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Chemical compound
Pharmaceutical compound
Miproxifene |
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| Other names | DP-TAT-59 |
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4-[(Z)-1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-(4-propan-2-ylphenyl)but-1-enyl]phenol
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| Formula | C29H35NO2 |
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| Molar mass | 429.604 g·mol−1 |
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| 3D model (JSmol) | |
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CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=C(C=C3)C(C)C
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InChI=1S/C29H35NO2/c1-6-28(23-9-7-22(8-10-23)21(2)3)29(24-11-15-26(31)16-12-24)25-13-17-27(18-14-25)32-20-19-30(4)5/h7-18,21,31H,6,19-20H2,1-5H3/b29-28- Key:FVVPWVFWOOMXEZ-ZIADKAODSA-N
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Miproxifene (INN) (former developmental code name DP-TAT-59) is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that was never marketed.[1][2] It is a derivative of afimoxifene (4-hydroxytamoxifen) in which an additional 4-isopropyl group is present in the β-phenyl ring.[3] The drug has been found to be 3- to 10-fold more potent than tamoxifen in inhibiting breast cancer cell growth in in vitro models.[1][4][5] Miproxifene is the active metabolite of miproxifene phosphate (TAT-59), a phosphate ester and prodrug of miproxifene that was developed to improve its water solubility.[1][2][6][7] Miproxifene phosphate was under development for the treatment of breast cancer and reached phase III clinical trials for this indication but development was discontinued.[1]
- ^ a b c d "Miproxifene". AdisInsight. Springer Nature Switzerland AG.
- ^ a b Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J (12 March 2007). Prodrugs: Challenges and Rewards. Springer Science & Business Media. pp. 168–169. ISBN 978-0-387-49782-2.
- ^ Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens. Springer Science & Business Media. pp. 58–60. ISBN 978-3-642-58616-3.
- ^ Kelloff GJ, Hawk ET, Sigman CC (17 August 2008). Cancer Chemoprevention: Volume 2: Strategies for Cancer Chemoprevention. Springer. pp. 251–. ISBN 978-1-59259-768-0.
- ^ Ottow E, Weinmann H (8 September 2008). Nuclear Receptors as Drug Targets. John Wiley & Sons. pp. 90–. ISBN 978-3-527-62330-3.
- ^ Stromgaard K, Krogsgaard-Larsen P, Madsen U (19 August 2016). Textbook of Drug Design and Discovery, Fifth Edition. CRC Press. pp. 162–. ISBN 978-1-4987-0279-9.
- ^ Yang HC, Yeh WK, McCarthy JR (22 November 2013). Enzyme Technologies: Pluripotent Players in Discovering Therapeutic Agent. Wiley. pp. 166–. ISBN 978-1-118-73989-1.
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| ERTooltip Estrogen receptor | | 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
- 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
- Estramustine
- Estramustine phosphate
- Estrapronicate
- Estrazinol
- Estriol
- Estrofurate
- Estrogenic substances
- Estromustine
- Estrone
- Etamestrol (eptamestrol)
- Ethinylandrostenediol
- Ethinylestradiol
- 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
- 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)
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Mixed
(SERMsTooltip Selective estrogen receptor modulators) | |
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| Antagonists |
- Coregulator-binding modulators: ERX-11
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| GPERTooltip G protein-coupled estrogen receptor | | Agonists | |
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| Antagonists | |
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| Unknown | |
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