Identification

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Name
Exemestane
Accession Number
DB00990  (APRD00144)
Type
Small Molecule
Groups
Approved, Investigational
Description

Exemestane is an oral steroidal aromatase inhibitor used in the adjuvant treatment of hormonally-responsive (also called hormone-receptor-positive, estrogen-responsive) breast cancer in postmenopausal women. It irreversibly binds to the active site of the enzyme resulting in permanent inhibition.

Structure
Thumb
Synonyms
  • 6-methyleneandrosta-1,4-diene-3,17-dione
  • Exemestane
  • Exemestano
  • Exemestanum
External IDs
FCE-24304 / FCE24304 / PNU-155971
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act ExemestaneTabletOralActavis Pharma Company2012-07-26Not applicableCanada
AromasinTablet25 mgOralPfizer Canada Ulc2000-08-17Not applicableCanada
AromasinTablet25 mg/1OralPharmacia & Upjohn Inc1999-10-21Not applicableUs00009 7663 04 nlmimage10 fd12fea7
AromasinTablet25 mg/1OralPhysicians Total Care, Inc.2005-06-29Not applicableUs54868 526120180907 15195 1wlbazh
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-exemestaneTabletOralApotex Corporation2014-05-01Not applicableCanada
ExemestaneTablet25 mg/1OralZydus Pharmaceuticals (USA) Inc.2018-10-08Not applicableUs
ExemestaneTablet25 mg/1OralCadila Healthcare Limited2018-10-08Not applicableUs
ExemestaneTablet, film coated25 mg/1OralWest-Ward Pharmaceuticals Corp2011-04-01Not applicableUs
ExemestaneTablet25 mg/1OralUpsher Smith Laboratories2017-07-27Not applicableUs
ExemestaneTablet, film coated25 mg/1OralAmneal Pharmaceuticals LLC2018-12-29Not applicableUs
ExemestaneTablet, sugar coated25 mg/1OralGreenstone, Llc2011-04-01Not applicableUs59762 2858 01 nlmimage10 00200070
ExemestaneTablet25 mg/1OralAlvogen Inc.2014-07-25Not applicableUs47781 0108 30 nlmimage10 ee3df73f
ExemestaneTablet25 mg/1OralCipla USA Inc.2018-04-27Not applicableUs
ExemestaneTablet25 mg/1OralAmerincan Health Packaging2015-03-312017-04-30Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Exemestance
Categories
UNII
NY22HMQ4BX
CAS number
107868-30-4
Weight
Average: 296.4034
Monoisotopic: 296.177630012
Chemical Formula
C20H24O2
InChI Key
BFYIZQONLCFLEV-DAELLWKTSA-N
InChI
InChI=1S/C20H24O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h6,8,11,14-16H,1,4-5,7,9-10H2,2-3H3/t14-,15-,16-,19+,20-/m0/s1
IUPAC Name
(1S,2R,10R,11S,15S)-2,15-dimethyl-8-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,14-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC(=C)C2=CC(=O)C=C[C@]12C

Pharmacology

Indication

For the treatment of advanced breast cancer in postmenopausal women whose disease has progressed following tamoxifen therapy.

Associated Conditions
Pharmacodynamics

Aromatase is an enzyme that converts hormones to estrogen in the body's adrenal glands. The aromatase inhibitors (AIs) are drugs that reduce estrogen levels by blocking the action of aromatase in the adrenal glands. The selective AIs (SAIs) selectively reduce levels of estrogen without interfering with levels of other steroid hormones that are produced by the adrenal gland. Drugs in this class include anastrozole (Arimidex ™), letrozole (Femara ™) and exemestane (Aromasin ™).

Mechanism of action

Breast cancer cell growth may be estrogen-dependent. Aromatase (exemestane) is the principal enzyme that converts androgens to estrogens both in pre- and postmenopausal women. While the main source of estrogen (primarily estradiol) is the ovary in premenopausal women, the principal source of circulating estrogens in postmenopausal women is from conversion of adrenal and ovarian androgens (androstenedione and testosterone) to estrogens (estrone and estradiol) by the aromatase enzyme in peripheral tissues. Estrogen deprivation through aromatase inhibition is an effective and selective treatment for some postmenopausal patients with hormone-dependent breast cancer. Exemestane is an irreversible, steroidal aromatase inactivator, structurally related to the natural substrate androstenedione. It irreversibly binds to the active site causing permanent inhibition necessitating de novo synthesis to restore enzymatic function. Exemestane significantly lowers circulating estrogen concentrations in postmenopausal women, but has no detectable effect on the adrenal biosynthesis of corticosteroids or aldosterone. This reduction in serum and tumor concentrations of estrogen delays tumor growth and disease progression. Exemestane has no effect on other enzymes involved in the steroidogenic pathway up to a concentration at least 600 times higher than that inhibiting the aromatase enzyme.

TargetActionsOrganism
ACytochrome P450 19A1
inhibitor
Humans
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

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Absorption

42%

Volume of distribution
Not Available
Protein binding

90% (mainly α1-acid glycoprotein and albumin)

Metabolism

Hepatic

Route of elimination
Not Available
Half life

24 hours

Clearance
Not Available
Toxicity

Convulsions

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
ApalutamideThe metabolism of Exemestane can be increased when combined with Apalutamide.
Biochanin AThe therapeutic efficacy of Exemestane can be decreased when used in combination with Biochanin A.
CarbamazepineThe metabolism of Exemestane can be increased when combined with Carbamazepine.
ChlorotrianiseneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Chlorotrianisene.
Conjugated estrogensThe therapeutic efficacy of Exemestane can be decreased when used in combination with Conjugated estrogens.
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Exemestane.
DexamethasoneThe metabolism of Exemestane can be increased when combined with Dexamethasone.
DienestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Dienestrol.
DiethylstilbestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Diethylstilbestrol.
EnzalutamideThe metabolism of Exemestane can be increased when combined with Enzalutamide.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • High-fat meals increase plasma exemestane concentrations by approximately 40%.

References

Synthesis Reference

Kevin Kunnen, Nathan W. Stehle, Scot W. Weis, John M. Pascone, Richard J. Pariza, Scott G. Van Ornum, Paul Zizelman, "Exemestane and Its Intermediates and Methods of Making the Same." U.S. Patent US20080234505, issued September 25, 2008.

US20080234505
General References
  1. Coombes RC, Kilburn LS, Snowdon CF, Paridaens R, Coleman RE, Jones SE, Jassem J, Van de Velde CJ, Delozier T, Alvarez I, Del Mastro L, Ortmann O, Diedrich K, Coates AS, Bajetta E, Holmberg SB, Dodwell D, Mickiewicz E, Andersen J, Lonning PE, Cocconi G, Forbes J, Castiglione M, Stuart N, Stewart A, Fallowfield LJ, Bertelli G, Hall E, Bogle RG, Carpentieri M, Colajori E, Subar M, Ireland E, Bliss JM: Survival and safety of exemestane versus tamoxifen after 2-3 years' tamoxifen treatment (Intergroup Exemestane Study): a randomised controlled trial. Lancet. 2007 Feb 17;369(9561):559-70. [PubMed:17307102]
  2. Robinson A: A review of the use of exemestane in early breast cancer. Ther Clin Risk Manag. 2009 Feb;5(1):91-8. Epub 2009 Mar 26. [PubMed:19436613]
  3. Untch M, Jackisch C: Exemestane in early breast cancer: a review. Ther Clin Risk Manag. 2008 Dec;4(6):1295-304. [PubMed:19337436]
  4. Abrial C, Durando X, Mouret-Reynier MA, Thivat E, Bayet-Robert M, Nayl B, Dubray P, Pomel C, Chollet P, Penault-Llorca F: Role of neo-adjuvant hormonal therapy in the treatment of breast cancer: a review of clinical trials. Int J Gen Med. 2009 Jul 30;2:129-40. [PubMed:20360896]
  5. Nabholtz JM: Long-term safety of aromatase inhibitors in the treatment of breast cancer. Ther Clin Risk Manag. 2008 Feb;4(1):189-204. [PubMed:18728707]
External Links
Human Metabolome Database
HMDB0015125
KEGG Drug
D00963
KEGG Compound
C08162
PubChem Compound
60198
PubChem Substance
46508243
ChemSpider
54278
BindingDB
50398447
ChEBI
4953
ChEMBL
CHEMBL1200374
Therapeutic Targets Database
DAP000625
PharmGKB
PA449563
HET
EXM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Exemestane
ATC Codes
L02BG06 — Exemestane
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
PDB Entries
3s7s
FDA label
Download (74.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentBreast Cancer2
1Active Not RecruitingTreatmentBreast Cancer / Estrogen Receptor Positive Breast Cancer1
1Active Not RecruitingTreatmentMetastatic or Locally-advanced Unresectable Breast Cancer1
1Active Not RecruitingTreatmentNeoplasms1
1CompletedTreatmentBreast Cancer3
1CompletedTreatmentBreast Cancer / Estrogen Receptor Breast Cancer / Lung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancers1
1CompletedTreatmentMalignant Lymphomas / Tumors, Solid1
1CompletedTreatmentNeoplasms1
1CompletedTreatmentNeoplasms / Neoplasms, Breast / Neoplasms, Kidney / Pancreatic Neuroendocine Neoplasms1
1CompletedTreatmentStage IV Non-Small Cell Lung Cancer1
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
1RecruitingTreatmentAdvanced Breast Cancer1
1RecruitingTreatmentBreast Cancer1
1RecruitingTreatmentNeoplasms, Breast1
1TerminatedTreatmentAdvanced Estrogen Receptor Positive HER2- Breast Cancer1
1TerminatedTreatmentEstrogen Receptor Positive / HER2/Neu Negative / Male Breast Carcinoma / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
1WithdrawnBasic ScienceHealthy Volunteers1
1WithdrawnTreatmentMetastatic Breast Cancer1
1, 2Active Not RecruitingTreatmentBreast Cancer1
1, 2CompletedTreatmentER+ Breast Cancer / FGFR Inhibition, Pharmacokinetics, Biomarkers1
1, 2RecruitingTreatmentHormone Receptor (HR)-Positive Breast Cancer / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast1
1, 2RecruitingTreatmentNeoplasms, Breast1
1, 2RecruitingTreatmentPremenopausal Breast Cancer1
1, 2TerminatedTreatmentBreast Cancer1
1, 2TerminatedTreatmentMetastatic Breast Cancer1
1, 2TerminatedTreatmentNeoplasms, Breast1
1, 2Unknown StatusTreatmentBreast Cancer1
2Active Not RecruitingPreventionEarly Breast Cancer / Estrogen Receptor Positive / One to five years postmenopausal / Stage 0 Breast Cancer / Stage 0 Breast Cancer AJCC v6 and v7 / Stage I Breast Cancer AJCC v7 / Stage IA Breast Cancer / Stage IA Breast Cancer AJCC v7 / Stage IB Breast Cancer / Stage IB Breast Cancer AJCC v7 / Stage II Breast Cancer / Stage II Breast Cancer AJCC v6 and v7 / Stage IIA Breast Cancer / Stage IIA Breast Cancer AJCC v6 and v7 / Stage IIB Breast Cancer / Stage IIB Breast Cancer AJCC v6 and v71
2Active Not RecruitingTreatmentAdvanced or Recurrent Breast Cancer1
2Active Not RecruitingTreatmentBreast Cancer4
2Active Not RecruitingTreatmentBreast Cancer / Hormone Receptor Positive Tumor / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast1
2Active Not RecruitingTreatmentBreast Cancer / Stage II Breast Cancer / Stage III Breast Cancer1
2Active Not RecruitingTreatmentHormone Receptor Positive Breast Cancer1
2Active Not RecruitingTreatmentMetastatic Breast Cancer2
2Active Not RecruitingTreatmentNeoplasms, Breast3
2Active Not RecruitingTreatmentPrimary Breast Cancer AR+ve TNBN / Primary Breast Cancer ER+ve1
2CompletedPreventionAdvanced Breast Cancer1
2CompletedPreventionNeoplasms, Breast1
2CompletedTreatmentBreast Cancer12
2CompletedTreatmentBreast Cancer / Breast Cancer, Estrogen Receptor-Positive / ER+ Breast Cancer / Estrogen Receptor-Positive Breast Cancer1
2CompletedTreatmentEndometrial Cancer1
2CompletedTreatmentEstrogen-receptor Positive Invasive Metastatic Breast Cancer1
2CompletedTreatmentHer2 Negative Breast Cancer Patients1
2CompletedTreatmentMetastatic Beast Cancer1
2CompletedTreatmentMetastatic Breast Cancer3
2CompletedTreatmentMetastatic ER+ Her2- Breast Cancer / One to five years postmenopausal1
2CompletedTreatmentNeoplasms, Breast4
2CompletedTreatmentOvarian Cancer1
2CompletedTreatmentProstate Cancer1
2Not Yet RecruitingTreatmentBreast Diseases / Her2-Positive Breast Cancer / Hormone Receptor Positive Malignant Neoplasm of Breast / Hormone Receptor Positive Tumor / Malignant Neoplasm of Female Breast / Metastatic Breast Cancer2
2RecruitingBasic ScienceBreast Cancer1
2RecruitingTreatmentAdvanced Breast Cancer1
2RecruitingTreatmentAnatomic Stage IV Breast Cancer AJCC v8 / Estrogen Receptor Positive / HER2/Neu Negative / Metastatic Breast Carcinoma / Metastatic Malignant Neoplasm in the Bone / Progesterone Receptor Positive / Prognostic Stage IV Breast Cancer AJCC v81
2RecruitingTreatmentAtypical Hyperplasia / Endometrial Intraepithelial Neoplasia / FIGO Grade 1 Endometrial Endometrioid Adenocarcinoma / FIGO Grade 2 Endometrial Endometrioid Adenocarcinoma / Grade 1 Endometrial Endometrioid Adenocarcinoma / Grade 2 Endometrial Endometrioid Adenocarcinoma / One to five years postmenopausal1
2RecruitingTreatmentBreast Cancer4
2RecruitingTreatmentBreast Cancer / Cancer of the Breast / Neoplasms, Breast1
2RecruitingTreatmentBreast Cancer / Hormone Receptor Positive Tumor1
2RecruitingTreatmentBreast Cancer / Invasive Breast Cancer1
2RecruitingTreatmentEarly-Stage Breast Carcinoma / Estrogen Receptor Positive Tumor1
2RecruitingTreatmentEarly-Stage Breast Carcinoma / Hormone 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
2RecruitingTreatmentLow Grade Endometrial Stromal Sarcoma1
2RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2RecruitingTreatmentMetastatic Breast Cancer4
2RecruitingTreatmentNeoplasms, Breast3
2TerminatedTreatmentAdvanced Breast Cancer1
2TerminatedTreatmentBreast Cancer3
2TerminatedTreatmentEarly Breast Cancer / Estrogen Receptor-Positive Breast Cancer / HER2-Negative Breast Cancer / Progesterone Receptor-positive Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer1
2TerminatedTreatmentNeoplasms, Breast2
2Unknown StatusPreventionNeoplasms, Breast1
2Unknown StatusTreatmentBreast Cancer1
2Unknown StatusTreatmentHormone Receptor Positive Malignant Neoplasm of Breast1
2WithdrawnTreatmentBreast Cancer3
2WithdrawnTreatmentHormone-receptors Positive Breast Cancer1
2WithdrawnTreatmentMetastatic Breast Cancer1
2WithdrawnTreatmentNeoplasms, Breast1
2WithdrawnTreatmentStage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer1
2, 3Not Yet RecruitingTreatmentBreast Cancer1
2, 3TerminatedTreatmentBreast Cancer1
2, 3Unknown StatusTreatmentBreast Cancer1
3Active Not RecruitingTreatmentBreast Adenocarcinoma / Estrogen Receptor Positive / HER2/Neu Negative / Locally Advanced Breast Carcinoma / Male Breast Carcinoma / Metastatic Breast Carcinoma / Progesterone Receptor Positive / Recurrent Breast Carcinoma / Stage III Breast Cancer AJCC V7 / Stage IIIA Breast Cancer AJCC v7 / Stage IIIB Breast Cancer / Stage IIIB Breast Cancer AJCC v7 / Stage IIIC Breast Cancer / Stage IIIC Breast Cancer AJCC v7 / Stage IV Breast Cancer / Stage IV Breast Cancer AJCC v6 and v71
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 Cancer5
3Active Not RecruitingTreatmentBreast Cancer / Estrogen Receptor Positive Breast Cancer / Progesterone Receptor Positive Tumor / Recurrent Breast Carcinoma / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage IIA Breast Cancer / Stage IIB Breast Cancer / Stage IIIA Breast Cancer1
3Active Not RecruitingTreatmentDuctal Breast Carcinoma In Situ / Estrogen Receptor and/or Progesterone Receptor Positive / Estrogen Receptor Positive / HER2/Neu Negative / Invasive Breast Carcinoma / Multicentric Breast Carcinoma / Multifocal Breast Carcinoma / Progesterone Receptor Positive / Synchronous Bilateral Breast Carcinoma1
3Active Not RecruitingTreatmentMetastatic Breast Cancer3
3CompletedNot AvailableBreast Cancer / Fatigue / Sleep disorders and disturbances1
3CompletedPreventionBreast Cancer1
3CompletedTreatmentBreast Cancer6
3CompletedTreatmentLocally Advanced Breast Cancer (LABC) / Metastatic Breast Cancer1
3CompletedTreatmentMale Breast Cancer1
3CompletedTreatmentMetastatic Breast Cancer3
3CompletedTreatmentNeoplasms, Breast4
3CompletedTreatmentPost Menopausal Breast Cancer1
3CompletedTreatmentProgression-free Survival1
3Enrolling by InvitationTreatmentCYP2D6 Polymorphism1
3RecruitingTreatmentAdvanced Breast Cancer1
3RecruitingTreatmentBreast Cancer3
3RecruitingTreatmentBreast Cancer / Hormone Receptor Positive Tumor / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast / Locally Advanced Malignant Neoplasm / Metastatic Breast Cancer1
3RecruitingTreatmentEstrogen Receptor Positive Breast Cancer / HER-2 Positive Breast Cancer1
3RecruitingTreatmentMetastatic Breast Cancer1
3TerminatedTreatmentBreast Cancer2
3TerminatedTreatmentFirst Line Metastatic Breast Cancer1
3Unknown StatusTreatmentBreast Cancer5
4CompletedNot AvailableNeoplasms, Breast1
4CompletedOtherHER2/Neu-negative Carcinoma of Breast / Hormone Receptor Positive Malignant Neoplasm of Breast / Recurrent Breast Cancer1
4CompletedTreatmentBreast Cancer2
4CompletedTreatmentHormono-depending Adjuvant Breast Cancer1
4CompletedTreatmentNeoplasms, Breast1
4CompletedTreatmentOestrogen Receptor Positive Advanced Breast Cancer1
4RecruitingTreatmentEarly Breast Cancer1
4RecruitingTreatmentMetastatic Breast Cancer1
4RecruitingTreatmentNeoplasms, Breast1
4RecruitingTreatmentSexuality1
4TerminatedNot AvailableNeoplasms, Breast1
4WithdrawnTreatmentHER2/Neu Negative / Invasive Breast Carcinoma / One to five years postmenopausal / Stage 0 Breast Cancer / Stage IA Breast Cancer1
Not AvailableActive Not RecruitingNot AvailableBreast Cancer1
Not AvailableActive Not RecruitingOtherHormone Receptor Positive Malignant Neoplasm of Breast / Metastatic Breast Cancer1
Not AvailableActive Not RecruitingTreatmentMale Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer1
Not AvailableCompletedNot AvailableBMI >30 kg/m2 / Breast Cancer / Joint Pain1
Not AvailableCompletedNot AvailableBreast Cancer2
Not AvailableCompletedNot AvailableBreast Cancer / Joint Pain / Pain1
Not AvailableCompletedNot AvailableNeoplasms, Breast1
Not AvailableCompletedNot AvailablePost Menopausal Women With Early Breast Cancer1
Not AvailableCompletedPreventionBreast Cancer1
Not AvailableCompletedTreatmentBreast Cancer4
Not AvailableCompletedTreatmentEstrogen Receptor-Positive Breast Cancer / Progesterone Receptor Positive Tumor / Recurrent Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
Not AvailableCompletedTreatmentMale Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer1
Not AvailableEnrolling by InvitationNot AvailableBreast Cancer1
Not AvailableRecruitingNot AvailableHR+ HER2- Men, Pre/Postmenopausal Advanced Breast Cancer / HR+ HER2- Postmenopausal Advanced Breast Cancer1
Not AvailableRecruitingTreatmentCarcinoma, Breast1
Not AvailableTerminatedNot AvailableBreast Cancer1
Not AvailableTerminatedNot AvailableInvasive Early Breast Cancer1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
  • Pfizer Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
Dosage forms
FormRouteStrength
TabletOral
TabletOral25 mg
TabletOral25 mg/1
Tablet, film coatedOral25 mg/1
Tablet, sugar coatedOral25 mg/1
Prices
Unit descriptionCostUnit
Aromasin 25 mg tablet13.77USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4808616No1989-02-282011-04-01Us
CA2409059No2006-04-182021-04-25Canada
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)155.13 °CNot Available
water solubilityNon-solubleNot Available
logP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00683 mg/mLALOGPS
logP2.67ALOGPS
logP3.87ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.96ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.03 m3·mol-1ChemAxon
Polarizability33.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9778
Caco-2 permeable+0.7992
P-glycoprotein substrateSubstrate0.5589
P-glycoprotein inhibitor IInhibitor0.8974
P-glycoprotein inhibitor IINon-inhibitor0.6749
Renal organic cation transporterNon-inhibitor0.6499
CYP450 2C9 substrateNon-substrate0.8764
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7167
CYP450 1A2 substrateNon-inhibitor0.8552
CYP450 2C9 inhibitorNon-inhibitor0.9224
CYP450 2D6 inhibitorNon-inhibitor0.9373
CYP450 2C19 inhibitorNon-inhibitor0.751
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8276
Ames testNon AMES toxic0.9483
CarcinogenicityNon-carcinogens0.9245
BiodegradationNot ready biodegradable0.9539
Rat acute toxicity1.7582 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.76
hERG inhibition (predictor II)Non-inhibitor0.7791
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, 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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0190000000-5e04b3359ea2370bbde1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0950000000-0daf2c711395130c78a2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-006t-0910000000-58ddee06caa2cdb4eeac
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-006t-0910000000-64dd2bfc1eef30f5b766
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00wa-0900000000-ec533e47176e668d1ee9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0980000000-457e7fb9bd5073d9521a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0090000000-cc584f39a06f24401467
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-1960000000-22b6bd7c2ccea9c0c648
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00dj-2910000000-32edf95f8027c36c74ce
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fu-3900000000-84dacb108ccc2572ab41
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0596-5900000000-f4ef5b1c0c3093d9be81
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-054o-7900000000-d4fd55a1386141770feb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0090000000-d372ca664e7a339d245e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-1970000000-6aca0caa93beac3bf271
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-006w-2910000000-2f4bac4fb8744faeb793
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fu-3900000000-93e6d94ff92391e3ae17
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0596-4900000000-3888c20b2af766bfbd28
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-054o-7900000000-e5ae5c87edd46bea9bdf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0890000000-43dff5a59fc535cf2f01
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0790000000-46727c37da42caccba4f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-0910000000-1483760a934897cf3b7a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0009000000-0a3cc4550e16db4e3b05
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0090000000-8292cd5caa67529123d5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0290000000-3017fa06837d687a9ed9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-006t-0930000000-70c14a429cc679c17e57
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-1890000000-1fcf62ddeb8dd8441390

Taxonomy

Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-1,4-steroids / 17-oxosteroids / Delta-1,4-steroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / Oxosteroid / 17-oxosteroid / 3-oxosteroid / 3-oxo-delta-1,4-steroid / Delta-1,4-steroid / Cyclic ketone / Ketone / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
17-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid (CHEBI:4953)

Targets

Details
1. Cytochrome P450 19A1
Kind
Protein
Organism
Humans
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. Koutras A, Giannopoulou E, Kritikou I, Antonacopoulou A, Evans TR, Papavassiliou AG, Kalofonos H: Antiproliferative effect of exemestane in lung cancer cells. Mol Cancer. 2009 Nov 24;8:109. doi: 10.1186/1476-4598-8-109. [PubMed:19930708]
  3. Robinson A: A review of the use of exemestane in early breast cancer. Ther Clin Risk Manag. 2009 Feb;5(1):91-8. Epub 2009 Mar 26. [PubMed:19436613]
  4. Untch M, Jackisch C: Exemestane in early breast cancer: a review. Ther Clin Risk Manag. 2008 Dec;4(6):1295-304. [PubMed:19337436]
  5. Barnadas A, Gil M, Gonzalez S, Tusquets I, Munoz M, Arcusa A, Prieto L, Margeli-Vila M, Moreno A: Exemestane as primary treatment of oestrogen receptor-positive breast cancer in postmenopausal women: a phase II trial. Br J Cancer. 2009 Feb 10;100(3):442-9. doi: 10.1038/sj.bjc.6604868. Epub 2009 Jan 20. [PubMed:19156139]
  6. Abrial C, Durando X, Mouret-Reynier MA, Thivat E, Bayet-Robert M, Nayl B, Dubray P, Pomel C, Chollet P, Penault-Llorca F: Role of neo-adjuvant hormonal therapy in the treatment of breast cancer: a review of clinical trials. Int J Gen Med. 2009 Jul 30;2:129-40. [PubMed:20360896]
  7. Nabholtz JM: Long-term safety of aromatase inhibitors in the treatment of breast cancer. Ther Clin Risk Manag. 2008 Feb;4(1):189-204. [PubMed:18728707]
  8. Brueggemeier RW: Update on the use of aromatase inhibitors in breast cancer. Expert Opin Pharmacother. 2006 Oct;7(14):1919-30. [PubMed:17020418]
  9. Brueggemeier RW, Hackett JC, Diaz-Cruz ES: Aromatase inhibitors in the treatment of breast cancer. Endocr Rev. 2005 May;26(3):331-45. Epub 2005 Apr 6. [PubMed:15814851]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Robinson A: A review of the use of exemestane in early breast cancer. Ther Clin Risk Manag. 2009 Feb;5(1):91-8. Epub 2009 Mar 26. [PubMed:19436613]
  2. Kamdem LK, Flockhart DA, Desta Z: In vitro cytochrome P450-mediated metabolism of exemestane. Drug Metab Dispos. 2011 Jan;39(1):98-105. doi: 10.1124/dmd.110.032276. Epub 2010 Sep 28. [PubMed:20876785]
  3. Peterson A, Xia Z, Chen G, Lazarus P: In vitro metabolism of exemestane by hepatic cytochrome P450s: impact of nonsynonymous polymorphisms on formation of the active metabolite 17beta-dihydroexemestane. Pharmacol Res Perspect. 2017 Apr 27;5(3):e00314. doi: 10.1002/prp2.314. eCollection 2017 Jun. [PubMed:28603633]
Kind
Protein
Organism
Humans
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. di Salle E, Ornati G, Giudici D, Lassus M, Evans TR, Coombes RC: Exemestane (FCE 24304), a new steroidal aromatase inhibitor. J Steroid Biochem Mol Biol. 1992 Sep;43(1-3):137-43. [PubMed:1525055]
  2. Gene card, CYP19A1 [Link]
  3. FDA label, Exemestane [Link]

Drug created on June 13, 2005 07:24 / Updated on December 07, 2019 14:27