Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H24O2 |
Molecular Weight | 296.4034 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC(=C)C4=CC(=O)C=C[C@]34C
InChI
InChIKey=BFYIZQONLCFLEV-DAELLWKTSA-N
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
Molecular Formula | C20H24O2 |
Molecular Weight | 296.4034 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00990Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020753s009s011s012lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00990
Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020753s009s011s012lbl.pdf
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. 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. Exemestane is marketed under the trade name Aromasin.
Originator
Sources: http://adisinsight.springer.com/drugs/800000826
Curator's Comment: # Pfizer
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22951074 |
50.1 nM [IC50] | ||
Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25738757 |
28.02 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Aromasin Approved UseAROMASIN is an aromatase inhibitor indicated for:
adjuvant treatment of postmenopausal women with estrogen-receptor positive early breast cancer who have received two to three years of tamoxifen and are switched to AROMASIN for completion of a total of five consecutive years of adjuvant hormonal therapy.
the treatment of advanced breast cancer in postmenopausal women whose disease has progressed following tamoxifen therapy Launch Date1999 |
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Primary | Aromasin Approved UseAROMASIN is an aromatase inhibitor indicated for:
adjuvant treatment of postmenopausal women with estrogen-receptor positive early breast cancer who have received two to three years of tamoxifen and are switched to AROMASIN for completion of a total of five consecutive years of adjuvant hormonal therapy.
the treatment of advanced breast cancer in postmenopausal women whose disease has progressed following tamoxifen therapy Launch Date1999 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.1 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/14671195 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
EXEMESTANE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
36.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/14671195 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
EXEMESTANE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/14671195 |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
EXEMESTANE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: Page: p.678 |
unhealthy, 37-77 n = 4 Health Status: unhealthy Condition: Breast cancer Age Group: 37-77 Sex: F Population Size: 4 Sources: Page: p.678 |
|
800 mg single, oral Highest studied dose Dose: 800 mg Route: oral Route: single Dose: 800 mg Sources: Page: p.5935 |
healthy, 48 - 75 n = 3 Health Status: healthy Age Group: 48 - 75 Sex: F Population Size: 3 Sources: Page: p.5935 |
|
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.4 |
unhealthy n = 2252 Health Status: unhealthy Condition: Breast cancer Sex: F Population Size: 2252 Sources: Page: p.4 |
Disc. AE: Myocardial infarction, Angina... AEs leading to discontinuation/dose reduction: Myocardial infarction Sources: Page: p.4Angina Myocardial ischemia Cardiac failure (0.4%) |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Breast cancer Sex: F Sources: Page: p.1 |
Disc. AE: Bone density increased, Fetal damage... AEs leading to discontinuation/dose reduction: Bone density increased Sources: Page: p.1Fetal damage |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cardiac failure | 0.4% Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.4 |
unhealthy n = 2252 Health Status: unhealthy Condition: Breast cancer Sex: F Population Size: 2252 Sources: Page: p.4 |
Angina | Disc. AE | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.4 |
unhealthy n = 2252 Health Status: unhealthy Condition: Breast cancer Sex: F Population Size: 2252 Sources: Page: p.4 |
Myocardial infarction | Disc. AE | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.4 |
unhealthy n = 2252 Health Status: unhealthy Condition: Breast cancer Sex: F Population Size: 2252 Sources: Page: p.4 |
Myocardial ischemia | Disc. AE | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.4 |
unhealthy n = 2252 Health Status: unhealthy Condition: Breast cancer Sex: F Population Size: 2252 Sources: Page: p.4 |
Bone density increased | Disc. AE | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Breast cancer Sex: F Sources: Page: p.1 |
Fetal damage | Disc. AE | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Breast cancer Sex: F Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
Current role of endocrine therapy in the management of breast cancer. | 2002 |
|
Evolving uses of hormonal agents for breast cancer therapy. | 2002 |
|
The impact of hormonal treatments on quality of life of patients with metastatic breast cancer. | 2002 |
|
Aromatase inhibitors in breast cancer therapy. | 2002 Apr |
|
The role of aromatase inactivators in the treatment of breast cancer. | 2002 Aug |
|
[Early phase II dose-finding study of exemestane in postmenopausal patients with advanced/recurrent breast cancer]. | 2002 Jul |
|
[Phase I multiple-dose administration study of exemestane in postmenopausal women]. | 2002 Jul |
|
[Phase I single-dose administration study of exemestane in postmenopausal women]. | 2002 Jul |
|
Exemestane: a potent irreversible aromatase inactivator and a promising advance in breast cancer treatment. | 2002 Jun |
|
Neoadjuvant endocrine therapy of breast cancer: a surgical perspective. | 2002 Nov |
|
An overview of the pharmacology and pharmacokinetics of the newer generation aromatase inhibitors anastrozole, letrozole, and exemestane. | 2002 Nov 1 |
|
Exemestane: treatment of breast cancer with selective inactivation of aromatase. | 2002 Nov 15 |
|
The evolving role of aromatase inhibitors in breast cancer. | 2002 Oct |
|
Sequencing of endocrine therapies in breast cancer--integration of recent data. | 2002 Oct |
|
New generation aromatase inhibitors--from the advanced to the adjuvant setting. | 2002 Oct |
|
Sequential hormonal therapy for metastatic breast cancer after adjuvant tamoxifen or anastrozole. | 2003 |
|
[Perspectives for the hormonal therapy of breast cancer]. | 2003 |
|
Advances in endocrine treatments for postmenopausal women with metastatic and early breast cancer. | 2003 |
|
8th international conference: primary therapy of early breast cancer, St Gallen, Switzerland, March 12-15 2003. | 2003 |
|
Aromatase inhibitors for treatment of postmenopausal patients with breast cancer. | 2003 Apr |
|
Update on the current use of hormonals as therapy in advanced breast cancer. | 2003 Apr |
|
The role of aromatase inhibitors in early breast cancer. | 2003 Apr |
|
Aromatase inhibitors in early breast cancer treatment. | 2003 Aug |
|
The role of aromatase inhibitors in the treatment of metastatic breast cancer. | 2003 Aug |
|
Pharmacokinetics of third-generation aromatase inhibitors. | 2003 Aug |
|
Aromatase inhibitors: mechanism of action and role in the treatment of breast cancer. | 2003 Aug |
|
Should aromatase inhibitors replace tamoxifen? | 2003 Aug |
|
Emerging role of aromatase inhibitors in the adjuvant setting. | 2003 Aug |
|
Applicability of the intratumor aromatase preclinical model to predict clinical trial results with endocrine therapy. | 2003 Aug |
|
A comparison of the efficacy of aromatase inhibitors in second-line treatment of metastatic breast cancer. | 2003 Aug |
|
The current status of aromatase inhibitors in the management of breast cancer. | 2003 Aug |
|
[Treatment of advanced metastatic breast cancer with exemestane, a multicenter randomized controlled study of 195 cases]. | 2003 Feb 10 |
|
Clinical differences among the aromatase inhibitors. | 2003 Jan |
|
Pharmacology and pharmacokinetics of the newer generation aromatase inhibitors. | 2003 Jan |
|
Is there a benefit by the sequence anastrozole-formestane for postmenopausal metastatic breast cancer women? | 2003 Jul |
|
Bone turnover markers and insulin-like growth factor components in metastatic breast cancer: results from a randomised trial of exemestane vs megestrol acetate. | 2003 Jul-Aug |
|
Long-term toxicities of selective estrogen-receptor modulators and antiaromatase agents. | 2003 May |
|
Could exemestane affect insulin-like growth factors, interleukin 6 and bone metabolism in postmenopausal advanced breast cancer patients after failure on aminoglutethimide, anastrozole or letrozole? | 2003 May |
|
A roundtable discussion of aromatase inhibitors as therapy for breast cancer. | 2003 May-Jun |
|
Economic evaluation of antiaromatase agents in the second-line treatment of metastatic breast cancer. | 2003 Nov |
|
[Pharmacological and clinical profile of exemestane (Aromasin), a novel irreversible aromatase inhibitor]. | 2003 Oct |
|
Celecoxib anti-aromatase neoadjuvant (CAAN) trial for locally advanced breast cancer: preliminary report. | 2003 Sep |
|
An integrated view of aromatase and its inhibition. | 2003 Sep |
|
Aromatase inhibitors versus tamoxifen for management of postmenopausal breast cancer in the advanced disease and neoadjuvant settings. | 2003 Sep |
|
Aromatase inhibitors as adjuvant therapies in patients with breast cancer. | 2003 Sep |
|
Neoadjuvant comparisons of aromatase inhibitors and tamoxifen: pretreatment determinants of response and on-treatment effect. | 2003 Sep |
|
The intratumoral aromatase model: studies with aromatase inhibitors and antiestrogens. | 2003 Sep |
|
[Clinical trial on exemestane in the treatment of postmenopausal women with advanced breast cancer]. | 2003 Sep |
|
Exemestane seems to stimulate tumour growth in men with prostate carcinoma. | 2003 Sep |
|
Mature results of a randomized phase II multicenter study of exemestane versus tamoxifen as first-line hormone therapy for postmenopausal women with metastatic breast cancer. | 2003 Sep |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25738757
Exemestane (28 uM) inhibits the growth of MCF‑7 cells.
Substance Class |
Chemical
Created
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Record UNII |
NY22HMQ4BX
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Record Status |
Validated (UNII)
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LIVERTOX |
NBK548926
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NDF-RT |
N0000175080
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WHO-VATC |
QL02BG06
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FDA ORPHAN DRUG |
60191
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WHO-ATC |
L02BG06
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NDF-RT |
N0000175563
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NCI_THESAURUS |
C2017
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DTXSID5023037
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60198
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CHEMBL1200374
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6770
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EXEMESTANE
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7463
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7073
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DB00990
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m5224
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NY22HMQ4BX
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4953
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258494
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LL-46
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C1097
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107868-30-4
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SUB07492MIG
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Exemestane
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100000092298
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NY22HMQ4BX
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1269050
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758907
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C056516
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1122
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE | |||
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DERIVATIVE -> PARENT |
PLASMA; URINE
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EXCRETED UNCHANGED |
URINE
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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BINDER->LIGAND |
BINDING
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DERIVATIVE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
PLASMA; URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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