text.skipToContent text.skipToNavigation
Bulk Order
If not, click 'cancel'. You can also save this item for later.
Cancel
If not, click 'cancel'. You can also save this item for later.
Cancel

Mikromol feature product: Bicalutamide

no image

 

 

 Featured Product

 

Bicalutamide

 

API

 

Product Code: MM0894.00-0250

 

 

Introduction

 

Bicalutamide was first discovered in the 1980s and patented in 1982. It is a type of hormonal drug known as a non-steroidal antiandrogen (NSAA) and is used primarily to treat metastatic prostate cancer, but also prescribed for excessive hair growth or scalp hair loss in women, as well as early puberty and priapism in males. In 1995, AstraZeneca gained approval to market bicalutamide in the UK and US, and it is now on the World Health Organisation’s Model List of Essential Medicines and sold in more than 80 countries.


Mechanism of action

 

Antiandrogens work by blocking the androgen receptor and/or inhibiting or suppressing androgen production. Bicalutamide competes with androgen to bind to androgen receptors, consequently blocking the action of adrenal and testicular androgens that stimulate the growth of normal and malignant prostatic tissue. Blocking the effects of androgens helps stop the growth and spread of cancer cells.

 

Derived from structural modification of flutamide, bicalutamide was originally synthesised as a bacteriostatic agent in 1967 at Schering Plough Corporation and subsequently found to possess antiandrogenic activity. The "bica-" prefix corresponds to the fact that bicalutamide is a bicyclic compound, while "lutamide" is the standard suffix for NSAAs. Bicalutamide is comprised of a racemic mixture of the (R)-bicalutamide and (S)-bicalutamide enantiomers (these standards are also available in the Mikromol portfolio: MM0894.25-0025 and MM0894.26-0025).

 

 

Common synthesis

 

no image

 

 

 

Product Code

Product Name

 

Degradation product

MM0894.11-0025

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-oxirane-2-carboxamide

Impurity

Intermediate

MM0894.03-0025

Imp. B (EP): (2RS)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(2-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide

Impurity

 

MM0894.04-0025

Imp. C (EP): (2RS)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-methylpropanamide (Dehydroxybicalutamide)

Impurity

 

MM0894.25-0025

(R)-Bicalutamide

API component

 

MM0894.26-0025

(S)-Bicalutamide

API component

 

MM0894.18-0025

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylprop-2-enamide

Impurity

Intermediate

MM0894.20-0025

4-Amino-3-(trifluoromethyl)benzonitrile

Impurity

 

MM0894.08-0025

(RS)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(3-fluorophenylsulfonyl)-2-hydroxy-2-methylpropanamide

Impurity

 

MM0894.01-0025

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfinyl]-2-hydroxy-2-methylpropanamide

Impurity

 

MM0894.05-0025

Imp. D (EP): 4-Amino-2-(trifluoromethyl)benzonitrile

Impurity

Intermediate

MM0894.12-0025

Imp. J (EP): (2RS)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide

Impurity

Intermediate

MM0894.11-0025

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-oxirane-2-carboxamide

Impurity

Intermediate

Punchout session timeout warning

Your punchout session will expire in1 min59 sec.

Select "Continue session" to extend your session.