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A2736

Sigma-Aldrich

Anastrozole

≥98% (HPLC)

Synonym(s):

2;2"-[5-(1H-1;2;4-Triazol-1-ylmethyl)-1, 3-Phenylene]bis(2-methyl-propiononitrile, Arimidex, ICI-D1033, ZD1033, a,a,a′,a′-Tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-benzenediacetonitrile

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About This Item

Empirical Formula (Hill Notation):
C17H19N5
CAS Number:
120511-73-1
Molecular Weight:
293.37
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

solubility

DMSO: 40 mg/mL

originator

AstraZeneca

storage temp.

room temp

InChI

1S/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

InChI key

YBBLVLTVTVSKRW-UHFFFAOYSA-N

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Application

Anastrozole (aromatase inhibitor) has been used:
  • as a positive control in DNA fragmentation (ladder) assay
  • to investigate its effects along with extra virgin olive oil and its major fatty acid component (omega-9 OA) in estrogen receptor positive mammary adenocarcinoma cells
  • to study its effects on viability, cell proliferation and apoptosis in Glioblastoma multiforme model in vivo

Biochem/physiol Actions

Anastrozole, which contains a triazole functional group, reversibly binds to the cytochrome P-450 component of aromatase. Binding interferes with the catalytic properties of aromatase, which results in inhibition of estrogen synthesis.
The aromatase enzyme converts adrenal androgens to estrogen; this enzymatic activity is the primary source of estrogen production in postmenopausal women. One treatment for estrogen receptor-positive breast cancer in postmenopausal women is through inhibition of aromatase. Anastrozole is a nonsteroidal, benzyl-triazole derivative that inhibits aromatase through competitive inhibition and is used to treat estrogen receptor-positive breast cancer. This compound is considered a third-generation, Type II aromatase inhibitor because it is more selective and less effective (if at all) on other steroidal hormones than first and second generation inhibitors.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H360FD

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Extra virgin olive oil potentiates the effects of aromatase inhibitors via glutathione depletion in estrogen receptor-positive human breast cancer (MCF-7) cells
Ismail AM, et al.
Food And Chemical Toxicology, 62(3), 817-824 (2013)
Dennis C Sgroi et al.
The Lancet. Oncology, 14(11), 1067-1076 (2013-09-17)
Biomarkers to improve the risk-benefit of extended adjuvant endocrine therapy for late recurrence in patients with oestrogen-receptor-positive breast cancer would be clinically valuable. We compared the prognostic ability of the breast-cancer index (BCI) assay, 21-gene recurrence score (Oncotype DX), and
Irene Guadalupe Aguilar-García et al.
Brain sciences, 13(3) (2023-03-30)
Glioblastoma Multiforme (GBM) is a tumor that infiltrates several brain structures. GBM is associated with abnormal motor activities resulting in impaired mobility, producing a loss of functional motor independence. We used a GBM xenograft implanted in the striatum to analyze
Anastrozole Reduce Cell Proliferation and Induce Apoptosis in Glioblastoma Multiforme Xenograft Mouse Model
Aguilar G, et al.
Journal of Cancer Science & Therapy, 9(3), 655-660 (2017)
Yanyan Hong et al.
Steroids, 76(8), 802-806 (2011-03-23)
Aromatase is the rate-limiting enzyme in estrogen biosynthesis. As a cytochrome P450, it utilizes electrons from NADPH-cytochrome P450 reductase (CPR) to produce estrogen from androgen. Estrogen is a key factor in the promotion of hormone-dependent breast cancer growth. Aromatase inhibitors
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