ANASTROZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H19N5
Molecular Weight	293.3669
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C#N)c1cc(cc(c1)C(C)(C)C#N)Cn2cncn2

InChI

InChIKey=YBBLVLTVTVSKRW-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H19N5
Molecular Weight	293.3669
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020541s029lbl.pdf

Anastrozole (marketed under the trade name Arimidex by AstraZeneca) is a drug indicated in the treatment of breast cancer in post-menopausal women. It is used both in adjuvant therapy (i.e. following surgery) and in metastatic breast cancer. It decreases the amount of estrogens that the body makes. Anastrozole belongs in the class of drugs known as aromatase inhibitors. It inhibits the enzyme aromatase, which is responsible for converting androgens (produced by women in the adrenal glands) to estrogens. The growth of many cancers of the breast is stimulated or maintained by estrogens. 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 selective non-steroidal aromatase inhibitor. It significantly lowers serum estradiol concentrations and has no detectable effect on formation of adrenal corticosteroids or aldosterone.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 19A1 35 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19794821	Inhibitor 7728

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 411 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020541s029lbl.pdf	Palliative		Approved 8043	ARIMIDEX Approved Use Anastrozole is an aromatase inhibitor indicated for: Adjuvant treatment of postmenopausal women with hormone receptor-positive early breast cancer ( 1.1) First-line treatment of postmenopausal women with hormone receptor-positive or hormone receptor unknown locally advanced or metastatic breast cancer ( 1.2) Treatment of advanced breast cancer in postmenopausal women with disease progression following tamoxifen therapy. Patients with ER-negative disease and patients who did not respond to previous tamoxifen therapy rarely responded to anastrozole ( 1.3) 1.1 Adjuvant Treatment Anastrozole tablets are indicated for adjuvant treatment of postmenopausal women with hormone receptor-positive early breast cancer. 1.2 First-Line Treatment Anastrozole tablets are indicated for the first-line treatment of postmenopausal women with hormone receptor-positive or hormone receptor unknown locally advanced or metastatic breast cancer. 1.3 Second-Line Treatment Anastrozole tablets are indicated for the treatment of advanced breast cancer in postmenopausal women with disease progression following tamoxifen therapy. Patients with ER-negative disease and patients who did not respond to previous tamoxifen therapy rarely responded to anastrozole tablets. Launch Date 8.2002241E11

C_max

Value	Dose	Co-administered	Analyte	Population
39.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19470631	1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		ANASTROZOLE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
648 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19470631	1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		ANASTROZOLE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1601	inhibitor 1604 substrate 936	inhibitor 1702 substrate 1118

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 627 CYP1A2 1383 CYP3A 191	CYP1A2 972 CYP2A6 485 CYP2B6 616 CYP2C8 634 CYP2C19 910 CYP2E1 606 CYP3A5 367 UGT1A1 393 UGT1A3 397 UGT1A4 330 UGT1A6 289 UGT1A7 221 UGT1A8 266 UGT1A9 357 UGT1A10 273 UGT2B4 233 UGT2B7 362 UGT2B15 191 UGT2B17 203 P-gp 1400 BCRP 515

Drug as perpetrator

Target	Modality	Activity
CYP2A6 659	inhibitor 3045 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	no
CYP2D6 1738	inhibitor 3045 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	no
CYP2C9 1648	inhibitor 3045 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	yes [Ki 10 uM]
CYP3A 271	inhibitor 3045 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	yes [Ki 10 uM]
CYP1A2 1532	inhibitor 3045 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	yes [Ki 8 uM]

Drug as victim

Target	Modality	Activity
CYP2B6 616	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	low
CYP2C8 634	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	low
CYP2D6 1118	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	low
CYP3A4 1601	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	major
UGT1A4 330	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	major
CYP3A5 367	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	minor
UGT1A3 397	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	minor
UGT2B7 362	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	minor
BCRP 515	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/23712697/	no
CYP1A2 972	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2A6 485	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2C19 910	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2C9 936	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2E1 606	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A1 393	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A10 273	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A6 289	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A7 221	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A8 266	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A9 357	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT2B15 191	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT2B17 203	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT2B4 233	substrate 3113 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
P-gp 1400	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/23712697/; https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5306492/#bcp13130-bib-0009	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2704	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2704
ChemicalBook	CB3121715	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3121715
Selleck Chemicals	Anastrozole	http://www.selleckchem.com/products/Anastrozole.html
ZINC	ZINC000000000941	http://zinc15.docking.org/substances/ZINC000000000941
eMolecules	27516220	https://www.emolecules.com/cgi-bin/more?vid=27516220
eMolecules	901391	https://www.emolecules.com/cgi-bin/more?vid=901391

PubMed

Title	Date	PubMed
Pure antiestrogens and breast cancer.	2001	11922402
Aromatase and aromatase inhibitors.	2001	11791126
Third-generation aromatase inhibitors in the treatment of advanced breast cancer.	2001	11791122
Anastrozole: pharmacological and clinical profile in postmenopausal women with breast cancer.	2001 Aug	12113022
Promising results for Arimidex and Femara.	2001 Dec	12113080
Future use of selective estrogen receptor modulators and aromatase inhibitors.	2001 Dec	11916232
Preliminary data from ongoing adjuvant aromatase inhibitor trials.	2001 Dec	11916231
Where do selective estrogen receptor modulators (SERMs) and aromatase inhibitors (AIs) now fit into breast cancer treatment algorithms?	2001 Dec	11850229
Faslodex (ICI 182, 780), a novel estrogen receptor downregulator--future possibilities in breast cancer.	2001 Dec	11850227
Adjuvant trials of aromatase inhibitors: determining the future landscape of adjuvant endocrine therapy.	2001 Dec	11850217
Comparative clinical pharmacology and pharmacokinetic interactions of aromatase inhibitors.	2001 Dec	11850211
High dehydroepiandrosterone-sulfate predicts breast cancer progression during new aromatase inhibitor therapy and stimulates breast cancer cell growth in tissue culture: a renewed role for adrenalectomy.	2001 Dec	11742322
HER-2 amplification impedes the antiproliferative effects of hormone therapy in estrogen receptor-positive primary breast cancer.	2001 Dec 1	11731427
Pharmacokinetics of anastrozole in Chinese male volunteers.	2001 Jun	11747767
Anastrozole (Arimidex)--an aromatase inhibitor for the adjuvant setting?	2001 Nov	11900212
A vision for the future?	2001 Nov	11900211
ICI 182,780 (Fulvestrant)--the first oestrogen receptor down-regulator--current clinical data.	2001 Nov	11900210
Formestane, a steroidal aromatase inhibitor after failure of non-steroidal aromatase inhibitors (anastrozole and letrozole): is a clinical benefit still achievable?	2001 Nov	11822752
Anastrozole is superior to tamoxifen as first-line therapy in hormone receptor positive advanced breast carcinoma.	2001 Nov 1	11745278
Tamoxifen vs the aromatase inhibitors: news from San Antonio, 2001.	2001 Nov-Dec	11807416
Finding the needle in the haystack: why high-throughput screening is good for your health.	2002	12100740
Estrogen as therapy for breast cancer.	2002	12100736
Recent advances in breast cancer (the Twenty-fourth San Antonio Breast Cancer Symposium, December, 2001).	2002	11999142
Tamoxifen resistant and refractory breast cancer: the value of aromatase inhibitors.	2002	11929341
Aromatase inhibitors continue their ATAC on tamoxifen.	2002	11927281
Estrogen receptor downregulators: new antihormonal therapy for advanced breast cancer.	2002	11911506
Existing and emerging endocrine therapies for breast cancer.	2002 Apr	12080538
The oncology nurse's role in educating patients on endocrine therapy for metastatic breast cancer--focus on fulvestrant.	2002 Apr	12080536
[The role of aromatase inhibitors in the treatment of breast neoplasms. An evaluation of clinical efficacy and the tolerability profile].	2002 Apr	12032450
Antiaromatase agents: evolving role in adjuvant therapy.	2002 Apr	12020394
Short-term effects of anastrozole treatment on insulin-like growth factor system in postmenopausal advanced breast cancer patients.	2002 Apr	11983488
New breast cancer drugs expand treatment options.	2002 Apr	11959538
Effects of aromatase inhibition on in vitro follicle and oocyte development analyzed by early preantral mouse follicle culture.	2002 Apr	11891927
Aromatase inhibitors for male infertility.	2002 Feb	11792932
Influence of letrozole and anastrozole on total body aromatization and plasma estrogen levels in postmenopausal breast cancer patients evaluated in a randomized, cross-over study.	2002 Feb 1	11821457
Hormones 'R' us.	2002 Jan	11899355
[Aromatase inhibitors of the 3rd generation. What can the "pill against breast cancer" really do?].	2002 Jan 31	11883037
Endocrine effects of nonsteroidal aromatase inhibitors and their clinical impact.	2002 Jul 1	12089238
Letrozole for the management of breast cancer.	2002 Jun	12113048
[Antiestrogen therapy in the treatment of breast neoplasms].	2002 Jun	12063440
Efficacy of anastrozole in male breast cancer.	2002 Jun	12040279
Aromatase inhibition for ovarian stimulation: future avenues for infertility management.	2002 Jun	12032380
Anastrozole alone or in combination with tamoxifen versus tamoxifen alone for adjuvant treatment of postmenopausal women with early breast cancer: first results of the ATAC randomised trial.	2002 Jun 22	12090977
Experience of hormonal therapy with anastrozole for previously treated metastatic breast cancer.	2002 Mar	11908256
Aromatase inhibitors in breast cancer.	2002 Mar	11854020
Detection of aromatase inhibitors in vitro using rat ovary microsomes.	2002 Mar 24	11879982
Endocrine and clinical endpoints of exemestane as neoadjuvant therapy.	2002 Mar-Apr	11965226
Anti-aromatase agents in the treatment and prevention of breast cancer.	2002 Mar-Apr	11965225
Factors affecting progression-free survival in hormone-dependent metastatic breast cancer patients receiving high-dose chemotherapy and hematopoietic progenitor cell transplantation: role of maintenance endocrine therapy.	2002 May	12058236
A better medication for treating breast cancer?	2002 May	12004835

Patents

Sample Use Guides

In Vivo Use Guide

One 1 mg tablet taken once daily

Route of Administration: Oral

In Vitro Use Guide

Anastrozole, aromatase inhibitor was added at a concentration of 200 and 300 μg/mL to the endometrioma cells. The use of anastrozole significantly inhibited the growth of endometrioma cells, and estradiol secretion.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:04:22 UTC 2021` Edited by `admin` on `Fri Jun 25 21:04:22 UTC 2021`
Record UNII	2Z07MYW1AZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANASTROZOLE

Official Name

English

ANASTROZOLE [HSDB]

Common Name

English

ANASTROZOLE [ORANGE BOOK]

Common Name

English

ANASTROZOLE [MART.]

Common Name

English

ZD1033

Code

English

ANASTROZOLE [USP]

Common Name

English

ANASTROZOLE [USP-RS]

Common Name

English

ZD-1033

Code

English

ICI-D1033

Code

English

ANASTROZOLE [WHO-DD]

Common Name

English

ANASTROZOLE [JAN]

Common Name

English

NSC-759855

Code

English

ANASTROZOLE [EP MONOGRAPH]

Common Name

English

ANASTROZOLE [MI]

Common Name

English

NSC-719344

Code

English

ANASTROZOLE [INN]

Common Name

English

1,3-BENZENEDIACETONITRILE,.ALPHA.,.ALPHA.,.ALPHA.',.ALPHA.'-TETRAMETHYL-5-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-

Common Name

English

ICI D1033

Code

English

ARIMIDEX

Brand Name

English

ANASTROZOLE [USP MONOGRAPH]

Common Name

English

RVG-106400

Common Name

English

ANASTROZOLE [USAN]

Common Name

English

.ALPHA.,.ALPHA.,.ALPHA.',.ALPHA.'-TETRAMETHYL-5-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-M-BENZENEDIACETONITRILE

Systematic Name

English

Classification Tree Code System Code

NDF-RT

N0000175563