Anastrozole

Base Information

• Chemical Name: Anastrozole
• CAS No.: 120511-73-1
• Molecular Formula: C17H19N5
• Molecular Weight: 293.371
• Hs Code.: 29339980
• European Community (EC) Number: 601-715-6
• NSC Number: 759855,719344
• UNII: 2Z07MYW1AZ
• DSSTox Substance ID: DTXSID9022607
• Nikkaji Number: J592.428F
• Wikipedia: Anastrozole
• Wikidata: Q419143
• NCI Thesaurus Code: C1607
• RXCUI: 84857
• Pharos Ligand ID: K661VM6CHSU8
• Metabolomics Workbench ID: 43430
• ChEMBL ID: CHEMBL1399
• Mol file: 120511-73-1.mol

Synonyms:2,2'-(5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene)bis(2-methylpropionitrile);anastrazole;anastrozole;Arimidex;ICI D1033;ZD 1033;ZD-1033;ZD1033;Zeneca ZD 1033

Chemical Property of Anastrozole

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 81 - 82 °C
• Refractive Index: 1.791
• Boiling Point: 469.718 °C at 760 mmHg
• PKA: 2.62±0.10(Predicted)
• Flash Point: 237.877 °C
• PSA: 78.29000
• Density: 1.085 g/cm³
• LogP: 2.92876
• Storage Temp.: Store at RT
• Solubility.: DMSO: soluble40mg/mL
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 293.16404563
• Heavy Atom Count: 22
• Complexity: 456

Purity/Quality:

99% ^*data from raw suppliers

Anastrozole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-61-60
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CC(C)(C#N)C1=CC(=CC(=C1)CN2C=NC=N2)C(C)(C)C#N
• Recent ClinicalTrials: Anti-Hormone Therapy (With Anastrazole and Fulvestrant) Before Surgery to Treat Postmenopausal Women With Breast Cancer.
• Recent EU Clinical Trials: An Open-Label, Randomized, Non-Comparative Phase 2 Study of ARV-471 or Anastrozole in Post-Menopausal Women With ER+/HER2– Breast Cancer in the Neoadjuvant Setting
• Recent NIPH Clinical Trials: A Phase III, Double-blind, Randomised Study to Assess Switching to AZD9833 (a Next Generation, Oral SERD) + CDK4/6 Inhibitor (Palbociclib or Abemaciclib) vs Continuing Aromatase Inhibitor (Letrozole or Anastrozole)+ CDK4/6 Inhibitor in HR+/HER2-MBC Patients With Detectable ESR1Mutation Without Disease Progression During 1L Treatment With Aromatase Inhibitor+ CDK4/6 Inhibitor- A ctDNA Guided Early Switch Study
• Description: Anastrozole, chemically known as 2,2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]bis(2-methylpropiononitrile) a derivative of benzotriazole with the CAS registry number 120511-73-1, is a non-steroidal, third-generation achiral triazole derivative marketed as ARIMIDEX? by AstraZeneca Pharmaceuticals LP1. It is one of the third-generation aromatase inhibitor which is a highly competitive and selective inhibitor of aromatase, thus blocking the conversion of testosterone into estradiol and androstenedione into estrone. Inhibition of the aromatase enzyme occurs particularly through competitive binding of aromatase to the hemegroup of cytochrome P450, decreasing estrogen biosynthesis in the peripheral tissues of the body and in the breast. Anastrozole entered its first market in the United Kingdom for the treatment of advanced breast cancer in post-menopausal women. Anastrozole is a highly potent and selective aromatase inhibitor. It is extremely potent in lowering circulating estradiol to undetectable levels in treated patients without altering other circulating hormones. The drug is reportedly well absorbed and tolerated following oral administration.
• Uses: Anastrozole has significant effects on breast cancer treatment and, therefore, it is currently used as first-line treatment in estrogen receptor (ER)-positive postmenopausal women, particularly to treat locally advanced or metastatic breast cancer. Furthermore, it is also indicated for early cancer treatment, tumor chemoprevention and postmenopausal women using tamoxifen, especially if the drug is used during a prolonged period of time and has been indicated in the disease’s recurrence, i.e., as another therapeutic endocrine option. Anastrozole is a nonsteroidal inhibitor of aromatase which effectively blocks estrogen synthesis in postmenopausal women and is used as therapy of estrogen receptor positive breast cancer. Anastrozole has been associated with a low rate of serum enzyme elevations during therapy and rare instances of clinically apparent liver injury.
• Therapeutic Function: Antitumor
• Clinical Use: Anastrozole is a potent and highly selective, nonsteroidal aromatase inhibitor utilized in the treatment of advanced breast cancer that is horm one-responsive. It is considered to be second-line therapy (after tamoxifen) in the treatment of postm enopaus al breast cancer.
• Drug interactions: Potentially hazardous interactions with other drugs Oestrogen-containing therapies: avoid concomitant administration as would negate pharmacological action. Tamoxifen: avoid concomitant administration.

Technology Process of Anastrozole

There total 26 articles about Anastrozole 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: 100.0%

1,2,4-Triazole (288-88-0) + 2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile (120511-84-4) → anastrozol (120511-73-1)

Guidance literature:

With potassium tert-butylate; In toluene; at 9 - 21 ℃; for 4.5h;

Reference yield: 90.0%

1,2,4-Triazole (288-88-0) + 3,5-bis(2-cyanopropan-2-yl)benzaldehyde (120511-89-9) → anastrozol (120511-73-1)

Guidance literature:

With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 45 - 55 ℃; for 7h; Reagent/catalyst; Solvent;

Reference yield: 82.0%

4-amino-1-[3,5-bis(1-cyano-1-methylethyl)benzyl]-4H-1,2,4-triazolium bromide → anastrozol (120511-73-1)

Guidance literature:

With sodium azide; sulfuric acid; copper(II) sulfate; In methanol; water; for 1h; Solvent; Reflux;

upstream raw materials:

α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile

anastrozole mesylate

2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile

sodium triazole

Downstream raw materials:

anastrozole mesylate

3,5-bis(2-cyanoprop-2-yl)toluene

Refernces

• 1、 -. "A process for synthesizing preparing anastrozole". Paragraph 0014; 0017-0018. . Retrieved 2017/01/23.
• 2、 -. "A method of synthesis of aromatase inhibitors". Paragraph 0036-0038. . Retrieved 2017/02/24.