50=160 nM), and inhibited AR translocation to the nucleus more potently than bicalutamide.The primary metabolite is the result of CYP2C8-mediated N-demethylation; enzalutamide is primarily eliminated by hepatic metabolism.

Chemical Properties

White Solid

Uses

MDV3100, known as Enzalutamide, is a second-generation androgen receptor (AR) signaling inhibitor. It is able to inhibit binding of androgens to the AR, AR nuclear translocation, and the association of the AR with DNA.

Definition

ChEBI: A benzamide obtained by formal condensation of the carboxy group of 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl}-2-fluorobenzoic acid with methylamine. Used for the treatment of of metastatic castration-resistant p ostate cancer.

Clinical Use

In August 2012, the FDA approved enzalutamide, marketed by Medivation and Astellas Pharma US for the treatment of metastatic castration-resistant prostate cancer (CRPC), specifically for those patients who had previously received docetaxel. Enzalutamide is an inhibitor of androgen receptors (AR)— whose increased expression has been closely linked with castration-resistant prostate cancer (CRPC),thus, AR inhibitors have seen increased recent attention from the medicinal chemistry community. Phase I/II trials were particularly promising for enzalutamide, as 43% of patients showed >50% sustained suppression of a key serum biomarker.

Enzalutamide Preparation Products And Raw materials

Raw materials

4-(4,4-Dimethyl-5-oxo-2-thioxo-1-imidazolidinyl)-2-trifluoromethylbenzonitrile Propanoic acid,2-chloro-2-methyl-, methyl ester 4-Bromo-2-fluoro-N-methylbenzamide 4-isothiocyanato-2-(trifluoroMethyl)benzonitrile 4-(2-CYANOPROPAN-2-YLAMINO)-2-FLUORO-N-METHYLBENZAMIDE
N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester 4-[1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-1-methyl-ethylamino]-2-fluoro-N- N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine
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Preparation Products

Enzalutamide Suppliers

Global( 536)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
GLR Innovations +91 9891111994 New Delhi, India 4535 58 Inquiry
AVD pharmaceuticals Pvt Ltd +919860835260 Pune, India 102 58 Inquiry
Dr. Reddy's Laboratories Ltd +91-4049002900 +91-4049002900 Hyderabad, India 165 58 Inquiry
J S LABS +91-7330612784 +91-7330612784 Tamil Nadu, India 159 58 Inquiry
CDYMAX +91-9019317788 +91-9019317788 Bangalore, India 28 58 Inquiry
Gonane Pharma +91-9819380043 +91-9819380043 NaviMumbai, India 192 58 Inquiry
Shilpa Medicare Limited (SML) +91-8532238704 +91-9320649838 Karnataka, India 61 58 Inquiry
Crams Technologies 0129-4011068 New Delhi, India 39 58 Inquiry
Basil Drugs AND Pharmaceuticals Pvt Ltd +91-2249700250 +91-9619320820 Mumbai, India 108 58 Inquiry
Zydus Lifesciences Ltd. +91-0265-2315243 +91-6358895661 Gujarat, India 89 58 Inquiry
Supplier Advantage
GLR Innovations 58
AVD pharmaceuticals Pvt Ltd 58
Dr. Reddy's Laboratories Ltd 58
J S LABS 58
CDYMAX 58
Gonane Pharma 58
Shilpa Medicare Limited (SML) 58
Crams Technologies 58
Basil Drugs AND Pharmaceuticals Pvt Ltd 58
Zydus Lifesciences Ltd. 58

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4-{3-[4-cyano-3-(trifluoroMethyl)phenyl]-5,5-diMethyl-4-oxo-2-sulfanylideneiMidazolidin-1-yl}-2-fluoro-N-MethylbenzaMide EnzalutaMide MDV3100 (EnzalutaMide) ENZALUTAMIDE;MDV-3100 MDV-3100 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl]-2-fluoro-N-methylbenzamide 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide MDV 3100,4-[3-[4-Cyano-3-(trifluoroMethyl)phenyl]-5,5-diMethyl-4-oxo-2-thioxo-1-iMidazolidinyl]-2-fluoro-N-MethylbenzaMide 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N BenzaMide,4-[3-[4-cyano-3-(trifluoroMethyl)phenyl]-5,5-diMethyl-4-oxo-2-thioxo-1-iMidazolidinyl]-2-fluoro-N-Methyl- 4-[3-(4-Ethynyl-3-trifluoromethyl-phenyl)-5,5-dimethyl-4-oxo-2-thioxo-imidazolidin-1-yl]-2-fluoro-N-methyl-benzamide 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl]-2-fluoro-N-methylbenzamide MDV 3100 MDV3100,Menzalutamide Xtandi (enzalutamide) (androgen receptor inhibitor) 4-Thiazolecarboxylic acid, 2-[(2,4,5-trimethoxybenzoyl)amino]-ethyl ester Enzalutamide, >=99% 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluor brand name: Xtandi. MDV-3100; MDV 3100. ENZALUTAMIDE; BRAND NAME: XTANDI. CS-355 4-{3-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-5,5-DIMETHYL-4-OXO-2-SULFANYLIDENEIMIDAZOLIDIN-1-YL}-2-FLUO 101095 Enzalutamide (Xtandi) Ezalutamide 5-dimethyl-4-oxo-2-thioxoimid azolidin-1-yl)-2-fluoro-Nmethylbenzamide 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5 ENZALUTAMIDE 915087-33-1 MDV3100 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N(For export only) Enzalutamide USP/EP/BP 4-Isothiocyanato-2-trifluoromethylbenzonitrile, 4-Isothiocyanato-2-(trifluoromethyl)benzonitril 4-{3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-... EnzalutamideQ: What is Enzalutamide Q: What is the CAS Number of Enzalutamide Q: What is the storage condition of Enzalutamide Q: What are the applications of Enzalutamide Mr Amine Enzalutamide API 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide? (Enzalutamide Impurity) Enzalutamide, 10 mM in DMSO 915087-33-1 C21H16F4N4O2S Apoptosis Aromatics Heterocycles Inhibitors Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds Inhibitor 1 API 915087-33-1