Cloxestradiol

Cloxestradiol
Systematic (IUPAC) name

(8R,9S,13S,14S,17S)-13-Methyl-17-(2,2,2-trichloro-1-hydroxyethoxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
Identifiers
CAS Number	54063-33-1
PubChem	CID 194705
Synonyms	17-(1-Hydroxy-2,2,2-trichloroethoxy)estra-1,3,5(10-trien-3-ol
Chemical data
Formula	C₂₀H₂₅Cl₃O₃
Molar mass	419.7697 g/mol
SMILES CC12CCC3C(C1CCC2OC(C(Cl)(Cl)Cl)O)CCC4=C3C=CC(=C4)O

Cloxestradiol (INN) is a synthetic, steroidal estrogen that was never marketed.^[1] It is an analogue of estradiol with a 2,2,2-trichloroethoxy substitution.^[1]

The O,O-diacetate derivative, cloxestradiol acetate (brand name Genovul), has been marketed as an estrogen.^[1]

References

1 2 3 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 308–. ISBN 978-1-4757-2085-3.

Estrogenics

Receptor
(ligands)

ER (α, β)

Agonists	(R)-DPN (S)-DPN (R,R)-THC (S,S)-THC 2,8-DHHHC 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 7-Oxo-DHEA 7α-Hydroxy-DHEA 7β-Hydroxyepiandrosterone 8β-VE₂ 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-IE₂ 16α-LE₂ (Cpd1471) Δ⁴-Androstenedione Δ⁵-Androstenediol 17α-Estradiol (alfatradiol) 17β-Estradiol (estradiol) Alestramustine Almestrone Anabolic steroids (prodrugs; e.g., testosterone, metandienone (methandrostenolone), others) Anethole Anol Atrimustine Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Cloxestradiol Conjugated equine estrogens (e.g., sodium equilin sulfate, sodium equilenin sulfate) Coumestans (e.g., coumestrol, psoralidin) DHEA DHEA-S Deoxymiroestrol Dianethole Dianol Diarylpropionitrile Dieldrin Dienestrol Dienestrol acetate Diethylstilbestrol Diethylstilbestrol dipropionate Diosgenin Doisynoestrol (fenocycline) Doisynolic acid DY-131 (GSK-9089) Endosulfan Epiestriol Epimestrol ERB-196 (WAY-202196) Esterified estrogens (e.g., estrone sulfate, equilin sulfate, equilenin sulfate) Estetrol Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate Estradiol dienanthate Estradiol dipropionate Estradiol diundecylate Estradiol diundecylenate Estradiol enanthate Estradiol furoate Estradiol hemihydrate Estradiol hemisuccinate Estradiol hexahydrobenzoate Estradiol monopropionate Estradiol palmitate Estradiol pivalate Estradiol propoxyphenylpropionate Estradiol stearate Estradiol succinate Estradiol undecylate Estradiol valerate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol succinate Estriol tripropionate Estrobin (DBE) Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Estropronicate Etamestrol (eptamestrol) Ethinyl estradiol Ethinyl estradiol 3-isopropylsulfonate Etynodiol diacetate 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 Furostilbestrol GSK-4716 Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Lavender oil Lignans (e.g., enterodiol, enterolactone) Mestranol Metalloestrogens (e.g., cadmium) Methallenestril Methestrol Methestrol dipropionate Methiocarb Methylestradiol Miroestrol Moxestrol Nilestriol Noretynodrel Orestrate Paroxypropione Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Polyestradiol phosphate Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Promestriene Resorcylic acid lactones (e.g., zearalanone, zearalenol, zearalenone, zeranal (zearalanol)) Quadrosilan Quinestradol Quinestrol SKF-82,958 Stilbenoids (e.g., resveratrol) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) WAY-166818 WAY-200070

Mixed (SERMs)	2-Hydroxyestrone 27-Hydroxycholesterol Acolbifene Afimoxifene Anordrin Anordriol Arzoxifene Bazedoxifene Broparestrol Chlorotrianisene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Phenytoin Pipendoxifene Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene

Antagonists	(R,R)-THC Fulvestrant ICI-164384 Methylpiperidinopyrazole MIBE PHTPP Prochloraz RU-58668 SS1020 XCT-790 ZK-164015 ZK-191703

GPER

Agonists	7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Fulvestrant (ICI-182,780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCB (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalenone

Antagonists	Estriol G-15 G-36 MIBE

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, aromatase, and 27-hydroxylase).

Others

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate 16-Hydroxy-DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione 16-Hydroxyandrostenedione Testosterone

Indirect	Antigonadotropins (e.g., androgens, estrogens, progestogens, prolactin) Calcitriol (vitamin D) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Androgenics • Glucocorticoids • Mineralocorticoids • Progestogenics

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