Anastrozole
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MedKoo CAT#: 100060

CAS#: 120511-73-1

Description: Anastrazole is a nonsteroidal inhibitor of estrogen synthesis that resembles paclitaxel in chemical structure. As a third-generation aromatase inhibitor, anastrozole selectively binds to and reversibly inhibits aromatase, a cytochrome P-450 enzyme complex found in many tissues including those of the premenopausal ovary, liver, and breast; aromatase catalyzes the aromatization of androstenedione and testosterone into estrone and estradiol, the final step in estrogen biosynthesis. In estrogen-dependent breast cancers, anastrozole may inhibit tumor growth. (


Chemical Structure

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Anastrozole
CAS# 120511-73-1

Theoretical Analysis

MedKoo Cat#: 100060
Name: Anastrozole
CAS#: 120511-73-1
Chemical Formula: C17H19N5
Exact Mass: 293.16405
Molecular Weight: 293.36626
Elemental Analysis: C, 69.60; H, 6.53; N, 23.87

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500.0mg USD 250.0 Same Day
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2.0g USD 650.0 Same Day
5.0g USD 950.0 Same Day
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20.0g USD 2450.0 Same Day
50.0g USD 3450.0 Same Day
500.0g USD 9850.0 2 Weeks
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Synonym: ZD-1033; ZD 1033; ZD1033; CCRIS 9352; HSDB 7462; ICI D1033; Anastrozole; Brand name: Arimidex. Abbreviation: ANAS.

IUPAC/Chemical Name: 2,2'-(5-((1H-1,2,4-triazol-1-yl)methyl)-1,3-phenylene)bis(2-methylpropanenitrile)

InChi Key: YBBLVLTVTVSKRW-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CC(C1=CC(CN2N=CN=C2)=CC(C(C)(C)C#N)=C1)(C)C#N

Appearance: white to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Anastrozole is an aromatase inhibitor, which inhibits human placental aromatase with an IC50 of 15 nM.
In vitro activity: Exposure to 100 nM MK-2206 induced a clear inhibition of the Akt pathway in both MCF-7aro and Res-Ana cell lines, as demonstrated by a significant decrease in the phosphorylation status of Akt, together with a significant decrease in the phosphorylation levels of GSK-3β and p70S6K (Fig. 3c). In accordance with their hyperactivated PI3K/Akt pathway, cytotoxicity assay revealed the Res-Ana cells to be significantly more sensitive to MK-2206 treatment alone than the MCF-7aro cells in both cell lines (Fig. 3d). Data illustrated in Figure 3d also showed in both MCF-7aro and Res-Ana cells that the combination of 100 nM MK-2206 with anastrozole (10−6 or 10−5 M) significantly increased the response when compared to anastrozole alone or to 100 nM MK-2206 alone. MK-2206 used at lower concentration (10 nM) gave similar results when combined with 10−5 M anastrozole (Fig. 3d). Finally, the cell viability observed in Res-Ana cells exposed to both MK-2206 (100 nM) and anastrozole was even lower than that observed in anastrozole-treated sensitive MCF-7aro cells (61.9 vs. 87% and 54.6 vs. 70.6%, p < 0.001). Reference: Int J Cancer. 2013 Oct 1;133(7):1589-602. https://onlinelibrary.wiley.com/doi/full/10.1002/ijc.28182
In vivo activity: This study’s observation that aromatase was among the genes which were upregulated by desflurane in the heart and it was abundantly expressed in endothelial and in smooth muscle cells in male mouse heart, let the study hypothesize that aromatase might also be involved in desflurane- induced cardioprotection in cardiac ischemia/reperfusion model. For this study, a highly selective fourth generation aromatase inhibitor anastrozole was utilized. This study demonstrated that aromatase inhibition by anastrozole at therapeutic concentrations (1 mg/kg BW) efficiently reduced local estrogen synthesis and thus blunted desflurane- induced cardioprotection in male mice without influencing cardiac function. Reference: PLoS One. 2012; 7(8): e42032. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3410886/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.59 177.45
DMF 14.0 47.72
Ethanol 36.11 123.09
Ethanol:PBS (pH 7.2) (1:9) 0.1 0.34

Preparing Stock Solutions

The following data is based on the product molecular weight 293.36626 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Topcul M, Cetin I, Ozlem Kolusayin Ozar M. The effects of anastrozole on the proliferation of FM3A cells. J BUON. 2013 Oct-Dec;18(4):874-8. PMID: 24344011. 2. Vilquin P, Villedieu M, Grisard E, Ben Larbi S, Ghayad SE, Heudel PE, Bachelot T, Corbo L, Treilleux I, Vendrell JA, Cohen PA. Molecular characterization of anastrozole resistance in breast cancer: pivotal role of the Akt/mTOR pathway in the emergence of de novo or acquired resistance and importance of combining the allosteric Akt inhibitor MK-2206 with an aromatase inhibitor. Int J Cancer. 2013 Oct 1;133(7):1589-602. doi: 10.1002/ijc.28182. Epub 2013 May 2. PMID: 23553037. 3. Chagas DC, Barros-Oliveira MDC, Lopes-Costa PV, Pereira RO, Melo MA, Costa-Silva DR, Borges CS, Viana JL, Santos ARD, Facina G, Silva BBD. Effects of anastrozole on Ki-67 antigen expression in the vaginal epithelium of female rats in persistent estrus. Clinics (Sao Paulo). 2020 Apr 3;75:e1643. doi: 10.6061/clinics/2020/e1643. PMID: 32267395; PMCID: PMC7098419. 4. Jazbutyte V, Stumpner J, Redel A, Lorenzen JM, Roewer N, Thum T, Kehl F. Aromatase inhibition attenuates desflurane-induced preconditioning against acute myocardial infarction in male mouse heart in vivo. PLoS One. 2012;7(8):e42032. doi: 10.1371/journal.pone.0042032. Epub 2012 Aug 2. PMID: 22876297; PMCID: PMC3410886.
In vitro protocol: 1. Topcul M, Cetin I, Ozlem Kolusayin Ozar M. The effects of anastrozole on the proliferation of FM3A cells. J BUON. 2013 Oct-Dec;18(4):874-8. PMID: 24344011. 2. Vilquin P, Villedieu M, Grisard E, Ben Larbi S, Ghayad SE, Heudel PE, Bachelot T, Corbo L, Treilleux I, Vendrell JA, Cohen PA. Molecular characterization of anastrozole resistance in breast cancer: pivotal role of the Akt/mTOR pathway in the emergence of de novo or acquired resistance and importance of combining the allosteric Akt inhibitor MK-2206 with an aromatase inhibitor. Int J Cancer. 2013 Oct 1;133(7):1589-602. doi: 10.1002/ijc.28182. Epub 2013 May 2. PMID: 23553037.
In vivo protocol: 1. Chagas DC, Barros-Oliveira MDC, Lopes-Costa PV, Pereira RO, Melo MA, Costa-Silva DR, Borges CS, Viana JL, Santos ARD, Facina G, Silva BBD. Effects of anastrozole on Ki-67 antigen expression in the vaginal epithelium of female rats in persistent estrus. Clinics (Sao Paulo). 2020 Apr 3;75:e1643. doi: 10.6061/clinics/2020/e1643. PMID: 32267395; PMCID: PMC7098419. 2. Jazbutyte V, Stumpner J, Redel A, Lorenzen JM, Roewer N, Thum T, Kehl F. Aromatase inhibition attenuates desflurane-induced preconditioning against acute myocardial infarction in male mouse heart in vivo. PLoS One. 2012;7(8):e42032. doi: 10.1371/journal.pone.0042032. Epub 2012 Aug 2. PMID: 22876297; PMCID: PMC3410886.

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1: Geisler J. Differences between the non-steroidal aromatase inhibitors anastrozole and letrozole--of clinical importance? Br J Cancer. 2011 Mar 29;104(7):1059-66. doi: 10.1038/bjc.2011.58. Epub 2011 Mar 1. Review. PubMed PMID: 21364577; PubMed Central PMCID: PMC3068499.

2: Kelly CM, Buzdar AU. Anastrozole. Expert Opin Drug Saf. 2010 Nov;9(6):995-1003. doi: 10.1517/14740338.2010.515977. Review. PubMed PMID: 20923259.

3: Nabholtz JM, Mouret-Reynier MA, Durando X, Van Praagh I, Al-Sukhun S, Ferriere JP, Chollet P. Comparative review of anastrozole, letrozole and exemestane in the management of early breast cancer. Expert Opin Pharmacother. 2009 Jun;10(9):1435-47. doi: 10.1517/14656560902953738. Review. PubMed PMID: 19445563.

4: Needleman SJ, Tobias JS. Review of the ATAC study: tamoxifen versus anastrozole in early-stage breast cancer. Expert Rev Anticancer Ther. 2008 Dec;8(12):1871-81. doi: 10.1586/14737140.8.12.1871. Review. PubMed PMID: 19046107.

5: Sanford M, Plosker GL. Anastrozole: a review of its use in postmenopausal women with early-stage breast cancer. Drugs. 2008;68(9):1319-40. Review. PubMed PMID: 18547136.

6: Graham PH. Anastrozole for malignant and benign conditions: present applications and future therapeutic integrations. Expert Opin Pharmacother. 2007 Oct;8(14):2347-57. Review. PubMed PMID: 17927488.

7: Bertoli LF, Barton JC. Remission of porphyria cutanea tarda after anastrozole treatment of breast cancer. Clin Breast Cancer. 2007 Aug;7(9):716-8. Review. PubMed PMID: 17919354.

8: van Nes JG, Seynaeve C, van de Velde CJ, Nortier JW. [Optimal adjuvant hormone therapy in postmenopausal women with hormone-sensitive mammary carcinoma: tamoxifen and the aromatase inhibitors anastrozole, exemestane and letrozole]. Ned Tijdschr Geneeskd. 2006 Dec 30;150(52):2863-9. Review. Dutch. PubMed PMID: 17319217.

9: Jakesz R. The adjuvant endocrine treatment revolution: focus on anastrozole. Expert Opin Drug Metab Toxicol. 2006 Apr;2(2):301-12. Review. PubMed PMID: 16866615.

10: Buzdar AU. Anastrozole for breast cancer: recent advances and ongoing challenges. Expert Rev Anticancer Ther. 2006 Jun;6(6):839-48. Review. PubMed PMID: 16761927. 



Additional Information

Anastrozole is an off-white powder with a molecular weight of 293.4. Anastrozole has moderate aqueous solubility (0.5 mg/mL at 25°C); solubility is independent of pH in the physiological range. Anastrozole is freely soluble in methanol, acetone, ethanol, and tetrahydrofuran, and very soluble in acetonitrile. Each tablet contains as inactive ingredients: lactose, magnesium stearate, hydroxypropylmethylcellulose, polyethylene glycol, povidone, sodium starch glycolate, and titanium dioxide.
 
The growth of many cancers of the breast is stimulated or maintained by estrogens. Treatment of breast cancer thought to be hormonally responsive (i.e., estrogen and/or progesterone receptor positive or receptor unknown) has included a variety of efforts to decrease estrogen levels (ovariectomy, adrenalectomy, hypophysectomy) or inhibit estrogen effects (antiestrogens and progestational agents). These interventions lead to decreased tumor mass or delayed progression of tumor growth in some women. In postmenopausal women, estrogens are mainly derived from the action of the aromatase enzyme, which converts adrenal androgens (primarily androstenedione and testosterone) to estrone and estradiol. The suppression of estrogen biosynthesis in peripheral tissues and in the cancer tissue itself can therefore be achieved by specifically inhibiting the aromatase enzyme. Anastrozole is a potent and selective non-steroidal aromatase inhibitor. It significantly lowers serum estradiol concentrations and has no detectable effect on formation of adrenal corticosteroids or aldosterone.
 
According to http://en.wikipedia.org/wiki/Anastrozole, Annual sales approx $2.2bn. Patent expires 2010 in the US[1]; however, the generic form is available in some other markets.