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Apalutamide

Apalutamide structure

CAS No:
956104-40-8
Formula:
C21H15F4N5O2S
Chemical Name:
Apalutamide
Synonyms:
Benzamide,4-[7-[6-cyano-5-(trifluoromethyl)-3-pyridinyl]-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-2-fluoro-N-methyl-;4-[7-[6-Cyano-5-(trifluoromethyl)-3-pyridinyl]-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-2-fluoro-N-methylbenzamide;4-[7-[6-Cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide;ARN 509;A 52;Apalutamide;AR 509;Erleada;1361232-32-7
Categories:
Biochemical Engineering > Inhibitors

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Description

Apalutamide (ARN-509) is a potent and competitive androgen receptor (AR) antagonist, binding AR with an IC50 of 16 nM.

Apalutamide Basic Attributes

Molecular Weight：

477.4347128

Exact Mass：

477.43

EC Number：

-0

Characteristics

PSA：

121

XLogP3：

Density：

1.6±0.1 g/cm3

Refractive Index：

1.659

Safety Information

Precautionary statement(s)：

P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, P501

Hazard Statements：

H302

Apalutamide Use and Manufacturing

Coupling of A and B to produce 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5, 7-diazaspiro[3, 4]octan-5-yl)-2-fluoro-N-methylbenzamide, A52 5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile, 9, A is reacted with 4-(1-cyanocyclobutylamino)-2-fluoro-N-methylbenzamide B in DMF solution by heating in a microwave at 80° C. for 20 hours. Methanol and hydrochloric acid are then added and the reaction allowed to proceed for 2 hours to produce 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5, 7-diazaspiro[3.4]octan-5-yl)-2-fluoro-N-methylbenzamide, A52 (yield 35 to 87percent).amixture of A12 (0.03g, 0.13mmol) and B2 (0.032g, 0.13mmol) in DMF (0.5ml), under microwave irradiation, was heated at 80 for 20 hours. To this mixture, methanol (2 ml) and 2N HCl water (1ml) wereadded. Thissecond mixture was refluxed for 2 hours. After cooling to room temperature, thereaction mixture was poured into cold water (10 ml), and extracted with ethylacetate (15ml). The organic layer was dried over MgSO4, concentratedand was subjected to chromatography (dichloromethane: acetone, 95: 5) and A52(0.022g, 0.046mmol, 35percent) was obtained as a white powder

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