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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 of ANASTROZOLE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
39.3 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
648 ng × h/mL
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
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
low
low
low
major
major
minor
minor
minor
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
PubMed

PubMed

TitleDatePubMed
Aromatase and aromatase inhibitors.
2001
Third-generation aromatase inhibitors in the treatment of advanced breast cancer.
2001
New combinations with Herceptin in metastatic breast cancer.
2001
[Modern approaches to hormone therapy of breast cancer as a reflection of pathogenesis of the disease].
2001
Update on endocrine aspects of breast cancer: report from the 23rd San Antonio Breast Cancer Symposium, San Antonio, Texas, USA, 6-9 December 2000.
2001
[Development of a novel aromatase inhibitor, anastrozole (Arimidex)--its basic and clinical studies].
2001 Apr
Anastrozole: pharmacological and clinical profile in postmenopausal women with breast cancer.
2001 Aug
Exemestane: new preparation. No tangible advance in metastatic breast cancer after tamoxifen failure.
2001 Aug
Pharmacokinetics of anastrozole and tamoxifen alone, and in combination, during adjuvant endocrine therapy for early breast cancer in postmenopausal women: a sub-protocol of the 'Arimidex and tamoxifen alone or in combination' (ATAC) trial.
2001 Aug 3
Promising results for Arimidex and Femara.
2001 Dec
Future use of selective estrogen receptor modulators and aromatase inhibitors.
2001 Dec
The role of tamoxifen and aromatase inhibitors/inactivators in postmenopausal patients.
2001 Dec
Where do selective estrogen receptor modulators (SERMs) and aromatase inhibitors (AIs) now fit into breast cancer treatment algorithms?
2001 Dec
Faslodex (ICI 182, 780), a novel estrogen receptor downregulator--future possibilities in breast cancer.
2001 Dec
Biological and clinical effects of aromatase inhibitors in neoadjuvant therapy.
2001 Dec
HER-2 amplification impedes the antiproliferative effects of hormone therapy in estrogen receptor-positive primary breast cancer.
2001 Dec 1
Intracellular aromatase and its relevance to the pharmacological efficacy of aromatase inhibitors.
2001 Jan-Mar
Anastrozole: licence extension. No advantage over tamoxifen in advanced-stage breast cancer.
2001 Jun
Endocrine therapy in the treatment of metastatic breast cancer.
2001 Jun
The effect of aromatase inhibition on sex steroids, gonadotropins, and markers of bone turnover in older men.
2001 Jun
Aromatization mediates testosterone's short-term feedback restraint of 24-hour endogenously driven and acute exogenous gonadotropin-releasing hormone-stimulated luteinizing hormone and follicle-stimulating hormone secretion in young men.
2001 Jun
[Aromatase inhibitors: anastrozole versus tamoxifen as first-ine therapy for advanced postmenopausal breast cancer].
2001 May
Aromatase inhibition and antiestrogen therapy in early breast cancer treatment and chemoprevention.
2001 May
[Evolvement of hormone therapy for breast cancer. Florence, March 14, 2001].
2001 May-Jun
Anastrozole is superior to tamoxifen as first-line therapy in hormone receptor positive advanced breast carcinoma.
2001 Nov 1
Role of anti-aromatase agents in postmenopausal advanced breast cancer.
2001 Oct
Use of the aromatase inhibitor anastrozole in the treatment of patients with advanced prostate carcinoma.
2001 Oct 15
Aromatase inhibitors and inactivators in breast cancer.
2001 Oct 20
Advances in aromatase inhibition: clinical efficacy and tolerability in the treatment of breast cancer.
2001 Sep
Aromatase, aromatase inhibitors, and breast cancer.
2001 Sep-Oct
Estrogen as therapy for breast cancer.
2002
Estrogen receptor downregulators: new antihormonal therapy for advanced breast cancer.
2002
Gateways to Clinical Trials.
2002 Apr
Existing and emerging endocrine therapies for breast cancer.
2002 Apr
The oncology nurse's role in educating patients on endocrine therapy for metastatic breast cancer--focus on fulvestrant.
2002 Apr
Antiaromatase agents: evolving role in adjuvant therapy.
2002 Apr
Effects of aromatase inhibition on in vitro follicle and oocyte development analyzed by early preantral mouse follicle culture.
2002 Apr
Aromatase inhibitors for male infertility.
2002 Feb
Hormones 'R' us.
2002 Jan
Endocrine effects of nonsteroidal aromatase inhibitors and their clinical impact.
2002 Jul 1
Letrozole for the management of breast cancer.
2002 Jun
Aromatase inhibitors for the endocrine adjuvant treatment of breast cancer.
2002 Jun 22
Experience of hormonal therapy with anastrozole for previously treated metastatic breast cancer.
2002 Mar
Aromatase inhibitors in breast cancer.
2002 Mar
Endocrine and clinical endpoints of exemestane as neoadjuvant therapy.
2002 Mar-Apr
Anti-aromatase agents in the treatment and prevention of breast cancer.
2002 Mar-Apr
Patents

Sample Use Guides

One 1 mg tablet taken once daily
Route of Administration: Oral
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.
Name Type Language
ANASTROZOLE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
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
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
WHO-VATC QL02BG03
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
WHO-ATC L02BG03
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
NCI_THESAURUS C2018
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
NDF-RT N0000175080
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
LIVERTOX 56
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
Code System Code Type Description
EPA CompTox
120511-73-1
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
DRUG BANK
DB01217
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
HSDB
7462
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
IUPHAR
5137
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
PUBCHEM
2187
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
DRUG CENTRAL
210
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
EVMPD
SUB05502MIG
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
CAS
120511-73-1
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
FDA UNII
2Z07MYW1AZ
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL1399
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
USP_CATALOG
1034807
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY USP-RS
INN
7274
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
RXCUI
84857
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M1889
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
ANASTROZOLE
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
NCI_THESAURUS
C1607
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY
MESH
C090450
Created by admin on Fri Jun 25 21:04:23 UTC 2021 , Edited by admin on Fri Jun 25 21:04:23 UTC 2021
PRIMARY