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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

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

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
Pure antiestrogens and breast cancer.
2001
Aromatase and aromatase inhibitors.
2001
Third-generation aromatase inhibitors in the treatment of advanced breast cancer.
2001
Anastrozole: pharmacological and clinical profile in postmenopausal women with breast cancer.
2001 Aug
Promising results for Arimidex and Femara.
2001 Dec
Future use of selective estrogen receptor modulators and aromatase inhibitors.
2001 Dec
Preliminary data from ongoing adjuvant aromatase inhibitor trials.
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
Adjuvant trials of aromatase inhibitors: determining the future landscape of adjuvant endocrine therapy.
2001 Dec
Comparative clinical pharmacology and pharmacokinetic interactions of aromatase inhibitors.
2001 Dec
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
HER-2 amplification impedes the antiproliferative effects of hormone therapy in estrogen receptor-positive primary breast cancer.
2001 Dec 1
Pharmacokinetics of anastrozole in Chinese male volunteers.
2001 Jun
Anastrozole (Arimidex)--an aromatase inhibitor for the adjuvant setting?
2001 Nov
A vision for the future?
2001 Nov
ICI 182,780 (Fulvestrant)--the first oestrogen receptor down-regulator--current clinical data.
2001 Nov
Formestane, a steroidal aromatase inhibitor after failure of non-steroidal aromatase inhibitors (anastrozole and letrozole): is a clinical benefit still achievable?
2001 Nov
Anastrozole is superior to tamoxifen as first-line therapy in hormone receptor positive advanced breast carcinoma.
2001 Nov 1
Tamoxifen vs the aromatase inhibitors: news from San Antonio, 2001.
2001 Nov-Dec
Finding the needle in the haystack: why high-throughput screening is good for your health.
2002
Estrogen as therapy for breast cancer.
2002
Recent advances in breast cancer (the Twenty-fourth San Antonio Breast Cancer Symposium, December, 2001).
2002
Tamoxifen resistant and refractory breast cancer: the value of aromatase inhibitors.
2002
Aromatase inhibitors continue their ATAC on tamoxifen.
2002
Estrogen receptor downregulators: new antihormonal therapy for advanced breast cancer.
2002
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
[The role of aromatase inhibitors in the treatment of breast neoplasms. An evaluation of clinical efficacy and the tolerability profile].
2002 Apr
Antiaromatase agents: evolving role in adjuvant therapy.
2002 Apr
Short-term effects of anastrozole treatment on insulin-like growth factor system in postmenopausal advanced breast cancer patients.
2002 Apr
New breast cancer drugs expand treatment options.
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
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
Hormones 'R' us.
2002 Jan
[Aromatase inhibitors of the 3rd generation. What can the "pill against breast cancer" really do?].
2002 Jan 31
Endocrine effects of nonsteroidal aromatase inhibitors and their clinical impact.
2002 Jul 1
Letrozole for the management of breast cancer.
2002 Jun
[Antiestrogen therapy in the treatment of breast neoplasms].
2002 Jun
Efficacy of anastrozole in male breast cancer.
2002 Jun
Aromatase inhibition for ovarian stimulation: future avenues for infertility management.
2002 Jun
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
Experience of hormonal therapy with anastrozole for previously treated metastatic breast cancer.
2002 Mar
Aromatase inhibitors in breast cancer.
2002 Mar
Detection of aromatase inhibitors in vitro using rat ovary microsomes.
2002 Mar 24
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
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
A better medication for treating breast cancer?
2002 May
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.
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
  • Download
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
Related Record Type Details
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
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METABOLITE -> PARENT
lacks pharmacologic activity
MAJOR
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC