D-15414

D-15414
Identifiers

IUPAC name 1-ethyl-2-(4-hydroxyphenyl)-3-methylindol-5-ol
CAS Number	86111-11-7^Y
PubChem CID	128800
ChemSpider	114137
UNII	58AE9Z8TW6
ChEMBL	ChEMBL287232
CompTox Dashboard (EPA)	DTXSID801006609
Chemical and physical data
Formula	C₁₇H₁₇NO₂
Molar mass	267.328 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN1C2=C(C=C(C=C2)O)C(=C1C3=CC=C(C=C3)O)C
InChI InChI=1S/C17H17NO2/c1-3-18-16-9-8-14(20)10-15(16)11(2)17(18)12-4-6-13(19)7-5-12/h4-10,19-20H,3H2,1-2H3 Key:BXTNOIWYTWIPEL-UHFFFAOYSA-N

D-15414 is a nonsteroidal weak estrogen of the 2-phenylindole group which was never marketed.^[1]^[2] It is the major metabolite of the selective estrogen receptor modulator (SERM) zindoxifene (D-16726).^[3] D-15414 has high affinity for the estrogen receptor (ER) and inhibits the growth of ER-positive MCF-7 breast cancer cells in vitro.^[3] However, contradictorily, subsequent research found that the drug produced fully estrogenic effects in vitro similarly to but less actively than estradiol, with no antiestrogenic activity observed.^[1]^[2] The reason for the discrepancy between the findings is unclear, though may be due to methodology.^[2] The unexpected estrogenic activity of D-15414 may be responsible for the failure of zindoxifene in clinical trials as a treatment for breast cancer.^[1]^[4]

References

^ ^a ^b ^c Jordan VC, Tormey DC (1988). "Antiestrogen Therapy for Breast Cancer". Endocrine Therapies in Breast and Prostate Cancer. Cancer Treatment and Research. Vol. 39. pp. 97–110. doi:10.1007/978-1-4613-1731-9_7. ISBN 978-1-4612-8974-6. PMID 2908611.
^ ^a ^b ^c Robinson SP, Koch R, Jordan VC (February 1988). "In vitro estrogenic actions in rat and human cells of hydroxylated derivatives of D16726 (zindoxifene), an agent with known antimammary cancer activity in vivo". Cancer Research. 48 (4): 784–787. PMID 3338076.
^ ^a ^b von Angerer E, Prekajac J, Berger M (April 1985). "The inhibitory effect of 5-acetoxy-2-(4-acetoxyphenyl)-1-ethyl-3-methylindole (D 16726) on estrogen-dependent mammary tumors". European Journal of Cancer & Clinical Oncology. 21 (4): 531–537. doi:10.1016/0277-5379(85)90048-3. PMID 3924626.
^ Maximov PY, McDaniel RE, Jordan VC (23 July 2013). Tamoxifen: Pioneering Medicine in Breast Cancer. Springer Science & Business Media. pp. 170–. ISBN 978-3-0348-0664-0.

Estrogen receptor modulators

Agonists	Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent-Estradiol Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Polyestriol phosphate Estrofurate Estrogenic substances Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Nonsteroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2 (GTx-878) AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Dimethylstilbestrol Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Elacestrant ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-3296 SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688 (SIM-688) WAY-214156 Unknown/unsorted: ERB-26 ERA-45 ERB-79 ZK-283197 Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole) Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Lavender oil Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol)) Metalloestrogens (e.g., cadmium) Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan) Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone) Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Steroid-like (e.g., deoxymiroestrol, miroestrol) Stilbenoids (e.g., resveratrol, rhaponticin) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Others (e.g., agnuside, rotundifuran)
Mixed (SERMsTooltip Selective estrogen receptor modulators)	2-Phenylbenzofuran 2-Phenylbenzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Camizestrant Chlorotrianisene Clomifene Clomifenoxide CN-55945-27 Cyclofenil D-15413 Desmethylchlorotrianisene Droloxifene Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate MRL-37 Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil (P-081) Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 U-11555A U-11634 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 (SCH-57050) Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 MDL-101906 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-binding modulators: ERX-11 Noncompetitive inhibitors: Trilostane

GPER

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

Read other articles:

Nyak Adam Kamil

Artikel ini tidak memiliki referensi atau sumber tepercaya sehingga isinya tidak bisa dipastikan. Tolong bantu perbaiki artikel ini dengan menambahkan referensi yang layak. Tulisan tanpa sumber dapat dipertanyakan dan dihapus sewaktu-waktu.Cari sumber: Nyak Adam Kamil – berita · surat kabar · buku · cendekiawan · JSTOR Nyak Adam Kamil Gubernur Daerah Istimewa Aceh ke-8Masa jabatan10 April 1964 – 30 Agustus 1966 PendahuluAli HasjmyPenggan...

Salat Witir

Bagian dari seriIslam Rukun Iman Keesaan Allah Malaikat Kitab-kitab Allah Nabi dan Rasul Allah Hari Kiamat Qada dan Qadar Rukun Islam Syahadat Salat Zakat Puasa Haji Sumber hukum Islam al-Qur'an Sunnah (Hadis, Sirah) Tafsir Akidah Fikih Syariat Sejarah Garis waktu Muhammad Ahlulbait Sahabat Nabi Khulafaur Rasyidin Khalifah Imamah Ilmu pengetahuan Islam abad pertengahan Penyebaran Islam Penerus Muhammad Budaya dan masyarakat Akademik Akhlak Anak-anak Dakwah Demografi Ekonomi Feminisme Filsafat...

Kehidupan nyata

Kerumanan orang di Shibuya, Tokyo. Kehidupan nyata atau dunia nyata adalah frasa yang mulanya digunakan dalam sastra untuk membedakan antara dunia nyata dan rekaan atau dunia ideal, dan dalam drama untuk membedakan pemain asli dan karakter yang diperankan. Belakangan ini, frasa ini juga digunakan untuk membedakan antara kejadian atau orang yang ditemui di dunia nyata dan di dunia maya atau internet. Pembeda dari dunia maya Dalam dunia maya, kehidupan nyata berarti kehidupan luar jaringan atau...

فيتالي كليتشكو

فيتالي كليتشكو (بالأوكرانية: Віталій Володимирович Кличко)‏ معلومات شخصية الميلاد 19 يوليو 1971 (العمر 52 سنة) الإقامة كييف مواطنة الاتحاد السوفيتي أوكرانيا الطول 2.01 متر الوزن 114 كيلوغرام عدد الأولاد 4 إخوة وأخوات فلاديمير كليتشكو مناصب نائب الشعب الأو...

ماريان نغوابي

ماريان نغوابي (بالفرنسية: Marien Ngouabi)‏ معلومات شخصية الميلاد 31 ديسمبر 1938(1938-12-31)أواندو [لغات أخرى]‏ الوفاة 18 مارس 1977 (38 سنة) برازافيل مكان الدفن أواندو [لغات أخرى]‏ مواطنة جمهورية الكونغو عدد الأولاد 1 مناصب رئيس جمهورية الكونغو �...

Char kway teow

Char kway teow Hanzi tradisional: 炒粿條 Hanzi sederhana: 炒粿条 Makna harfiah: kwetiau goreng Alih aksara Mandarin - Hanyu Pinyin: cháo guǒ tiáo Min Nan - Romanisasi POJ: chhá-kóe-tiâu Yue (Kantonis) - Jyutping: caau2 gwo2 tiu4 Nama alternatif dikawasan berbahasa Kanton Hanzi tradisional: 炒貴刁 Hanzi sederhana: 炒贵刁 Makna literal: tidak ada Alih aksara Mandarin - Hanyu Pinyin: cháo guì diāo Yue (Kantonis) - Jyutping: caau2 gwai3 diu1 Char kway teowJenisShahe fenTempa...

Piala Italia 2021–2022

Piala Italia 2021–2022NegaraItaliaTanggal penyelenggaraan7 Agustus 2021 – 11 Mei 2022Jumlah peserta44JuaraInter Milan(gelar ke-8)Tempat keduaJuventusJumlah pertandingan46Jumlah gol156 (3.39 per pertandingan)Pencetak gol terbanyakDušan Vlahović(4 gol)← 2020–2021 2022–2023 → Piala Italia 2021–2022 adalah edisi ke–75 Piala Italia, kompetisi nasional sepak bola di Italia.[1] Jumlah tim yang berpartisipasi dikurangi dari 78 pada musim sebelumnya menjadi hanya 44 klub.[...

Zhelyu Zhelev

Zhelyu Mitev Zhelev Желю Митев Желев Presiden Republik Bulgaria Ke-2Masa jabatan1 Agustus 1990 – 22 Januari 1997Wakil PresidenBlaga DimitrovaPendahuluPetar MladenovPenggantiPetar Stoyanov Informasi pribadiLahir(1935-03-03)3 Maret 1935VeselinovoMeninggal30 Januari 2015(2015-01-30) (umur 79)KebangsaanBulgariaPartai politikUDFSuami/istriMaria ZhelevaSunting kotak info • L • B Zhelyu Mitev Zhelev (bahasa Bulgaria: Желю Митев Желев; 3 M...

Movies!

American classic movie television network This article is about the television channel. For other uses, see Movie (disambiguation). Television channel Movies!TypeFree-to-air television network(movies and television programs)CountryUnited StatesBroadcast areaNationwide via digital terrestrial television (U.S. coverage: 61%)[1] and streamingHeadquartersChicago, IllinoisProgrammingPicture format480i (SDTV)(transmitted in either 16:9 widescreen or 4:3 letterbox)OwnershipOwnerFox Corporati...

Berryz Kobo

Berryz Kobo Paese d'origine Giappone GenereJ-pop Periodo di attività musicale2004 – 2015 EtichettaPiccolo Town Album pubblicati10 Studio8 Raccolte2 Sito ufficiale Modifica dati su Wikidata · Manuale Le Berryz Kobo (Berryz工房?, Berīzu Kōbō, letteralmente «Laboratorio delle Berryz») sono un gruppo femminile di idol giapponesi. Fanno parte del Hello! Project. La musica ed i testi di quasi tutte le loro canzoni sono scritti da Tsunku, il fondatore e pr...

Okular

Document viewer by KDE OkularOkular showing a PDF in KDE Plasma 5Original author(s)Piotr SzymańskiDeveloper(s)KDEInitial release2005; 19 years ago (2005)[1][2]Stable release24.02.1[3] / 19 March 2024Preview release21.11.90[4] / 24 November 2021 Repositoryinvent.kde.org/graphics/okular Written inC++Operating systemLinux, Unix-like, WindowsTypeUniversal document viewerLicenseGPL-2.0-only or GPL-3.0-onlyWebsiteokular.kde.org Okular i...

Кубок наций Персидского залива по футболу 1970

Кубок наций Персидского залива по футболу1970 Gulf Cup of Nations Подробности чемпионата Место проведения Бахрейн Сроки турнира 27 марта — 3 апреля Число участников 4 Чемпион Кувейт Статистика чемпионата Сыграно матчей 6 Забито голов 19 (3,17 за игру) Бомбардир(ы) Мухаммед аль-Ма�...

Symmetric power

This article relies largely or entirely on a single source. Relevant discussion may be found on the talk page. Please help improve this article by introducing citations to additional sources.Find sources: Symmetric power – news · newspapers · books · scholar · JSTOR (April 2024) This article may lack focus or may be about more than one topic. Please help improve this article, possibly by splitting the article and/or by introducing a disambiguation page...

نائب رئيس الولايات المتحدة

نائب رئيس الولايات المتحدة (بالإنجليزية: Vice President of the United States)‏ نائب رئيس الولايات المتحدةعلم نائب الرئيس الأمريكي نائب رئيس الولايات المتحدةشعار نائب الرئيس الأمريكي شاغل المنصب كامالا هاريس منذ 20 يناير 2021 البلد الولايات المتحدة اللقب نائب الرئيس الأمريكي عن ...

Expédition de Djidjelli

Expédition de Djidjelli (1664) Gravure d'époque représentant le débarquement français à Djidjelli (alias Gigeri) Informations générales Date 22 juillet - 31 octobre 1664 Lieu Djidjelli (Régence d'Alger) Issue Victoire de la Régence d'Alger et ses alliés, abandon de Djidjelli et naufrage de La Lune Belligérants Royaume de France Hospitaliers • Régence d'Alger • Royaume des Beni Abbès• Royaume de Koukou Commandants • Louis XIV• François de Vendôme• Charles-Félix de...

山口朝日放送

この記事には複数の問題があります。改善やノートページでの議論にご協力ください。出典がまったく示されていないか不十分です。内容に関する文献や情報源が必要です。（2015年10月）独自研究が含まれているおそれがあります。（2015年10月）あまり重要でない事項が過剰に含まれているおそれがあり、整理が求められています。（2015年10月）出典検索?: 山口朝...

New Left

Questa voce o sezione sull'argomento storia è ritenuta da controllare. Motivo: assenza di note e tendenziosità Partecipa alla discussione e/o correggi la voce. Segui i suggerimenti del progetto di riferimento. Vietato vietare, celebre slogan usato dalla sinistra radicale degli anni sessanta, essenzialmente d'impronta situazionista New Left (Nuova Sinistra) è un'espressione utilizzata per indicare quei movimenti emersi dalla controcultura anni '60, nonché di sinistra radicale, che ha...

Wedding of Prince Charles and Camilla Parker Bowles

2005 British royal wedding Wedding of Prince Charles and Camilla Parker BowlesCombined coat of arms the Prince of Wales and the Duchess of CornwallDate9 April 2005; 19 years ago (9 April 2005)VenueWindsor GuildhallSt George's Chapel, Windsor CastleLocationWindsor, Berkshire, EnglandParticipantsCharles, Prince of Wales (later King Charles III)Camilla Parker Bowles (later Queen Camilla) The wedding of Prince Charles and Camilla Parker Bowles (later King Charles III and Queen Camill...

Voiced bilabial fricative

Consonantal sound represented by ⟨β⟩ in IPA Voiced bilabial fricativeβIPA Number127Audio sample source · helpEncodingEntity (decimal)βUnicode (hex)U+03B2X-SAMPABBraille Image Voiced bilabial approximantβ̞ʋ̟Audio sample source · help The voiced bilabial fricative is a type of consonantal sound, used in some spoken languages. The symbol in the International Phonetic Alphabet that represents this sound is ⟨β⟩, and the equivalent X-SAM...

Louis Artus

French playwright (1870-1960) Louis ArtusBorn10 January 18708th arrondissement of ParisDied11 May 1960(1960-05-11) (aged 90)6th arrondissement of ParisOccupation(s)Writer, dramatist Louis Artus (10 January 1870 - 11 May 1960) [1] was a French writer. A dramatist, playwright, novelist and critic, Artus began his career with parts in verse such as La Duchesse Putiphar. After studying with the Jesuits (in France and England), Artus, who regularly attended literary circles, collabora...