Identification
NameAnastrozole
Accession NumberDB01217  (APRD00016)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Anastrozole 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.

Structure
Thumb
Synonyms
alpha,alpha,Alpha',alpha'-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-m-benzenediacetonitrile
Anastrozol
External IDs ICI D1033 / ICI-D1033 / ZD-1033 / ZD1033
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-anastrozole TabletsTablet1 mgOralAccel Pharma IncNot applicableNot applicableCanada
Ach-anastrozoleTablet1 mgOralAccord Healthcare Limited2012-10-25Not applicableCanada
Act AnastrozoleTablet1 mgOralActavis Pharma Company2012-10-25Not applicableCanada
AnastrozoleTablet1 mgOralPro Doc Limitee2012-11-22Not applicableCanada
AnastrozoleTablet1 mgOralCellchem Pharmaceuticals Inc.Not applicableNot applicableCanada
AnastrozoleTablet1 mgOralSanis Health Inc2015-07-22Not applicableCanada
ArimidexTablet1 mg/1OralPhysicians Total Care, Inc.2004-02-19Not applicableUs
ArimidexTablet1 mg/1OralAstra Zeneca Lp1996-01-16Not applicableUs
Arimidex Tab 1mgTablet1 mgOralAstra Zeneca1996-08-30Not applicableCanada
Auro-anastrozoleTablet1 mgOralAuro Pharma Inc2013-06-12Not applicableCanada
Bio-anastrozoleTablet1 mgOralBiomed Pharma2013-01-15Not applicableCanada
Dom-anastrozoleTablet1 mgOralDominion PharmacalNot applicableNot applicableCanada
Ipg-anastrozoleTablet1 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-anastrozoleTablet1 mgOralJamp Pharma Corporation2012-10-25Not applicableCanada
Mar-anastrozoleTablet1 mgOralMarcan Pharmaceuticals Inc2012-10-25Not applicableCanada
Med-anastrozoleTablet1 mgOralGeneric Medical Partners Inc2012-10-25Not applicableCanada
Mint-anastrozoleTablet1 mgOralMint Pharmaceuticals Inc2012-10-25Not applicableCanada
Mylan-anastrozoleTablet1 mgOralMylan Pharmaceuticals2012-10-252017-01-09Canada
Nat-anastrozoleTablet1 mgOralNatco Pharma Limited2015-02-03Not applicableCanada
PMS-anastrozoleTablet1 mgOralPharmascience Inc2012-10-25Not applicableCanada
Ran-anastrozoleTablet1 mgOralRanbaxy Inc.2012-10-25Not applicableCanada
Riva-anastrozoleTablet1 mgOralLaboratoire Riva Inc2012-10-26Not applicableCanada
Sandoz AnastrozoleTablet1 mgOralSandoz Canada Incorporated2012-07-26Not applicableCanada
Taro-anastrozoleTablet1 mgOralTaro Pharmaceuticals, Inc.2012-10-25Not applicableCanada
Teva-anastrozoleTablet1 mgOralTeva2012-10-25Not applicableCanada
Van-anastrozoleTablet1 mgOralVanc Pharmaceuticals Inc2015-06-08Not applicableCanada
Zinda-anastrozoleTablet1 mgOralStason Pharmaceuticals, Inc.2013-06-18Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AnastrozoleTablet1 mg/1OralRebel Distributors2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralAscend Laboratories, LLC2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralA S Medication Solutions2010-06-282017-06-20Us
AnastrozoleTablet1 mg/1OralBreckenridge Pharmaceutical, Inc.2010-06-28Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralTeva2010-06-28Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralGolden State Medical Supply2011-08-22Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralSynthon Pharmaceuticals, Inc.2010-06-28Not applicableUs
AnastrozoleTablet, coated1 mg/1OralAmerincan Health Packaging2015-11-01Not applicableUs
AnastrozoleTablet1 mg/1OralMajor2010-06-15Not applicableUs
AnastrozoleTablet1 mg/1OralA S Medication Solutions2010-06-012017-06-20Us
AnastrozoleTablet, film coated1 mg/1OralKadmon Pharmaceuticals2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralNorthwind Pharmaceuticals2014-11-07Not applicableUs
AnastrozoleTablet, coated1 mg/1OralZydus Pharmaceuticals Usa, Inc.2010-06-27Not applicableUs
AnastrozoleTablet1 mg/1OralA S Medication Solutions2010-06-282017-06-20Us
AnastrozoleTablet1 mg/1OralStason Pharmaceuticals, Inc.2010-06-282017-04-25Us
AnastrozoleTablet1 mg/1OralStason Pharmaceuticals, Inc.2017-04-10Not applicableUs
AnastrozoleTablet1 mg/1OralProficient Rx LP2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralAccord Healthcare Limited2010-06-22Not applicableUs
AnastrozoleTablet, coated1 mg/1OralCadila Pharnmaceuticals2010-06-27Not applicableUs
AnastrozoleTablet1 mg/1OralPd Rx Pharmaceuticals, Inc.2010-06-28Not applicableUs
AnastrozoleTablet, coated1 mg/1OralBlue Point Laboratories2014-01-01Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralA S Medication Solutions2010-07-162017-06-20Us
AnastrozoleTablet1 mg/1OralPhysicians Total Care, Inc.2010-07-01Not applicableUs
AnastrozoleTablet1 mg/1OralKaiser Foundations Hospitals2010-07-13Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralApotex Corporation2012-05-31Not applicableUs
AnastrozoleTablet1 mg/1OralAvera Mc Kennan Hospital2015-03-01Not applicableUs
AnastrozoleTablet1 mg/1OralPreferreed Pharmaceuticals Inc.2016-10-24Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralKremers Urban2011-01-05Not applicableUs
AnastrozoleTablet1 mg/1OralMajor2010-12-26Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralMylan Pharmaceuticals2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralWest Ward Pharmaceutical2010-06-282018-03-08Us
AnastrozoleTablet1 mg/1OralAPP Pharmaceuticals, Inc.2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralRebel Distributors2010-07-01Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralSandoz2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1Oralbryant ranch prepack2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralDispensing Solutions, Inc.2010-06-28Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralUDL Laboratories, Inc.2010-07-232016-11-11Us
AnastrozoleTablet, coated1 mg/1OralAmerincan Health Packaging2010-06-272017-01-31Us
AnastrozoleTablet, film coated1 mg/1OralA S Medication Solutions2012-05-312017-06-20Us
AnastrozoleTablet, film coated1 mg/1OralDr Reddy's Laboratories2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralA S Medication Solutions2010-06-222017-06-20Us
AnastrozoleTablet, film coated1 mg/1OralSun Pharmaceutical Industries Limited2010-07-162017-02-11Us
AnastrozoleTablet1 mg/1OralRising Pharmaceuticals2010-06-01Not applicableUs
Apo-anastrozoleTablet1 mgOralApotex Corporation2012-10-25Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AnastroleNot Available
Brand mixturesNot Available
Categories
UNII2Z07MYW1AZ
CAS number120511-73-1
WeightAverage: 293.3663
Monoisotopic: 293.164045633
Chemical FormulaC17H19N5
InChI KeyYBBLVLTVTVSKRW-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-[3-(1-cyano-1-methylethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
SMILES
CC(C)(C#N)C1=CC(=CC(CN2C=NC=N2)=C1)C(C)(C)C#N
Pharmacology
Indication

For adjuvant treatment of hormone receptor positive breast cancer , as well as hormonal treatment of advanced breast cancer in post-menopausal women. Has also been used to treat pubertal gynecomastia and McCune-Albright syndrome; however, manufacturer states that efficacy for these indications have not been established.

Structured Indications
Pharmacodynamics

Anastrozole is a potent and selective non-steroidal aromatase inhibitor indicated for the treatment of advanced breast cancer in post-menopausal women with disease progression following tamoxifen therapy. Many breast cancers have estrogen receptors and growth of these tumors can be stimulated by estrogens. In post-menopausal women, the principal source of circulating estrogen (primarily estradiol) is conversion of adrenally-generated androstenedione to estrone by aromatase in peripheral tissues, such as adipose tissue, with further conversion of estrone to estradiol. Many breast cancers also contain aromatase; the importance of tumor-generated estrogens is uncertain. Treatment of breast cancer has included efforts to decrease estrogen levels by ovariectomy premenopausally and by use of anti-estrogens and progestational agents both pre- and post-menopausally, and these interventions lead to decreased tumor mass or delayed progression of tumor growth in some women. Anastrozole is a potent and selective non-steroidal aromatase inhibitor. It significantly lowers serum estradiol concentrations and has no detectable effect on formation of adrenal corticosteroids or aldosterone.

Mechanism of action

Anastrozole selectively inhibits aromatase. The principal source of circulating estrogen (primarily estradiol) is conversion of adrenally-generated androstenedione to estrone by aromatase in peripheral tissues. Therefore, aromatase inhibition leads to a decrease in serum and tumor concentration of estrogen, leading to a decreased tumor mass or delayed progression of tumor growth in some women. Anastrozole has no detectable effect on synthesis of adrenal corticosteroids, aldosterone, and thyroid hormone.

TargetKindPharmacological actionActionsOrganismUniProt ID
AromataseProteinyes
inhibitor
HumanP11511 details
Related Articles
Absorption

Rapidly absorbed into the systemic cirulation following oral administration. Peak plasma concentrations are usually attained within 2 hours under fasting conditions, with steady-state plasma concentrations attained in approximately 7 days.

Volume of distributionNot Available
Protein binding

40%

Metabolism

Hepatic. Metabolized mainly by N-dealkylation, hydroxylation, and glucuronidation to inactive metabolites. Primary metabolite is an inactive triazole.

Route of elimination

Hepatic metabolism accounts for approximately 85% of anastrozole elimination. Renal elimination accounts for approximately 10% of total clearance.

Half life

50 hours

ClearanceNot Available
Toxicity

In rats, lethality is greater than 100 mg/kg.

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Anastrozole.Approved
BazedoxifeneThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Bazedoxifene.Approved, Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Anastrozole.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Anastrozole.Approved
ChlorotrianiseneThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Chlorotrianisene.Withdrawn
Conjugated estrogensThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Conjugated Equine Estrogens.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Anastrozole.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Anastrozole.Approved
DienestrolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Dienestrol.Approved
DiethylstilbestrolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Diethylstilbestrol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Anastrozole.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Anastrozole.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Anastrozole.Approved, Investigational
EstradiolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Estradiol.Approved, Investigational, Vet Approved
EstriolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Estriol.Approved, Vet Approved
EstroneThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Estrone.Approved
Ethinyl EstradiolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Ethinyl Estradiol.Approved
GenisteinThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Genistein.Investigational
HexestrolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Hexestrol.Withdrawn
MestranolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Mestranol.Approved
MethadoneThe serum concentration of Methadone can be increased when it is combined with Anastrozole.Approved
MethallenestrilThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Methallenestril.Experimental
OleandrinAnvirzel may decrease the cardiotoxic activities of Anastrozole.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Anastrozole.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Anastrozole.Approved, Vet Approved
QuinestrolThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Quinestrol.Approved
Synthetic Conjugated Estrogens, AThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Synthetic Conjugated Estrogens, B.Approved
TamoxifenThe serum concentration of Anastrozole can be decreased when it is combined with Tamoxifen.Approved
TiboloneThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Tibolone.Approved
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Anastrozole.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Anastrozole.Approved, Investigational
Food Interactions
  • Food decreases the rate of absorption, but the extent of absorption is not affected.
References
Synthesis Reference

Anil Khile, Narendra Joshi, Shekhar Bhirud, "Process for the preparation of anastrozole and intermediates thereof." U.S. Patent US20060189670, issued August 24, 2006.

US20060189670
General References
  1. Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, Hoctin-Boes G, Houghton J, Locker GY, Tobias JS: Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years' adjuvant treatment for breast cancer. Lancet. 2005 Jan 1-7;365(9453):60-2. [PubMed:15639680 ]
  2. Mauras N, Bishop K, Merinbaum D, Emeribe U, Agbo F, Lowe E: Pharmacokinetics and pharmacodynamics of anastrozole in pubertal boys with recent-onset gynecomastia. J Clin Endocrinol Metab. 2009 Aug;94(8):2975-8. doi: 10.1210/jc.2008-2527. Epub 2009 May 26. [PubMed:19470631 ]
  3. Nabholtz JM: Role of anastrozole across the breast cancer continuum: from advanced to early disease and prevention. Oncology. 2006;70(1):1-12. Epub 2006 Jan 26. [PubMed:16439860 ]
  4. Milani M, Jha G, Potter DA: Anastrozole Use in Early Stage Breast Cancer of Post-Menopausal Women. Clin Med Ther. 2009 Mar 31;1:141-156. [PubMed:19794821 ]
  5. Gangadhara S, Bertelli G: Long-term efficacy and safety of anastrozole for adjuvant treatment of early breast cancer in postmenopausal women. Ther Clin Risk Manag. 2009 Aug;5(4):291-300. Epub 2009 May 4. [PubMed:19753124 ]
  6. Santen RJ, Brodie H, Simpson ER, Siiteri PK, Brodie A: History of aromatase: saga of an important biological mediator and therapeutic target. Endocr Rev. 2009 Jun;30(4):343-75. doi: 10.1210/er.2008-0016. Epub 2009 Apr 23. [PubMed:19389994 ]
External Links
ATC CodesL02BG03
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelDownload (258 KB)
MSDSDownload (57.3 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0WithdrawnBasic ScienceHypertensive1
1Active Not RecruitingBasic ScienceNormal Healthy Volunteers1
1Active Not RecruitingBasic ScienceTumors, Solid1
1Active Not RecruitingTreatmentCancer, Advanced / Tumors, Solid1
1Active Not RecruitingTreatmentCancer, Breast1
1Active Not RecruitingTreatmentEstrogen Receptor Positive / Invasive Breast Carcinoma / Recurrent Breast Carcinoma / Stage IV Breast Cancer1
1CompletedNot AvailableCancer, Breast1
1CompletedNot AvailableHealthy Volunteers2
1CompletedBasic ScienceNormal Healthy Volunteers1
1CompletedDiagnosticEndometriosis1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentPharmacokinetics / Safety1
1RecruitingTreatmentBreast Cancer Triple Negative / Cancer, Ovarian / Cervical Cancers / Endometrial Cancers / Tumors, Solid1
1RecruitingTreatmentCancer, Breast / Carcinoma, Breast / Malignant Neoplasm of Breast1
1RecruitingTreatmentNeoplasms, Breast1
1RecruitingTreatmentNeoplasms / Neoplasms, Breast1
1TerminatedBasic ScienceIdiopathic Hypogonadotropic Hypogonadism / Olfacto genital dysplasia1
1, 2Active Not RecruitingTreatmentCancer, Breast1
1, 2CompletedTreatmentHealthy Males1
1, 2CompletedTreatmentRecurrent Breast Cancer / Stage IV Breast Cancer1
1, 2RecruitingTreatmentEndometrial Carcinoma / Hormone Receptor Positive Tumor / Metastatic Carcinoma1
1, 2TerminatedTreatmentCancer, Breast1
2Active Not RecruitingTreatmentBreast Cancer Invasive Nos1
2Active Not RecruitingTreatmentCancer, Breast4
2Active Not RecruitingTreatmentDCIS1
2Active Not RecruitingTreatmentEstrogen Receptor Positive / HER2/Neu Negative / Recurrent Breast Carcinoma / Stage IIA Breast Cancer / Stage IIB Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer1
2Active Not RecruitingTreatmentEstrogen Receptor-Positive Breast Cancer / HER2-Negative Breast Cancer / Progesterone Receptor-positive Breast Cancer / Recurrent Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
2Active Not RecruitingTreatmentMetastatic Breast Cancer (MBC)2
2Active Not RecruitingTreatmentPuberty, Precocious1
2CompletedPreventionHealthy Volunteers1
2CompletedTreatmentAnovulatory cycle1
2CompletedTreatmentCancer, Breast14
2CompletedTreatmentCancer, Breast / Early-Stage Breast Carcinoma / Hormone Receptor Positive Tumor1
2CompletedTreatmentCancer, Breast / Neoplasms, Breast2
2CompletedTreatmentCancer, Ovarian / Primary Peritoneal Cancer / Tubal Carcinoma1
2CompletedTreatmentBone destruction / Depressive State / Diabetes / Hypogonadism / Sarcopenia1
2CompletedTreatmentEndometriosis1
2CompletedTreatmentErectile Dysfunction (ED) / Hypogonadism / Seizures Disorders1
2CompletedTreatmentEstrogen Receptor-Positive Breast Cancer / Progesterone Receptor-positive Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer1
2CompletedTreatmentGynecomastia1
2CompletedTreatmentHypogonadism1
2CompletedTreatmentMcCune-Albright Syndrome1
2CompletedTreatmentMenstruation Disorders1
2CompletedTreatmentMetastatic Breast Cancer (MBC)2
2CompletedTreatmentPulmonary Arterial Hypertension (PAH)1
2Not Yet RecruitingTreatmentNeoplasms, Breast1
2RecruitingBasic ScienceCancer, Breast1
2RecruitingTreatmentCancer of Breast / Cancer of the Breast / Cancer, Breast / Neoplasms, Breast1
2RecruitingTreatmentCancer, Breast4
2RecruitingTreatmentCancer, Breast / Hormone Receptor Positive Tumor / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast1
2RecruitingTreatmentEarly-Stage Breast Carcinoma / Estrogen Receptor Positive Tumor1
2RecruitingTreatmentEstrogen Receptor Negative / Estrogen Receptor Positive / HER2/Neu Negative / Progesterone Receptor Negative / Progesterone Receptor Positive / Stage IV Breast Cancer / Triple-Negative Breast Carcinoma1
2RecruitingTreatmentFemale Breast Carcinoma1
2RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2RecruitingTreatmentNeoplasms, Breast2
2TerminatedTreatmentCancer of the Breast / Cancer, Breast / Neoplasms, Breast1
2TerminatedTreatmentCancer, Breast3
2TerminatedTreatmentCancer, Breast / Neoplasms / Neoplasms, Breast1
2TerminatedTreatmentEstrogen Receptor-Positive Breast Cancer / HER2-Negative Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer1
2TerminatedTreatmentEstrogen Receptor-Positive Breast Cancer / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast / Male Breast Cancer / Recurrent Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer1
2TerminatedTreatmentEstrogen Receptor-negative Breast Cancer / HER2-Negative Breast Cancer / Progesterone Receptor-negative Breast Cancer / Stage I Breast Carcinoma / Stage II Breast Cancer / Stage IIIA Breast Cancer / Triple-Negative Breast Cancer (TNBC)1
2TerminatedTreatmentMetastatic Breast Cancer (MBC)2
2TerminatedTreatmentNeoplasms, Breast2
2TerminatedTreatmentNon-Small-Cell Lung Carcinoma (NSCLC) / Postmenopausal Women1
2Unknown StatusTreatmentCancer, Breast4
2Unknown StatusTreatmentMetastatic Breast Cancer (MBC)1
2WithdrawnBasic SciencePost-menopausal ER+ Stage I-IIIA Primary Operable Breast Cancer1
2WithdrawnTreatmentBreast Cancer Metastatic1
2WithdrawnTreatmentCancer, Breast2
2WithdrawnTreatmentMetabolic Syndromes1
2, 3CompletedNot AvailableHypopituitarism1
3Active Not RecruitingPreventionCancer, Breast1
3Active Not RecruitingTreatmentAdvanced, Metastatic Breast Cancer1
3Active Not RecruitingTreatmentBreast Adenocarcinoma / Estrogen Receptor and/or Progesterone Receptor Positive / HER2/Neu Negative / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage IIA Breast Cancer / Stage IIB Breast Cancer / Stage IIIB Breast Cancer1
3Active Not RecruitingTreatmentCancer, Breast7
3Active Not RecruitingTreatmentHormone Receptor Positive Breast Cancer1
3CompletedNot AvailableBone Density1
3CompletedNot AvailableCancer, Breast1
3CompletedNot AvailableQuality of Life1
3CompletedTreatmentAdvanced Breast Cancer2
3CompletedTreatmentCancer, Breast12
3CompletedTreatmentGynecomastia1
3CompletedTreatmentIdiopathic Short Stature (ISS)1
3CompletedTreatmentNeoplasms, Breast2
3CompletedTreatmentProgression-free Survival1
3Not Yet RecruitingTreatmentCancer, Breast1
3RecruitingTreatmentBreast Cancer Metastatic1
3RecruitingTreatmentCancer, Breast5
3RecruitingTreatmentDuctal Breast Carcinoma In Situ / Estrogen Receptor and/or Progesterone Receptor Positive / HER2/Neu Negative / Invasive Breast Carcinoma / Multicentric Breast Carcinoma / Multifocal Breast Carcinoma / Synchronous Bilateral Breast Carcinoma1
3RecruitingTreatmentEstrogen Receptor Positive Breast Cancer / HER-2 Positive Breast Cancer1
3RecruitingTreatmentEstrogen Receptor-Positive Breast Cancer / HER2-Negative Breast Cancer / Invasive Ductal Breast Carcinoma / Invasive Lobular Breast Carcinoma / Recurrent Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer1
3RecruitingTreatmentMetastatic Breast Cancer (MBC)1
3TerminatedTreatmentBMI >30 kg/m2 / Oligozoospermia1
3TerminatedTreatmentCancer, Breast2
3Unknown StatusTreatmentCancer, Breast7
4Active Not RecruitingTreatmentHormono-depending Adjuvant Breast Cancer1
4CompletedHealth Services ResearchCancer, Breast1
4CompletedTreatmentCancer, Breast3
4CompletedTreatmentStage I Breast Carcinoma1
4RecruitingTreatmentFemale Breast Cancer1
4RecruitingTreatmentHypogonadism / Obesity, Severe1
4RecruitingTreatmentShort Stature1
4Unknown StatusNot AvailableArthralgia1
4Unknown StatusTreatmentCancer, Breast1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast1
Not AvailableActive Not RecruitingTreatmentMale Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer2
Not AvailableActive Not RecruitingTreatmentPrader-Willi Syndrome / Silver Russell Syndrome1
Not AvailableCompletedNot AvailableAdvanced Breast Cancer1
Not AvailableCompletedNot AvailableArthralgia / BMI >30 kg/m2 / Cancer, Breast1
Not AvailableCompletedNot AvailableArthralgia / Cancer, Breast / Pain1
Not AvailableCompletedNot AvailableArthralgia / Post Menopausal1
Not AvailableCompletedNot AvailableCancer, Breast4
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Menopausal Syndromes1
Not AvailableCompletedBasic ScienceCancer, Breast2
Not AvailableCompletedTreatmentBreast Cancer Invasive Nos1
Not AvailableCompletedTreatmentCancer, Breast4
Not AvailableEnrolling by InvitationNot AvailableCancer, Breast1
Not AvailableRecruitingNot AvailableHypogonadism1
Not AvailableRecruitingDiagnosticHealthy Volunteers1
Not AvailableRecruitingSupportive CareEstrogen Receptor-Positive Breast Cancer / Musculoskeletal Complications / Progesterone Receptor-positive Breast Cancer / Recurrent Breast Cancer / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer1
Not AvailableRecruitingTreatmentCancer, Breast2
Not AvailableSuspendedTreatmentMetabolic Syndromes1
Not AvailableTerminatedNot AvailableCancer, Breast1
Not AvailableUnknown StatusTreatmentMetabolic Syndromes1
Not AvailableWithdrawnOtherHypertensive1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral1 mg/1
Tablet, coatedOral1 mg/1
Tablet, film coatedOral1 mg/1
TabletOral1 mg
Prices
Unit descriptionCostUnit
Anastrozole 100% powder1326.52USD g
Arimidex 1 mg tablet15.3USD tablet
Aromasin 25 mg tablet14.04USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1337420 No1995-10-242012-10-24Canada
USRE36617 No1993-06-272010-06-27Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)130.14 °CNot Available
water solubility0.5 mg/mLNot Available
logP2.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0661 mg/mLALOGPS
logP2.31ALOGPS
logP3.03ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)2.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.29 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.47 m3·mol-1ChemAxon
Polarizability31.97 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9965
Blood Brain Barrier+0.9382
Caco-2 permeable+0.5516
P-glycoprotein substrateNon-substrate0.6405
P-glycoprotein inhibitor INon-inhibitor0.764
P-glycoprotein inhibitor IINon-inhibitor0.7662
Renal organic cation transporterNon-inhibitor0.512
CYP450 2C9 substrateNon-substrate0.803
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5761
CYP450 1A2 substrateNon-inhibitor0.6218
CYP450 2C9 inhibitorNon-inhibitor0.7616
CYP450 2D6 inhibitorNon-inhibitor0.9183
CYP450 2C19 inhibitorNon-inhibitor0.6404
CYP450 3A4 inhibitorNon-inhibitor0.6501
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7038
Ames testNon AMES toxic0.6394
CarcinogenicityNon-carcinogens0.8068
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5564 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9464
hERG inhibition (predictor II)Non-inhibitor0.8878
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004l-1390000000-8636c0aef7d79b805328View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0090000000-8ccdc5fa9f18334eae92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative ParentsTriazoles / Heteroaromatic compounds / Nitriles / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
SubstituentsPhenylpropane / Heteroaromatic compound / 1,2,4-triazole / Azole / Azacycle / Organoheterocyclic compound / Nitrile / Carbonitrile / Organic nitrogen compound / Organopnictogen compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorsnitrile, triazoles (CHEBI:2704 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Mauras N, Bishop K, Merinbaum D, Emeribe U, Agbo F, Lowe E: Pharmacokinetics and pharmacodynamics of anastrozole in pubertal boys with recent-onset gynecomastia. J Clin Endocrinol Metab. 2009 Aug;94(8):2975-8. doi: 10.1210/jc.2008-2527. Epub 2009 May 26. [PubMed:19470631 ]
  3. Nabholtz JM: Role of anastrozole across the breast cancer continuum: from advanced to early disease and prevention. Oncology. 2006;70(1):1-12. Epub 2006 Jan 26. [PubMed:16439860 ]
  4. Jakesz R, Greil R, Gnant M, Schmid M, Kwasny W, Kubista E, Mlineritsch B, Tausch C, Stierer M, Hofbauer F, Renner K, Dadak C, Rucklinger E, Samonigg H: Extended adjuvant therapy with anastrozole among postmenopausal breast cancer patients: results from the randomized Austrian Breast and Colorectal Cancer Study Group Trial 6a. J Natl Cancer Inst. 2007 Dec 19;99(24):1845-53. Epub 2007 Dec 11. [PubMed:18073378 ]
  5. Cuzick J: Anastrozole. Drugs Today (Barc). 2005 Apr;41(4):227-39. [PubMed:16034487 ]
  6. Rugo HS: The breast cancer continuum in hormone-receptor-positive breast cancer in postmenopausal women: evolving management options focusing on aromatase inhibitors. Ann Oncol. 2008 Jan;19(1):16-27. Epub 2007 Aug 9. [PubMed:17693420 ]
  7. Milani M, Jha G, Potter DA: Anastrozole Use in Early Stage Breast Cancer of Post-Menopausal Women. Clin Med Ther. 2009 Mar 31;1:141-156. [PubMed:19794821 ]
  8. Gangadhara S, Bertelli G: Long-term efficacy and safety of anastrozole for adjuvant treatment of early breast cancer in postmenopausal women. Ther Clin Risk Manag. 2009 Aug;5(4):291-300. Epub 2009 May 4. [PubMed:19753124 ]
  9. Santen RJ, Brodie H, Simpson ER, Siiteri PK, Brodie A: History of aromatase: saga of an important biological mediator and therapeutic target. Endocr Rev. 2009 Jun;30(4):343-75. doi: 10.1210/er.2008-0016. Epub 2009 Apr 23. [PubMed:19389994 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Drug created on June 13, 2005 07:24 / Updated on June 24, 2017 13:16