Cloxestradiol acetate

Cloxestradiol acetate
Systematic (IUPAC) name

[(8R,9S,13S,14S,17S)-17-(1-Acetyloxy-2,2,2-trichloroethoxy)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] acetate
Clinical data
Trade names	Genovul
Pregnancy category	X (Contraindicated)
Identifiers
CAS Number	15686-44-9
PubChem	CID 71586995
ChemSpider	34989697
Synonyms	1-{[(17β)-3-Acetoxyestra-1,3,5(10)-trien-17-yl]oxy}-2,2,2-trichloroethyl acetate
Chemical data
Formula	C₂₄H₂₉Cl₃O₅
Molar mass	503.84306 g/mol
SMILES CC(=O)OC1=CC2=C(C=C1)C3CCC4(C(C3CC2)CCC4OC(C(Cl)(Cl)Cl)OC(=O)C)C
InChI InChI=1S/C24H29Cl3O5/c1-13(28)30-16-5-7-17-15(12-16)4-6-19-18(17)10-11-23(3)20(19)8-9-21(23)32-22(24(25,26)27)31-14(2)29/h5,7,12,18-22H,4,6,8-11H2,1-3H3/t18-,19-,20+,21+,22?,23+/m1/s1 Key:UEVLJPRROXDIPO-CUFSGNDSSA-N

Cloxestradiol acetate (brand name Genovul) is a synthetic, steroidal estrogen derived from estradiol.^[1] It is the O,O-diacetate form of cloxestradiol, which, in contrast to cloxestradiol acetate, was never marketed.^[1]

References

1 2 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.

Estrogens and antiestrogens

Estrogens

Steroidal: Alfatradiol
Conjugated estrogens (Premarin)
Epimestrol
Esterified estrogens
Estetrol
Estradiol
- Cloxestradiol acetate
- Estradiol acetate
- Estradiol benzoate
- Estradiol butyrylacetate
- Estradiol cypionate^#
- Estradiol dipropionate
- Estradiol diundecylate
- Estradiol enanthate
- Estradiol furoate
- Estradiol hemihydrate
- Estradiol hemisuccinate
- Estradiol hexahydrobenzoate
- Estradiol monopropionate
- Estradiol palmitate
- Estradiol propoxyphenylpropionate
- Estradiol stearate
- Estradiol undecylate
- Estradiol valerate
- Estramustine
- Polyestradiol phosphate
- Trimethyl estradiol acetate
Estriol
- Estriol diacetate benzoate
- Estriol sodium succinate
- Estriol succinate
- Estriol triproprionate
- Quinestradol
Estrone
- Estrone acetate
- Estrone sulfate
  - Estropipate
- Estrone tetraacetylglucoside
Ethinyl estradiol^#
Etynodiol diacetate
Methylestradiol
Noretynodrel
Paroxypropione
Promestriene
Tibolone

Non-steroidal: Benzestrol
Dienestrol
Dienestrol acetate
Diethylstilbestrol
Diethylstilbestrol dipropionate
Doisynoestrol (fenocycline)
Hexestrol
Fosfestrol
Methallenestril
Methestrol dipropionate (promethestrol dipropionate)
Quadrosilan
Zeranol

Antiestrogens

SERMs / antagonists	SERMs: Anordrin Bazedoxifene Broparestrol Chlorotrianisene Clomifene citrate^# Cyclofenil Lasofoxifene Ormeloxifene Raloxifene Tamoxifen^# Toremifene Antagonists: Fulvestrant

Aromatase inhibitors	Non-selective: Aminoglutethimide Testolactone Selective: Anastrozole Exemestane Fadrozole Formestane Letrozole

Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, nandrolone, oxandrolone) GnRH agonists (e.g., leuprorelin) GnRH antagonists (e.g., cetrorelix) Progestogens (incl. allylestrenol, chlormadinone acetate, cyproterone acetate, delmadinone acetate, dydrogesterone, medroxyprogesterone acetate, megestrol acetate, nomegestrol acetate, norethisterone acetate, progesterone, spironolactone)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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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