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Chemical compound
Pharmaceutical compound
Pipendoxifene |
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Other names | ERA-923 |
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2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol
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Formula | C29H32N2O3 |
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Molar mass | 456.586 g·mol−1 |
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3D model (JSmol) | |
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CC1=C(N(C2=C1C=C(C=C2)O)CC3=CC=C(C=C3)OCCN4CCCCC4)C5=CC=C(C=C5)O
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InChI=1S/C29H32N2O3/c1-21-27-19-25(33)11-14-28(27)31(29(21)23-7-9-24(32)10-8-23)20-22-5-12-26(13-6-22)34-18-17-30-15-3-2-4-16-30/h5-14,19,32-33H,2-4,15-18,20H2,1H3 Key:JICOGKJOQXTAIP-UHFFFAOYSA-N
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Pipendoxifene (INN) (developmental code name ERA-923) is a nonsteroidal selective estrogen receptor modulator (SERM) that was under development by Ligand Pharmaceuticals and Wyeth-Ayerst Laboratories (now Wyeth) for the treatment of breast cancer but was not marketed.[1][2][3] It is a member of the 2-phenylindole group of SERMs and is structurally related to zindoxifene and the marketed bazedoxifene.[2][3] The drug reached phase II clinical trials before its development was discontinued.[1][2] It was synthesized at the same time as bazedoxifene and was intended as a backup drug for bazedoxifene, only to be developed further if bazedoxifene had failed in clinical trials.[1][2] No further development was reported after 2002 and it was formally announced that development had been terminated in November 2005.[1][4]
Unlike the SERM raloxifene, pipendoxifene is devoid of uterotrophic activity in immature/ovariectomized rodents.[3][5]
References
External links
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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
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- 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)
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- 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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