Prinaberel

Prinaberel
Clinical data

ATC code	None
Identifiers
IUPAC name (4Z)-2-Fluoro-4-(5-hydroxy-7-vinyl-1,3-benzoxazol-2(3H)-ylidene)-2,5-cyclohexadien-1-one
CAS Number	524684-52-4
PubChem (CID)	5326893
ChemSpider	4484184
ECHA InfoCard	100.222.969
Chemical and physical data
Formula	C₁₅H₁₀FNO₃
Molar mass	271.243 g/mol
3D model (Jmol)	Interactive image
SMILES O=C3\C=C/C(=C2/Oc1c(cc(O)cc1N2)\C=C)/C=C3/F
InChI InChI=1S/C15H10FNO3/c1-2-8-5-10(18)7-12-14(8)20-15(17-12)9-3-4-13(19)11(16)6-9/h2-7,17-18H,1H2/b15-9- Key:FCXYSEXZEGPLGG-DHDCSXOGSA-N

Prinaberel (INN, USAN) (developmental code names ERB-041, WAY-202041) is a synthetic, non-steroidal, and highly selective agonist of the ERβ subtype of the estrogen receptor.^[1] It is used in scientific research to elucidate the role of the ERβ receptor.^[2] Studies have indicated that selective ERβ agonists like prinaberel could be useful in the clinical treatment of a variety of medical conditions including inflammatory bowel disease, rheumatoid arthritis, endometriosis, and sepsis.^[3] Accordingly, prinaberel either was or still is under investigation by Wyeth for the treatment of some of these conditions.^[4]

As of 2015, prinaberel is the only synthetic, selective ERβ agonist to have reached human clinical trials.^[5]

References

↑ Harris HA, Albert LM, Leathurby Y, et al. (October 2003). "Evaluation of an estrogen receptor-beta agonist in animal models of human disease". Endocrinology. 144 (10): 4241–9. doi:10.1210/en.2003-0550. PMID 14500559.
↑ Koehler KF, Helguero LA, Haldosén LA, Warner M, Gustafsson JA (May 2005). "Reflections on the discovery and significance of estrogen receptor beta". Endocrine Reviews. 26 (3): 465–78. doi:10.1210/er.2004-0027. PMID 15857973.
↑ Harris HA (2006). "Preclinical characterization of selective estrogen receptor beta agonists: new insights into their therapeutic potential". Ernst Schering Foundation Symposium Proceedings (1): 149–61. PMID 17824176.
↑ "Prinaberel - Wyeth phase change II, USA (endometriosis)". R & D Focus Drug News. 2006-06-05. Retrieved 2012-05-20.
↑ Narayanan, Ramesh; Dalton, James T. (2015). "Selective Estrogen Receptor Modulators (SERMs) and Selective Androgen Receptor Modulators (SARMs)": 205–227. doi:10.1007/978-3-319-18729-7_11.

External links

Prinaberel - AdisInsight

Estrogen receptor modulators

Agonists	Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin Abiraterone Abiraterone acetate 17α-Estradiol (alfatradiol) 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 DHEA DHEA-S Digitoxin (digitalis) Diosgenin Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin Estetrol Estradiol Estradiol 3-propionate Estradiol acetate Estradiol benzoate Estradiol butyrate benzoate Estradiol butyrylacetate Estradiol cyclooctyl acetate Estradiol cypionate Estradiol decanoate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol glucuronide Estradiol hemihydrate Estradiol hemisuccinate (estradiol succinate) Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol mustard Estradiol palmitate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol sulfate Estradiol undecylate Estradiol valerate Lipoidal estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol acetate benzoate Estriol glucuronide Estriol sodium succinate Estriol succinate Estriol sulfate Estriol sulfate glucuronide Estriol triacetate Estriol tripropionate Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone glucuronide Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol sulfonate Ethinyl estriol Etynodiol diacetate Guggulsterone Hexolame Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Noretynodrel Orestrate Pentolame Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prodiame Prolame Promestriene Quinestradol Quinestrol Non-steroidal: (R,R)-THC (S,S)-THC 1-Keto-1,2,3,4-tetrahydrophenanthrene 2,8-DHHHC Allenoic acid Alternariol Anethole Anol Benzestrol Bifluranol Biochanin A Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (dianisylhexene) Dimethylallenolic acid Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Endosulfan ERB-196 (WAY-202196) Estrobin (DBE) Fenarimol Fenestrel FERb 033 Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate ICI-85966 (Stilbostat) Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestilbol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methoxychlor Miroestrol Nyasol (cis-hinokiresinol) Paroxypropione Pentafluranol Phenestrol Photoanethole Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Quadrosilan SC-4289 SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Terfluranol WAY-166818 WAY-200070 Triphenylchlorethylene Triphenylmethylethylene WAY-214156

Mixed (SERMs)	27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epitiostanol Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LY-117018 Menerba Mepitiostane Methylepitiostanol Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Tamoxifen TAS-108 (SR-16234) Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Cytestrol acetate Fulvestrant (ICI-182780) ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) XCT-790 ZK-164015 ZK-191703

GPER

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Ethinyl estradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalanone Zearalenol Zearalenone Zeranol (zearalanol))

Antagonists	CCL18 Estriol G-15 G-36 MIBE

See also: Androgenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators

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