exemestane

AROMASIN

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/08 21:02:27」(JST)

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Exemestane

Systematic (IUPAC) name
6-Methylideneandrosta-1,4-diene-3,17-dione
Clinical data
Trade names	Aromasin
AHFS/Drugs.com	monograph
MedlinePlus	a607006
Pregnancy cat.	D
Legal status	Rx only
Routes	Oral
Pharmacokinetic data
Bioavailability	~60%
Protein binding	90%
Half-life	27 hours
Identifiers
CAS number	107868-30-4 Y
ATC code	L02BG06
PubChem	CID 60198
DrugBank	DB00990
ChemSpider	54278 Y
UNII	NY22HMQ4BX Y
KEGG	D00963 Y
ChEMBL	CHEMBL1200374 Y
Chemical data
Formula	C20H24O2
Mol. mass	296.403 g/mol
SMILES O=C\1\C=C/[C@]3(C(=C/1)/C(=C)C[C@H]4[C@@H]2CCC(=O)[C@]2(CC[C@H]34)C)C
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 Y Key:BFYIZQONLCFLEV-DAELLWKTSA-N Y
Y (what is this?)  (verify)

Exemestane (trade name Aromasin) is a drug used to treat breast cancer. It is a member of the class of drugs known as aromatase inhibitors. Some breast cancers require estrogen to grow. Those cancers have estrogen receptors (ERs), and are called ER-positive. They may also be called estrogen-responsive, hormonally-responsive, or hormone-receptor-positive. Aromatase is an enzyme that synthesizes estrogen. Aromatase inhibitors block the synthesis of estrogen. This lowers the estrogen level, and slows the growth of cancers.

Function

Exemestane is an oral steroidal aromatase inhibitor that is used in ER-positive breast cancer in addition to surgery and/or radiation in post-menopausal women.

The main source of estrogen is the ovaries in premenopausal women, while in post-menopausal women most of the body's estrogen is produced via the conversion of androgens into estrogen by the aromatase enzyme in the peripheral tissues (i.e. adipose tissue like that of the breast) and a number of sites in the brain. Estrogen is produced locally via the actions of the aromatase enzyme in these peripheral tissues where it acts locally. Any circulating estrogen in post-menopausal women as well as men is the result of estrogen escaping local metabolism and entering the circulatory system.

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." By being structurally similar to enzyme targets, Exemestane permanently binds to the enzymes, preventing them from converting androgen into estrogen.

The estrogen suppression rate for exemestane varies from 85% for estradiol (E2) to 95% for estrone (E1).^{[citation needed]}

Clinical uses

Exemestane is indicated for the 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 it for completion of a total of five consecutive years of adjuvant hormonal therapy. US FDA approval was in October 2005.

Exemestane is indicated for the treatment of advanced breast cancer in postmenopausal women whose disease has progressed following tamoxifen therapy.

A Phase III trial has been reported which concluded that the use of exemestane in postmenopausal women at an increased risk for breast cancer reduced the incidence of invasive breast cancer. In 4,560 women, after 35 months, the administration of exemestane at a dose of 25 mg/day resulted in a 65% reduction in the risk of breast cancer compared with placebo; annual incidence rates were 0.19% and 0.55%, respectively (hazard ratio: 0.35; 95% CI [0.18-0.70]; p = 0.002).

Therapeutic Efficacy

Oral exemestane 25 mg/day for 2–3 years of adjuvant therapy was generally more effective than 5 years of continuous adjuvant tamoxifen in the treatment of postmenopausal women with early-stage estrogen receptor-positive/unknown receptor status breast in a large well-designed trial. Preliminary data from the open-label TEAM trial comparing exemestane with tamoxifen indicates that exemestane 25 mg/day is also effective in the primary adjuvant treatment of early-stage breast cancer in postmenopausal women.

Interim phase III trial results in 2011 show that adding Afinitor (everolimus) to exemestane therapy against advanced breast cancer can significantly improve progression-free survival compared with exemestane therapy alone.

References

External links

• Aromasin official website
• Aromasin prescribing information

UpToDate Contents

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• 1. 転移性ホルモン受容体陽性乳癌に対する治療アプローチ：内分泌療法 treatment approach to metastatic hormone receptor positive breast cancer endocrine therapy
• 2. 非転移性ホルモン受容体陽性乳癌に対する補助内分泌療法 adjuvant endocrine therapy for non metastatic hormone receptor positive breast cancer
• 3. 乳癌予防のための選択的エストロゲン受容体調節因子およびアロマターゼ阻害剤 selective estrogen receptor modulators and aromatase inhibitors for breast cancer prevention
• 4. アロマターゼ阻害剤による骨量減少の評価およびマネージメント evaluation and management of aromatase inhibitor induced bone loss
• 5. 乳癌に対する術前補助化学療法：理論的根拠、治療前評価、および治療法の選択肢 neoadjuvant therapy for breast cancer rationale pretreatment evaluation and therapeutic options

English Journal

• Chemoprevention for Breast Cancer.

• Pruthi S1, Heisey RE, Bevers TB.
• Annals of surgical oncology.Ann Surg Oncol.2015 Oct;22(10):3230-5. doi: 10.1245/s10434-015-4715-9. Epub 2015 Jul 23.
• BACKGROUND: Many women at increased risk for breast cancer could benefit from preventive therapy. Preventive therapy options for breast cancer risk reduction have expanded in the last few years to include both selective receptor modulators (tamoxifen and raloxifene) and aromatase inhibitors (anastro
• PMID 26202562

• Economic Evaluations of Everolimus Versus Other Hormonal Therapies in the Treatment of HR(+)/HER2(-) Advanced Breast Cancer From a US Payer Perspective.

• Xie J1, Hao Y2, Zhou ZY3, Qi CZ3, De G4, Glück S5.
• Clinical breast cancer.Clin Breast Cancer.2015 Oct;15(5):e263-76. doi: 10.1016/j.clbc.2015.04.001. Epub 2015 Apr 23.
• INTRODUCTION: The objective of the study was to assess the cost-effectiveness of EVE+EXE versus endocrine monotherapies in the treatment of postmenopausal women with HR(+), HER2(-) ABC after failure of treatment with nonsteroidal aromatase inhibitors from a US third-party payer perspective.MATERIALS
• PMID 26048087

• Prognostic and predictive value of ERβ1 and ERβ2 in the Intergroup Exemestane Study (IES)-first results from PathIES†.

• Speirs V1, Viale G2, Mousa K3, Palmieri C4, Reed SN3, Nicholas H3, Cheang M5, Jassem J6, Lønning PE7, Kalaitzaki E5, van de Velde CJ8, Rasmussen BB9, Verhoeven DM10, Shaaban AM11, Bartlett JM12, Bliss JM5, Coombes RC13; PathIES Sub-Committee.
• Annals of oncology : official journal of the European Society for Medical Oncology / ESMO.Ann Oncol.2015 Sep;26(9):1890-7. doi: 10.1093/annonc/mdv242. Epub 2015 May 22.
• BACKGROUND: Intergroup Exemestane Study (IES) was a randomised study that showed a survival benefit of switching adjuvant endocrine therapy after 2-3 years from tamoxifen to exemestane. PathIES aimed to assess the potential prognostic and predictive value of ERβ1 and ERβ2 expression in primary tum
• PMID 26002610

Japanese Journal

• 症例報告 エベロリムスとエキセメスタンが奏効した濃厚な前治療歴を有する転移性乳癌の1例

• 西口 春香,尾浦 正二,吉増 達也 [他]
• 和歌山医学 66(1), 7-9, 2015-03
• NAID 40020434186

• Exemestane（EXE）術前６か月間投与により病理学的完全奏功（pCR）を得たER 陽性乳癌の１例

• 戸塚 勝理,黒住 献,松本 広志,坪井 美樹,久保 和之,林 祐二,二宮 淳,武井 寛幸,大久保 文恵,永井 成勲,井上 賢一,大庭 華子,黒住 昌史,堀口 淳,竹吉 泉
• The Kitakanto medical journal = 北関東医学 64(2), 228-228, 2014-05-01
• NAID 120005429892

• 術後7年目に癌性腹膜炎に続いて両側視神経転移を伴う髄膜播種を来した乳癌の1例

• 久保 秀文,中須賀 千代,多田 耕輔,宮原 誠,長谷川 博康,原田 有彦
• 山口医学 63(1), 25-30, 2014-02-01
• … She received 6 cycles of paclitaxel every week, after which an aromatase inhibitor(exemestane)was administered for 5 years. …
• NAID 120005435143

Related Links

• Exemestaneとは - goo Wikipedia (ウィキペディア)

Exemestane (trade name Aromasin) is a drug used to treat breast cancer. It is a member of the class of drugs known as aromatase inhibitors. Some breast cancers require estrogen to grow. Those cancers have estrogen receptors (ERs), and are called ER-positive.

• Exemestane - サプライヤーリスト - も用 1 4-Androstadien-3 17 ...

のサプライヤーのリストを取得する Exemestane と同等の製品を ... Gihi Chemicals Co., Ltd. ためのサプライヤです Exemestane. 私たちは、化学製品Methyl-1H-benzotriazole sodium saltを供給しています。

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アロマシン

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アロマターゼ阻害薬