Identification

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 acts as a false substrate for the aromatase enzyme, and is processed to an intermediate that binds irreversibly to the active site of the enzyme causing its inactivation.

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 ExemestaneTablet25 mgOralActavis Pharma Company2012-07-26Not applicableCanada
AromasinTablet25 mg/1OralPhysicians Total Care, Inc.2005-06-29Not applicableUs
AromasinTablet25 mg/1OralPharmacia & Upjohn Inc1999-10-21Not applicableUs00009 7663 04 nlmimage10 fd12fea7
AromasinTablet25 mgOralPfizer2000-08-17Not applicableCanada
ExemestaneTablet, sugar coated25 mg/1OralGreenstone, Llc2011-04-01Not applicableUs59762 2858 01 nlmimage10 00200070
Gd-exemestaneTablet25 mgOralGenmed A Division Of Pfizer Canada IncNot applicableNot applicableCanada
Med-exemestaneTablet25 mgOralGeneric Medical Partners Inc2013-12-02Not applicableCanada
Mylan-exemestaneTablet25 mgOralMylan PharmaceuticalsNot applicableNot applicableCanada
Teva-exemestaneTablet25 mgOralTeva2013-10-01Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-exemestaneTablet25 mgOralApotex Corporation2014-05-01Not applicableCanada
ExemestaneTablet25 mg/1OralAmerincan Health Packaging2015-03-312017-04-30Us
ExemestaneTablet, film coated25 mg/1OralWest Ward Pharmaceutical2011-04-01Not applicableUs
ExemestaneTablet, film coated25 mg/1OralMylan Pharmaceuticals2017-03-10Not applicableUs
ExemestaneTablet25 mg/1OralAlvogen, Inc.2014-07-25Not applicableUs47781 0108 30 nlmimage10 ee3df73f
ExemestaneTablet25 mg/1OralUpsher Smith Laboratories2017-07-27Not applicableUs
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][[email protected]@]12CCC(=O)[[email protected]@]1(C)CC[[email protected]@]1([H])[[email protected]@]2([H])CC(=C)C2=CC(=O)C=C[[email protected]]12C

Pharmacology

Indication

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

Structured Indications
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 acts as a false substrate for the aromatase enzyme, and is processed to an intermediate that binds irreversibly to the active site of the enzyme causing its inactivation, an effect also known as "suicide inhibition". 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
Human
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
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Exemestane.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Exemestane.Experimental
AmiodaroneThe metabolism of Exemestane can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Exemestane can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Exemestane.Approved, Investigational
AtazanavirThe metabolism of Exemestane can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Exemestane can be decreased when combined with Atomoxetine.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Exemestane.Approved, Investigational
BoceprevirThe metabolism of Exemestane can be decreased when combined with Boceprevir.Withdrawn
BortezomibThe metabolism of Exemestane can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Exemestane can be decreased when it is combined with Bosentan.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Exemestane.Approved
CarbamazepineThe serum concentration of Exemestane can be decreased when it is combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Exemestane can be increased when it is combined with Ceritinib.Approved
ChlorotrianiseneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Chlorotrianisene.Withdrawn
ClarithromycinThe metabolism of Exemestane can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Exemestane can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Exemestane can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Exemestane can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Exemestane can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated estrogensThe therapeutic efficacy of Exemestane can be decreased when used in combination with Conjugated estrogens.Approved
CrizotinibThe metabolism of Exemestane can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Exemestane.Approved, Investigational
CyclosporineThe metabolism of Exemestane can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Exemestane.Experimental
DabrafenibThe serum concentration of Exemestane can be decreased when it is combined with Dabrafenib.Approved
DaidzeinThe therapeutic efficacy of Exemestane can be decreased when used in combination with Daidzein.Experimental
DarunavirThe metabolism of Exemestane can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Exemestane can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Exemestane can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Exemestane can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Exemestane.Approved
DienestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Dienestrol.Approved
DiethylstilbestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Diethylstilbestrol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Exemestane.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Exemestane.Approved
DihydroergotamineThe metabolism of Exemestane can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Exemestane can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Exemestane.Approved, Investigational
DoxycyclineThe metabolism of Exemestane can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Exemestane can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Exemestane can be decreased when it is combined with Enzalutamide.Approved
EpimestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Epimestrol.Experimental
EquolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Equol.Investigational
ErythromycinThe metabolism of Exemestane can be decreased when combined with Erythromycin.Approved, Vet Approved
EstradiolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Estradiol.Approved, Investigational, Vet Approved
EstriolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Estriol.Approved, Vet Approved
EstroneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Estrone.Approved
Ethinyl EstradiolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Ethinyl Estradiol.Approved
FluconazoleThe metabolism of Exemestane can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Exemestane can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Exemestane can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Exemestane can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Exemestane can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Exemestane can be increased when it is combined with Fusidic Acid.Approved
GenisteinThe therapeutic efficacy of Exemestane can be decreased when used in combination with Genistein.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Exemestane.Experimental
HexestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Hexestrol.Withdrawn
IdelalisibThe serum concentration of Exemestane can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Exemestane can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Exemestane can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Exemestane can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Exemestane can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Exemestane can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Exemestane can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Exemestane can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Exemestane.Experimental
LopinavirThe metabolism of Exemestane can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Exemestane can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Exemestane can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Exemestane can be decreased when it is combined with Lumacaftor.Approved
MestranolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Mestranol.Approved
MethadoneThe serum concentration of Methadone can be increased when it is combined with Exemestane.Approved
MethallenestrilThe therapeutic efficacy of Exemestane can be decreased when used in combination with Methallenestril.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Exemestane.Experimental
MifepristoneThe serum concentration of Exemestane can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Exemestane can be decreased when it is combined with Mitotane.Approved
MoxestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Moxestrol.Experimental
NefazodoneThe metabolism of Exemestane can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Exemestane can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Exemestane can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Exemestane can be decreased when it is combined with Nevirapine.Approved
NilotinibThe metabolism of Exemestane can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Exemestane can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Exemestane.Experimental
OsimertinibThe serum concentration of Exemestane can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Exemestane.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Exemestane.Approved, Vet Approved
PalbociclibThe serum concentration of Exemestane can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe serum concentration of Exemestane can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Exemestane.Experimental
PhenobarbitalThe serum concentration of Exemestane can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Exemestane can be decreased when it is combined with Phenytoin.Approved, Vet Approved
Polyestradiol phosphateThe therapeutic efficacy of Exemestane can be decreased when used in combination with Polyestradiol phosphate.Approved
PosaconazoleThe metabolism of Exemestane can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe serum concentration of Exemestane can be decreased when it is combined with Primidone.Approved, Vet Approved
PromestrieneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Promestriene.Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Exemestane.Experimental
QuinestrolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Quinestrol.Approved
RanolazineThe metabolism of Exemestane can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe serum concentration of Exemestane can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Exemestane can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Exemestane can be decreased when it is combined with Rifapentine.Approved
RitonavirThe metabolism of Exemestane can be decreased when combined with Ritonavir.Approved, Investigational
SaquinavirThe metabolism of Exemestane can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Exemestane.Approved
SecoisolariciresinolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Secoisolariciresinol.Investigational
SildenafilThe metabolism of Exemestane can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Exemestane can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Exemestane can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Exemestane can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Exemestane can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Exemestane can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
Synthetic Conjugated Estrogens, AThe therapeutic efficacy of Exemestane can be decreased when used in combination with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe therapeutic efficacy of Exemestane can be decreased when used in combination with Synthetic Conjugated Estrogens, B.Approved
TelaprevirThe metabolism of Exemestane can be decreased when combined with Telaprevir.Withdrawn
TelithromycinThe metabolism of Exemestane can be decreased when combined with Telithromycin.Approved
TiboloneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Tibolone.Approved
TiclopidineThe metabolism of Exemestane can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Exemestane can be decreased when it is combined with Tocilizumab.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Exemestane.Approved, Investigational
VenlafaxineThe metabolism of Exemestane can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Exemestane can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Exemestane can be decreased when combined with Voriconazole.Approved, Investigational
ZeranolThe therapeutic efficacy of Exemestane can be decreased when used in combination with Zeranol.Vet Approved
ZiprasidoneThe metabolism of Exemestane can be decreased when combined with Ziprasidone.Approved
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
HMDB15125
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 RecruitingTreatmentCancer, Breast2
1Active Not RecruitingTreatmentMetastatic or Locally-advanced Unresectable Breast Cancer1
1Active Not RecruitingTreatmentNeoplasms1
1Active Not RecruitingTreatmentNeoplasms / Neoplasms, Breast / Neoplasms, Kidney / Pancreatic Neuroendocine Neoplasms1
1Active Not RecruitingTreatmentStage IV Non-Small Cell Lung Cancer1
1CompletedTreatmentCancer, Breast1
1CompletedTreatmentCancer, Breast / Estrogen Receptor Breast Cancer / Lung Cancer Non-Small Cell Cancer (NSCLC) / Lung Cancers1
1CompletedTreatmentMalignant Lymphomas / Tumors, Solid1
1CompletedTreatmentNeoplasms1
1RecruitingTreatmentAdvanced Breast Cancer1
1RecruitingTreatmentCancer, Breast3
1RecruitingTreatmentCancer, Breast / Carcinoma, Breast / Malignant Neoplasm of Breast1
1RecruitingTreatmentCancer, Breast / Estrogen Receptor Positive Breast Cancer1
1RecruitingTreatmentNeoplasms, Breast1
1SuspendedBasic ScienceHealthy Volunteers1
1TerminatedTreatmentEstrogen Receptor Positive / HER2/Neu Negative / Male Breast Carcinoma / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
1WithdrawnTreatmentMetastatic Breast Cancer (MBC)1
1, 2CompletedTreatmentER+ Breast Cancer / FGFR Inhibition, Pharmacokinetics, Biomarkers1
1, 2Not Yet RecruitingTreatmentPremenopausal Breast Cancer1
1, 2RecruitingTreatmentAdvanced Estrogen Receptor Positive HER2- Breast Cancer1
1, 2RecruitingTreatmentCancer, Breast1
1, 2RecruitingTreatmentHormone Receptor (HR)-Positive Breast Cancer / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast1
1, 2RecruitingTreatmentNeoplasms, Breast1
1, 2TerminatedTreatmentCancer, Breast1
1, 2TerminatedTreatmentMetastatic Breast Cancer (MBC)1
1, 2TerminatedTreatmentNeoplasms, Breast1
1, 2Unknown StatusTreatmentCancer, Breast1
2Active Not RecruitingTreatmentCancer, Breast7
2Active Not RecruitingTreatmentCancer, Breast / Stage II Breast Cancer / Stage III Breast Cancer1
2Active Not RecruitingTreatmentEstrogen-receptor Positive Invasive Metastatic Breast Cancer1
2Active Not RecruitingTreatmentHormone Receptor Positive Breast Cancer1
2Active Not RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2Active Not RecruitingTreatmentMetastatic ER+ Her2- Breast Cancer / One to five years postmenopausal1
2Active Not RecruitingTreatmentNeoplasms, Breast1
2CompletedPreventionAdvanced Breast Cancer1
2CompletedPreventionNeoplasms, Breast1
2CompletedTreatmentBreast Cancer, Estrogen Receptor-Positive / Cancer, Breast / ER+ Breast Cancer / Estrogen Receptor-Positive Breast Cancer1
2CompletedTreatmentCancer, Breast9
2CompletedTreatmentCancer, Ovarian1
2CompletedTreatmentEndometrial Cancers1
2CompletedTreatmentHer2 Negative Breast Cancer Patients1
2CompletedTreatmentMetastatic Beast Cancer1
2CompletedTreatmentMetastatic Breast Cancer (MBC)2
2CompletedTreatmentNeoplasms, Breast3
2CompletedTreatmentProstate Cancer1
2Not Yet RecruitingTreatmentAtypical Hyperplasia / Endometrial Intraepithelial Neoplasia / Grade 1 Endometrial Endometrioid Adenocarcinoma / One to five years postmenopausal1
2Not Yet RecruitingTreatmentBreast Cancer Metastatic1
2Not Yet RecruitingTreatmentMetastatic Breast Cancer (MBC)1
2Not Yet RecruitingTreatmentNeoplasms, Breast1
2RecruitingPreventionEstrogen 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 I Breast Carcinoma / 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
2RecruitingTreatmentAdvanced Breast Cancer1
2RecruitingTreatmentAdvanced or Recurrent Breast Cancer1
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
2RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2RecruitingTreatmentMetastatic Breast Cancer (MBC)2
2RecruitingTreatmentNeoplasms, Breast3
2RecruitingTreatmentPrimary Breast Cancer AR+ve TNBN / Primary Breast Cancer ER+ve1
2TerminatedTreatmentAdvanced Breast Cancer1
2TerminatedTreatmentCancer, Breast2
2TerminatedTreatmentEstrogen Receptor-Positive Breast Cancer / HER2-Negative Breast Cancer / Progesterone Receptor-positive Breast Cancer / Stage I Breast Carcinoma / Stage II Breast Cancer / Stage IIIA Breast Cancer1
2TerminatedTreatmentHormone-receptors Positive Breast Cancer1
2TerminatedTreatmentNeoplasms, Breast2
2Unknown StatusPreventionNeoplasms, Breast1
2Unknown StatusTreatmentCancer, Breast1
2Unknown StatusTreatmentHormone Receptor Positive Malignant Neoplasm of Breast1
2WithdrawnTreatmentCancer, Breast3
2WithdrawnTreatmentMetastatic Breast Cancer (MBC)1
2WithdrawnTreatmentNeoplasms, Breast1
2WithdrawnTreatmentStage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer1
2, 3TerminatedTreatmentCancer, Breast1
2, 3Unknown StatusTreatmentCancer, Breast1
3Active Not RecruitingPreventionCancer, Breast1
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 RecruitingTreatmentCancer, Breast3
3Active Not RecruitingTreatmentCancer, Breast / 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
3CompletedNot AvailableCancer, Breast / Sleep disorders and disturbances / Tiredness1
3CompletedTreatmentCancer, Breast5
3CompletedTreatmentLocally Advanced Breast Cancer (LABC) / Metastatic Breast Cancer (MBC)1
3CompletedTreatmentMetastatic Breast Cancer (MBC)3
3CompletedTreatmentNeoplasms, Breast4
3CompletedTreatmentProgression-free Survival1
3Not Yet RecruitingTreatmentCancer, Breast1
3RecruitingTreatmentBreast Cancer Metastatic1
3RecruitingTreatmentCancer, Breast3
3RecruitingTreatmentCancer, Breast / Hormone Receptor Positive Tumor / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast / Locally Advanced Malignant Neoplasm / Metastatic Breast Cancer (MBC)1
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 / HER2/Neu Negative / Male Breast Carcinoma / Progesterone Receptor Positive / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
3RecruitingTreatmentMale Breast Cancer1
3RecruitingTreatmentMetastatic Breast Cancer (MBC)2
3TerminatedTreatmentCancer, Breast2
3TerminatedTreatmentFirst Line Metastatic Breast Cancer1
3Unknown StatusTreatmentCancer, Breast5
4Active Not RecruitingTreatmentHormono-depending Adjuvant Breast Cancer1
4CompletedOtherBreast Cancer Recurrent / HER2/Neu-negative Carcinoma of Breast / Hormone Receptor Positive Malignant Neoplasm of Breast1
4CompletedTreatmentCancer, Breast1
4CompletedTreatmentNeoplasms, Breast1
4CompletedTreatmentOestrogen Receptor Positive Advanced Breast Cancer1
4Not Yet RecruitingTreatmentHER2/Neu Negative / Invasive Breast Carcinoma / One to five years postmenopausal / Stage 0 Breast Cancer / Stage IA Breast Cancer1
4RecruitingNot AvailableNeoplasms, Breast1
4RecruitingTreatmentCYP2D6 Polymorphism1
4RecruitingTreatmentSexuality1
4TerminatedNot AvailableNeoplasms, Breast1
4Unknown StatusTreatmentCancer, Breast1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast1
Not AvailableActive Not RecruitingTreatmentMale Breast Cancer / Recurrent Breast Cancer / Stage IV Breast Cancer2
Not AvailableCompletedNot AvailableArthralgia / BMI >30 kg/m2 / Cancer, Breast1
Not AvailableCompletedNot AvailableArthralgia / Cancer, Breast / Pain1
Not AvailableCompletedNot AvailableCancer, Breast2
Not AvailableCompletedNot AvailableNeoplasms, Breast1
Not AvailableCompletedNot AvailablePost Menopausal Women With Early Breast Cancer1
Not AvailableCompletedPreventionCancer, Breast1
Not AvailableCompletedTreatmentCancer, Breast3
Not AvailableCompletedTreatmentEstrogen Receptor-Positive Breast Cancer / Progesterone Receptor Positive Tumor / Recurrent Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
Not AvailableEnrolling by InvitationNot AvailableCancer, Breast1
Not AvailableRecruitingTreatmentCarcinoma, Breast1
Not AvailableTerminatedNot AvailableCancer, Breast1
Not AvailableTerminatedNot AvailableInvasive Early Breast Cancer1

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
TabletOral25 mg/1
TabletOral25 mg
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)
US4808616No1994-04-012011-04-01Us
CA2409059No2006-04-182021-04-25Canada

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
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. 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
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
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. 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
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]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2017 21:49