ANASTROZOLE

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 Search

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

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 38 Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19794821	Inhibitor 8228

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 431 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020541s029lbl.pdf	Palliative		Approved 8360	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 1709	inhibitor 1752 substrate 1010	inhibitor 1837 substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 704 CYP1A2 1509 CYP3A 211	CYP1A2 1032 CYP2A6 523 CYP2B6 660 CYP2C8 688 CYP2C19 985 CYP2E1 648 CYP3A5 391 UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 290 UGT2B4 249 UGT2B7 389 UGT2B15 203 UGT2B17 213 P-gp 1527 BCRP 555

Drug as perpetrator

Target	Modality	Activity
CYP2A6 736	inhibitor 3240 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	no
CYP2D6 1875	inhibitor 3240 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	no
CYP2C9 1803	inhibitor 3240 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	yes [Ki 10 uM]
CYP3A 295	inhibitor 3240 Sources: https://dmd.aspetjournals.org/content/25/5/598?ijkey=f5f4a077bb1bf0fceb9b8a924da966fe45108323&keytype2=tf_ipsecsha	yes [Ki 10 uM]
CYP1A2 1673	inhibitor 3240 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 660	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	low
CYP2C8 688	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	low
CYP2D6 1193	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	low
CYP3A4 1709	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	major
UGT1A4 347	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	major
CYP3A5 391	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	minor
UGT1A3 422	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	minor
UGT2B7 389	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	minor
BCRP 555	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/23712697/	no
CYP1A2 1032	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2A6 523	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2C19 985	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2C9 1010	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
CYP2E1 648	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A1 418	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A10 290	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A6 307	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A7 236	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A8 283	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT1A9 380	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT2B15 203	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT2B17 213	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
UGT2B4 249	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3014069/	no
P-gp 1527	substrate 3326 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
Aromatase inhibitors.	2001	11900315
Aromatase and aromatase inhibitors.	2001	11791126
Fulvestrant.	2001	11398912
Breast cancer chemoprevention: beyond tamoxifen.	2001	11250754
Nonsteroidal and steroidal aromatase inhibitors in breast cancer.	2001 Aug	11548977
Future use of selective estrogen receptor modulators and aromatase inhibitors.	2001 Dec	11916232
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
Intracellular aromatase and its relevance to the pharmacological efficacy of aromatase inhibitors.	2001 Jan-Mar	11384878
Pharmacokinetics of anastrozole in Chinese male volunteers.	2001 Jun	11747767
Endocrine therapy in the treatment of metastatic breast cancer.	2001 Jun	11402439
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	11397860
The effect of anastrozole on the single-dose pharmacokinetics and anticoagulant activity of warfarin in healthy volunteers.	2001 May	11422000
Is anastrozole superior to tamoxifen as first-line therapy for advanced breast cancer?	2001 May 1	11331344
Advances in aromatase inhibition: clinical efficacy and tolerability in the treatment of breast cancer.	2001 Sep	11555572
Aromatase inhibitors continue their ATAC on tamoxifen.	2002	11927281
Existing and emerging endocrine therapies for breast cancer.	2002 Apr	12080538
[The role of aromatase inhibitors in the treatment of breast neoplasms. An evaluation of clinical efficacy and the tolerability profile].	2002 Apr	12032450
Short-term effects of anastrozole treatment on insulin-like growth factor system in postmenopausal advanced breast cancer patients.	2002 Apr	11983488
Hormones 'R' us.	2002 Jan	11899355
Efficacy of anastrozole in male breast cancer.	2002 Jun	12040279

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 `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

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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

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