U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H19N5
Molecular Weight 293.3663
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANASTROZOLE

SMILES

CC(C)(C#N)C1=CC(=CC(CN2C=NC=N2)=C1)C(C)(C)C#N

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 293.3663
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
Aromatase inhibitors.
2001
Aromatase and aromatase inhibitors.
2001
Fulvestrant.
2001
Breast cancer chemoprevention: beyond tamoxifen.
2001
Nonsteroidal and steroidal aromatase inhibitors in breast cancer.
2001 Aug
Future use of selective estrogen receptor modulators and aromatase inhibitors.
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
Intracellular aromatase and its relevance to the pharmacological efficacy of aromatase inhibitors.
2001 Jan-Mar
Pharmacokinetics of anastrozole in Chinese male volunteers.
2001 Jun
Endocrine therapy in the treatment of metastatic breast cancer.
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
The effect of anastrozole on the single-dose pharmacokinetics and anticoagulant activity of warfarin in healthy volunteers.
2001 May
Is anastrozole superior to tamoxifen as first-line therapy for advanced breast cancer?
2001 May 1
Advances in aromatase inhibition: clinical efficacy and tolerability in the treatment of breast cancer.
2001 Sep
Aromatase inhibitors continue their ATAC on tamoxifen.
2002
Existing and emerging endocrine therapies for breast cancer.
2002 Apr
[The role of aromatase inhibitors in the treatment of breast neoplasms. An evaluation of clinical efficacy and the tolerability profile].
2002 Apr
Short-term effects of anastrozole treatment on insulin-like growth factor system in postmenopausal advanced breast cancer patients.
2002 Apr
Hormones 'R' us.
2002 Jan
Efficacy of anastrozole in male breast cancer.
2002 Jun
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 Wed Jul 05 23:22:18 UTC 2023
Edited
by admin
on Wed Jul 05 23:22:18 UTC 2023
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
Anastrozole [WHO-DD]
Common Name English
ZD1033
Code English
ANASTROZOLE [USP IMPURITY]
Common Name English
ANASTROZOLE [USP-RS]
Common Name English
ZD-1033
Code English
ICI-D1033
Code 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 Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
WHO-VATC QL02BG03
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
WHO-ATC L02BG03
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
NCI_THESAURUS C2018
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
NDF-RT N0000175080
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
LIVERTOX NBK548189
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID9022607
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
DRUG BANK
DB01217
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
HSDB
7462
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
DAILYMED
2Z07MYW1AZ
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
IUPHAR
5137
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
USAN
HH-1
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
PUBCHEM
2187
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
DRUG CENTRAL
210
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
EVMPD
SUB05502MIG
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
CAS
120511-73-1
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
NSC
759855
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
FDA UNII
2Z07MYW1AZ
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL1399
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
INN
7274
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
RXCUI
84857
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M1889
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY Merck Index
SMS_ID
100000092332
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
NSC
719344
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
WIKIPEDIA
ANASTROZOLE
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
RS_ITEM_NUM
1034807
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
CHEBI
2704
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
NCI_THESAURUS
C1607
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
MESH
C090450
Created by admin on Wed Jul 05 23:22:18 UTC 2023 , Edited by admin on Wed Jul 05 23:22:18 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE -> PARENT
lacks pharmacologic activity
MAJOR
Related Record Type Details
IMPURITY -> PARENT
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)
USP
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