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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/16 19:50:41」(JST)

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Toremifene citrate is an oral selective estrogen receptor modulator (SERM) which helps oppose the actions of estrogen in the body. Licensed in the United States under the brand name Fareston, toremifene citrate is FDA-approved for use in advanced (metastatic) breast cancer. It is also being evaluated for prevention of prostate cancer under the brand name Acapodene.^[1]

In 2007 the pharmaceutical company GTx, Inc was conducting two different phase 3 clinical trials; First, a pivotal Phase clinical trial for the treatment of serious side effects of androgen deprivation therapy (ADT) (especially vertebral/spine fractures and hot flashes, lipid profile, and gynecomastia) for advanced prostate cancer, and second, a pivotal Phase III clinical trial for the prevention of prostate cancer in high risk men with high grade prostatic intraepithelial neoplasia, or PIN. Results of these trials are expected by first quarter of 2008^[2]

An NDA for the first application (relief of prostate cancer ADT side effects) was submitted in Feb 2009,^[3] and in Oct 2009 the FDA said they would need more clinical data, e.g. another phase III trial.^[4]

Synthesis

Toremifene synthesis: U.S. Patent 4,696,949

References

^ Price N, Sartor O, Hutson T, Mariani S. Role of 5a-reductase inhibitors and selective estrogen receptor modulators as potential chemopreventive agents for prostate cancer. Clin Prostate Cancer 2005;3:211-4. PMID 15882476
^ "GTx's Phase III Clinical Development of ACAPODENE on Course Following Planned Safety Review" (Press release). GTx Inc. 2007-07-12. Retrieved 2006-07-14.
^ "GTx Announces Toremifene 80 mg NDA Accepted for Review by FDA" (Press release).
^ "GTx and Ipsen End Prostate Cancer Collaboration due to Costs of FDA-Requested Phase III Study". 2 Mar 2011.

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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. 前立腺癌における化学的予防策 chemoprevention strategies in prostate cancer
3. デスモイド腫瘍：全身療法 desmoid tumors systemic therapy
4. 悪性腫瘍患者における薬物誘発性血栓症 drug induced thrombosis in patients with malignancy
5. 前立腺の前癌病変：病理および臨床的意義 precancerous lesions of the prostate pathology and clinical implications

English Journal

Clinically used selective estrogen receptor modulators affect different steps of macrophage-specific reverse cholesterol transport.

Fernández-Suárez ME1,2, Escolà-Gil JC3,4,5, Pastor O2,6, Dávalos A7, Blanco-Vaca F3,4,5, Lasunción MA1,2, Martínez-Botas J1,2, Gómez-Coronado D1,2.
Scientific reports.Sci Rep.2016 Sep 7;6:32105. doi: 10.1038/srep32105.
Selective estrogen receptor modulators (SERMs) are widely prescribed drugs that alter cellular and whole-body cholesterol homeostasis. Here we evaluate the effect of SERMs on the macrophage-specific reverse cholesterol transport (M-RCT) pathway, which is mediated by HDL. Treatment of human and mouse
PMID 27601313

Clinical significance of fatty liver disease induced by tamoxifen and toremifene in breast cancer patients.

Yang YJ1, Kim KM2, An JH1, Lee DB1, Shim JH1, Lim YS1, Lee HC1, Lee YS1, Ahn JH3, Jung KH3, Kim SB3.
Breast (Edinburgh, Scotland).Breast.2016 Aug;28:67-72. doi: 10.1016/j.breast.2016.04.017. Epub 2016 May 27.
BACKGROUND AND AIM: The aim of this study was to identify the effect of selective estrogen receptor modulator (SERM) on non-alcoholic fatty liver disease (NAFLD) in Asian women.METHODS: We retrospectively evaluated fatty liver development and/or serum alanine aminotransferase (ALT) elevation during
PMID 27240168

Toremifene interacts with and destabilizes the Ebola virus glycoprotein.

Zhao Y, Ren J, Harlos K, Jones DM, Zeltina A, Bowden TA, Padilla-Parra S, Fry EE, Stuart DI.
Nature.Nature.2016 Jul 7;535(7610):169-72.
Ebola viruses (EBOVs) are responsible for repeated outbreaks of fatal infections, including the recent deadly epidemic in West Africa. There are currently no approved therapeutic drugs or vaccines for the disease. EBOV has a membrane envelope decorated by trimers of a glycoprotein (GP, cleaved by fu
PMID 27362232

Japanese Journal

乳癌治療後に妊娠・分娩に至った２例

中村光佐子,古板規子,藁谷深洋子,富永愛,藤田琢史
産婦人科の進歩 63(3), 301-306, 2011
近年，癌治療の進歩によりcancer survivorという言葉が使われるようになってきた．白血病や乳癌など，若年に多い癌のsurvivorの妊孕性と妊娠・分娩・母乳哺育による原疾患への影響について検討した報告は多くない．今回，当院の乳腺外科で治療を受けた乳癌患者で，その後に妊娠・分娩に至った症例を2例経験したので報告する．<症例1>乳腺外科初診時32歳，4回経妊4回経産．第5子妊娠時 …
NAID 130001222819

PROSPECTIVE STUDY ON THE EFFECT OF TOREMIFENE IN PATIENTS WITH ADJUVANT ANASTROZOLE FAILURE IN POSTMENOPAUSAL BREAST CANCER

Nishimura Reiki,Nakamura Seigo,Oba Koji,Komoike Yoshifumi,Mitsuyama Shoshu,Hisamatsu Kazufumi,Oriuchi Noboru,Abe Chigusa,Kuwayama Takashi,Taguchi Tetsuya,Sakamoto Junichi,Noguchi Shinzaburo
Annals of Cancer Research and Therapy 19(1), 9-14, 2011
… Postmenopausal patients who relapsed during adjuvant AI treatment or progression within a year after completion of AI treatment were prospectively treated with 40 mg/day of toremifene (TOR) in order to examine the effect of the selective estrogen receptor modulator (SERM) in AI-refractory patients. … All patients were treated with toremifene of 40 mg/day. … The SERM, toremifene (40 mg/day), demonstrated a safe profile and a favorable effect on disease control after adjuvant AI failure. …
NAID 130000400028

Clinical usefulness of high-dose toremifene in patients relapsed on treatment with an aromatase inhibitor

YAMAMOTO Yutaka,MASUDA Norikazu,OHTAKE Tohru,YAMASHITA Hiroko,SAJI Shigehira,KIMIJIMA Izo,KASAHARA Yoshio,ISHIKAWA Takashi,SAWAKI Masataka,HOZUMI Yasuo,IWASE Hirotaka
Breast cancer : the journal of the Japanese Breast Cancer Society 17(4), 254-260, 2010-10-01
NAID 10027509334

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★リンクテーブル★

リンク元	「トレミフェン」
拡張検索	「toremifene citrate」

「トレミフェン」

Toremifene
Systematic (IUPAC) name
	2-{4-[(1Z)-4-chloro-1,2-diphenyl-but-1-en-1-yl]phenoxy}-N,N-dimethylethanamine
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a608003
Pharmacokinetic data
Protein binding	more than 99.5%
Half-life	5 days
Identifiers
CAS Registry Number	89778-26-7
ATC code	L02BA02
PubChem	CID 3005573
DrugBank	DB00539
ChemSpider	2275722
UNII	7NFE54O27T
KEGG	D08620
ChEBI	CHEBI:9635
ChEMBL	CHEMBL1655
Chemical data
Formula	C26H28ClNO
Molecular mass	405.959 g/mol
	SMILES ClCCC(/c1ccccc1)=C(/c2ccc(OCCN(C)C)cc2)c3ccccc3;
	InChI InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25- ; Key:XFCLJVABOIYOMF-QPLCGJKRSA-N ;
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