Chemical Properties of Anastrozole

The Anastrozole, with the CAS registry number 120511-73-1,  belongs to the product categories of Active Pharmaceutical Ingredients; Antineoplastic; All Inhibitors; Anti-neoplastic; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Anastrozole. This chemical’s molecular formula is C17H19N5 and molecular weight is 293.37. What’s more, its systematic name is 2,2′-[5-(1H-1,2,4-Triazol-1-ylmethyl)-1,3-phenylene]bis(2-methylpropanenitrile).

1. Application
Anastrozole (marketed under the trade name Arimidex by AstraZeneca) is a non-steroidal aromatase-inhibiting drug approved for treatment of breast cancer after surgery, as well as for metastasis in both pre and post-menopausal women. The severity of breast cancer can be increased by estrogen, as sex hormones cause hyperplasia, and differentiation at estrogen receptor sites. as well as for metastasis in both pre and post-menopausal women. It is an aromatase inhibitor and it is ued as an antineoplastic.
2. Classification codes
Its classification codes are: (1)Antineoplastic; (2)Antineoplastic Agents; (3)Antineoplastic agents, hormonal; (4)Aromatase Inhibitors; (5)Drug / Therapeutic Agent; (6)Enzyme inhibitors.
3. Physical properties
Name:Anastrozole

Molecular Formula:C17H19N5

CAS Registry Number:120511-73-1 

InChI:InChI=1/C17H19N5/c1-16(2,9-18)14-5-13(8-22-12-20-11-21-22)6-15(7-14)17(3,4)10-19/h5-7,11-12H,8H2,1-4H3

Appearance:crystalline solid

Molecular Weight:293.37

Density:1.08 g/cm3

Boiling Point:469.7 oC at 760 mmHg

Melting Point:81-82℃

Flash Point:469.7 oC at 760 mmHg

Storage Temperature:Store in original container in a cool dark place.

Refractive index:1.791

Solubility:Insoluble

Biological Activity:Potent and highly selective aromatase (CYP19) inhibitor (IC 50 = 15nM) that has no discernible effect on adrenocorticoid hormone synthesis. Reduces plasma estrogen levels and exhibits antitumor activity in vivo . Orally active.

Usage:An aromatase inhibitor. Used as an antineoplastic.
4. Chemical synthesis
The synthesis begins with nucleophilic substitution of two benzylic bromides in α,α’-dibromomesitylene (prepared by radical bromination of mesitylene, not shown on the scheme) with cyanide by treatment with potassium cyanide under phase transfer conditions, affording the dinitrile. Exhaustive methylation with methyl iodide and sodium hydride leads to the replacement of the more acidic side chain hydrogen atoms by methyl groups. The treatment with bromine in the presence of benzoyl peroxide leads to the formation of the corresponding benzyl bromide. Reaction of that product with 1,2,4-triazole in the presence of a base completes the synthesis of the aromatase inhibitor.
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