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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19794821 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | ARIMIDEX Approved UseAnastrozole 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 Date8.2002241E11 |
Cmax
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 |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
yes [Ki 10 uM] | ||||
yes [Ki 10 uM] | ||||
yes [Ki 8 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25839436
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
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Wed Jul 05 23:22:18 UTC 2023
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2Z07MYW1AZ
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Validated (UNII)
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NDF-RT |
N0000175563
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WHO-VATC |
QL02BG03
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WHO-ATC |
L02BG03
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NCI_THESAURUS |
C2018
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NDF-RT |
N0000175080
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LIVERTOX |
NBK548189
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DB01217
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2Z07MYW1AZ
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5137
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HH-1
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120511-73-1
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759855
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2Z07MYW1AZ
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CHEMBL1399
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7274
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84857
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M1889
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100000092332
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719344
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ANASTROZOLE
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1034807
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2704
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C1607
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C090450
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
lacks pharmacologic activity
MAJOR
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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