Identification

Name
Anastrozole
Accession Number
DB01217  (APRD00016)
Type
Small Molecule
Groups
Approved, 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 Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act AnastrozoleTablet1 mgOralActavis Pharma Company2012-10-25Not applicableCanada
AnastrozoleTablet1 mgOralSanis Health Inc2015-07-22Not applicableCanada
AnastrozoleTablet1 mgOralPro Doc Limitee2012-11-22Not applicableCanada
AnastrozoleTablet, film coated1 mg/1OralGlobal Pharmaceuticals2013-06-052013-08-26Us
ArimidexTablet1 mg/1OralANI Pharmaceuticals, Inc.2018-06-26Not applicableUs
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
Sandoz AnastrozoleTablet1 mgOralSandoz Canada Incorporated2012-07-26Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-anastrozole TabletsTablet1 mgOralAccel Pharma IncNot applicableNot applicableCanada
Ach-anastrozoleTablet1 mgOralAccord Healthcare Limited2012-10-25Not applicableCanada
AnastrozoleTablet, film coated1 mg/1OralGolden State Medical Supply2013-01-08Not applicableUs
AnastrozoleTablet, coated1 mg/1OralAv Kare, Inc.2010-06-282011-12-12Us
AnastrozoleTablet, film coated1 mg/1Oralbryant ranch prepack2012-05-31Not applicableUs
AnastrozoleTablet1 mg/1OralA-S Medication Solutions2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralAPP Pharmaceuticals, Inc.2010-06-28Not applicableUs
AnastrozoleTablet1 mg/1OralAscend Laboratories, LLC2010-06-28Not applicableUs
AnastrozoleTablet, film coated1 mg/1OralMylan Institutional2010-06-112013-09-30Us
AnastrozoleTablet1 mg/1OralStason Pharmaceuticals, Inc.2017-04-10Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Testosterone / AnastrozoleAnastrozole (20 mg/1) + Testosterone (200 mg/1)PelletOralQualgen Llc2017-11-14Not applicableUs
International/Other Brands
Anastrole
Categories
UNII
2Z07MYW1AZ
CAS number
120511-73-1
Weight
Average: 293.3663
Monoisotopic: 293.164045633
Chemical Formula
C17H19N5
InChI Key
YBBLVLTVTVSKRW-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.

Associated Conditions
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.

TargetActionsOrganism
ACytochrome P450 19A1
inhibitor
Human
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 distribution
Not 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

Clearance
Not Available
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Anastrozole.
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Anastrozole.
AlclometasoneThe metabolism of Alclometasone can be decreased when combined with Anastrozole.
AlfuzosinThe metabolism of Alfuzosin can be decreased when combined with Anastrozole.
AmcinonideThe metabolism of Amcinonide can be decreased when combined with Anastrozole.
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Anastrozole.
AmsacrineThe risk or severity of cardiotoxicity can be increased when Anastrozole is combined with Amsacrine.
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Anastrozole.
AzithromycinThe metabolism of Azithromycin can be decreased when combined with Anastrozole.
BevacizumabThe risk or severity of cardiotoxicity can be increased when Bevacizumab is combined with Anastrozole.
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
Human Metabolome Database
HMDB0015348
KEGG Drug
D00960
KEGG Compound
C08159
PubChem Compound
2187
PubChem Substance
46504987
ChemSpider
2102
BindingDB
10015
ChEBI
2704
ChEMBL
CHEMBL1399
Therapeutic Targets Database
DAP000627
PharmGKB
PA448432
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Anastrozole
ATC Codes
L02BG03 — Anastrozole
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (258 KB)
MSDS
Download (57.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0WithdrawnBasic ScienceHigh Blood Pressure (Hypertension)1
1Active Not RecruitingBasic ScienceNormal Healthy Volunteers1
1Active Not RecruitingBasic ScienceTumors, Solid1
1Active Not RecruitingTreatmentCancer, Advanced / Tumors, Solid1
1CompletedNot AvailableCancer, Breast1
1CompletedNot AvailableHealthy Volunteers2
1CompletedBasic ScienceNormal Healthy Volunteers1
1CompletedDiagnosticEndometriosis1
1CompletedPreventionMammographic Density1
1CompletedTreatmentCancer, Breast1
1CompletedTreatmentEstrogen Receptor Positive / Invasive Breast Carcinoma / Recurrent Breast Carcinoma / Stage IV Breast Cancer / Stage IV Breast Cancer AJCC v6 and v71
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentMammographic Density1
1CompletedTreatmentPharmacokinetics / Safety1
1Not Yet RecruitingTreatmentAnatomic Stage III Breast Cancer AJCC v8 / Anatomic Stage IIIA Breast Cancer AJCC v8 / Anatomic Stage IIIB Breast Cancer AJCC v8 / Anatomic Stage IIIC Breast Cancer AJCC v8 / Anatomic Stage IV Breast Cancer AJCC v8 / Estrogen Receptor Positive / HER2/Neu Negative / Invasive Breast Carcinoma / Prognostic Stage III Breast Cancer AJCC v8 / Prognostic Stage IIIA Breast Cancer AJCC v8 / Prognostic Stage IIIB Breast Cancer AJCC v8 / Prognostic Stage IIIC Breast Cancer AJCC v8 / Prognostic Stage IV Breast Cancer AJCC v8 / Recurrent Breast Carcinoma1
1RecruitingTreatmentBreast Cancer Triple Negative / Cancer of the Ovary / 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, 2CompletedTreatmentCancer, Breast1
1, 2CompletedTreatmentHealthy Males1
1, 2CompletedTreatmentRecurrent Breast Cancer / Stage IV Breast Cancer1
1, 2RecruitingTreatmentBreast Diseases / Neoplasms, Breast1
1, 2RecruitingTreatmentEndometrial Carcinoma / Hormone Receptor Positive Tumor / Metastatic Carcinoma1
1, 2TerminatedTreatmentCancer, Breast1
2Active Not RecruitingTreatmentBreast Cancer Invasive Nos1
2Active Not RecruitingTreatmentCancer, Breast5
2Active Not RecruitingTreatmentDCIS1
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
2CompletedPreventionHealthy Volunteers1
2CompletedTreatmentAnovulatory cycle1
2CompletedTreatmentCancer of the Ovary / Primary Peritoneal Cancer / Tubal Carcinoma1
2CompletedTreatmentCancer, Breast15
2CompletedTreatmentCancer, Breast / Early-Stage Breast Carcinoma / Hormone Receptor Positive Tumor1
2CompletedTreatmentCancer, Breast / Neoplasms, Breast2
2CompletedTreatmentBone destruction / Depression / Diabetes Mellitus (DM) / 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
2CompletedTreatmentPuberty, Precocious1
2CompletedTreatmentPulmonary Arterial Hypertension (PAH)1
2Not Yet RecruitingOtherCancer, Breast1
2Not Yet RecruitingTreatmentLow Grade Endometrial Stromal Sarcoma1
2RecruitingBasic ScienceCancer, Breast1
2RecruitingTreatmentBreast Cancer Invasive Nos / Cancer, Breast1
2RecruitingTreatmentBreast Cancer Metastatic1
2RecruitingTreatmentCancer of the Breast / Cancer, Breast / Neoplasms, Breast1
2RecruitingTreatmentCancer, Breast2
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, Breast4
2RecruitingTreatmentPulmonary Arterial Hypertension (PAH)1
2TerminatedTreatmentCancer of the Breast / Cancer, Breast / Neoplasms, Breast1
2TerminatedTreatmentCancer, Breast3
2TerminatedTreatmentCancer, Breast / Neoplasms / Neoplasms, Breast1
2TerminatedTreatmentEstrogen 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
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
2TerminatedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Postmenopausal Women1
2TerminatedTreatmentMetastatic Breast Cancer (MBC)2
2TerminatedTreatmentNeoplasms, Breast2
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 Cancer / Advanced, Metastatic Breast Cancer1
3Active Not RecruitingTreatmentBreast Adenocarcinoma / Estrogen Receptor and/or Progesterone Receptor Positive / HER2/Neu Negative / Stage IA Breast Cancer / Stage IA Breast Cancer AJCC v7 / Stage IB Breast Cancer / Stage IB Breast Cancer AJCC v7 / Stage IIA Breast Cancer / Stage IIA Breast Cancer AJCC v6 and v7 / Stage IIB Breast Cancer / Stage IIB Breast Cancer AJCC v6 and v7 / Stage IIIB Breast Cancer / Stage IIIB Breast Cancer AJCC v71
3Active Not RecruitingTreatmentBreast Cancer Metastatic1
3Active Not RecruitingTreatmentCancer, Breast8
3Active Not RecruitingTreatmentDuctal 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
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
3RecruitingTreatmentBreast Neoplasm Female1
3RecruitingTreatmentCancer, Breast6
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
3SuspendedTreatmentCancer, Breast1
3TerminatedTreatmentBMI >30 kg/m2 / Oligozoospermia1
3TerminatedTreatmentCancer, Breast2
3Unknown StatusTreatmentCancer, Breast5
4CompletedHealth Services ResearchCancer, Breast1
4CompletedTreatmentCancer, Breast4
4CompletedTreatmentHormono-depending Adjuvant Breast Cancer1
4CompletedTreatmentStage I Breast Carcinoma1
4Not Yet RecruitingTreatmentHER2/Neu Negative / Invasive Breast Carcinoma / One to five years postmenopausal / Stage 0 Breast Cancer / Stage IA Breast Cancer1
4RecruitingTreatmentBMI >30 kg/m2 / Hypogonadism, Hypogonadotropic1
4RecruitingTreatmentFemale Breast Cancer1
4RecruitingTreatmentHypogonadism / Obesity, Severe1
4RecruitingTreatmentNeoplasms, Breast1
4RecruitingTreatmentShort Stature1
4Unknown StatusNot AvailableArthralgia/joint pain1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast1
Not AvailableActive Not RecruitingTreatmentMale Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer1
Not AvailableActive Not RecruitingTreatmentPrader-Willi Syndrome / Silver Russell Syndrome1
Not AvailableCompletedNot AvailableAdvanced Breast Cancer1
Not AvailableCompletedNot AvailableArthralgia/joint pain / BMI >30 kg/m2 / Cancer, Breast1
Not AvailableCompletedNot AvailableCancer, Breast4
Not AvailableCompletedNot AvailableArthralgia/joint pain / Cancer, Breast / Pain1
Not AvailableCompletedNot AvailableArthralgia/joint pain / Post Menopausal1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Menopausal Syndromes1
Not AvailableCompletedBasic ScienceCancer, Breast2
Not AvailableCompletedDiagnosticHealthy Volunteers1
Not AvailableCompletedTreatmentBreast Cancer Invasive Nos1
Not AvailableCompletedTreatmentCancer, Breast4
Not AvailableCompletedTreatmentMale Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer1
Not AvailableEnrolling by InvitationNot AvailableCancer, Breast1
Not AvailableRecruitingOtherHypogonadism1
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 AvailableWithdrawnOtherHigh Blood Pressure (Hypertension)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Accord Healthcare
  • Ascend Laboratories LLC
  • AstraZeneca Inc.
  • Breckenridge Pharmaceuticals
  • Cadila Healthcare Ltd.
  • Cypress Pharmaceutical Inc.
  • Doctor Reddys Laboratories Ltd.
  • Kaiser Foundation Hospital
  • Karalex Pharmaceuticals
  • Lake Erie Medical and Surgical Supply
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Physicians Total Care Inc.
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandoz
  • Teva Pharmaceutical Industries Ltd.
  • Three Rivers Pharmaceuticals LLC
  • UDL Laboratories
  • Zeneca Pharma Inc.
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral1 mg/1
Tablet, coatedOral1 mg/1
Tablet, film coatedOral1 mg/1
TabletOral1 mg
PelletOral
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)
USRE36617No1993-06-272010-06-27Us
CA1337420No1995-10-242012-10-24Canada

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004l-1390000000-8636c0aef7d79b805328
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004l-0190000000-739ac0c546bb150b1c60
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0090000000-8ccdc5fa9f18334eae92

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Triazoles / Heteroaromatic compounds / Nitriles / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenylpropane / Heteroaromatic compound / 1,2,4-triazole / Azole / Azacycle / Organoheterocyclic compound / Nitrile / Carbonitrile / Organic nitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
nitrile, triazoles (CHEBI:2704)

Targets

Details
1. Cytochrome P450 19A1
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
Uniprot Name
Aromatase
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
Uniprot Name
Aromatase
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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]
  2. Grimm SW, Dyroff MC: Inhibition of human drug metabolizing cytochromes P450 by anastrozole, a potent and selective inhibitor of aromatase. Drug Metab Dispos. 1997 May;25(5):598-602. [PubMed:9152599]

Drug created on June 13, 2005 07:24 / Updated on September 21, 2018 20:42