Quinestrol

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Quinestrol

Systematic (IUPAC) name
(17β)-3-(cyclopentyloxy)-17-ethynylestra-1,3,5(10)-trien-17-ol
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Legal status	?
Identifiers
CAS number	152-43-2^Y
ATC code	None
PubChem	CID 9046
DrugBank	DB04575
ChemSpider	8694^Y
UNII	JR0N7XD5GZ^Y
KEGG	D00576^Y
ChEBI	CHEBI:8716^Y
ChEMBL	CHEMBL1201165^N
Synonyms	3-Cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
Chemical data
Formula	C₂₅H₃₂O₂
Mol. mass	364.52 g/mol
SMILES O(c1ccc2c(c1)CC[C@H]3[C@@H]4CC[C@](C#C)(O)[C@@]4(C)CC[C@H]23)C5CCCC5
InChI InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3/t21-,22-,23+,24+,25+/m1/s1^Y Key:PWZUUYSISTUNDW-VAFBSOEGSA-N^Y
N (what is this?) (verify)

Quinestrol (ethinyl estradiol 3-cyclopentyl ether) is synthetic estrogen used in hormone replacement therapy, and occasionally to treat breast cancer and prostate cancer.

References

Estrogens and progestogens (G03C-D, L02)

Progestogens

Agonist

1st	Norpregnene Norethisterone^#/Norethisterone acetate Etynodiol diacetate

2nd	Norpregnene Levonorgestrel^#/Norgestrel/Norelgestromin

3rd	19-Nortestosterone Desogestrel/Etonogestrel Gestodene Norgestimate

4th	Androstene Drospirenone 19-Norprogesterone Nomegestrol acetate Promegestone Trimegestone 19-Nortestosterone Dienogest

17-OH	Chlormadinone acetate Cyproterone acetate Medroxyprogesterone acetate^# Megestrol acetate

Other/ ungrouped	Pregnenedione Gestonorone Pregnene Ethisterone Pregnadiene Medrogestone Norpregnane Norgestrienone Lynestrenol Norethynodrel Tibolone Dydrogesterone Quingestanol

Antiprogestogens/
SPRMs

Antagonists
- Aglepristone
- Mifepristone

Estrogens

Agonists

Steroidal	Diosgenin Estetrol Estradiol Estradiol acetate Estradiol benzoate Estradiol cypionate^# Estradiol dipropionate Estradiol enanthate Estradiol hemihydrate Estradiol undecylate Estradiol valerate Polyestradiol phosphate Estriol Estriol succinate Estrone Estrone sulfate Estriol Ethinylestradiol^# Mestranol Promestriene Equilenin Equilin

Nonsteroidal	Chlorotrianisene Dienestrol Fosfestrol Diethylstilbestrol Zeranol

Antiestrogens/
SERMs

Pure antagonists: Fulvestrant

Aromatase inhibitors

Nonselective: Aminoglutethimide; Testolactone

Selective: Anastrozole; Atamestane; Exemestane; Fadrozole; Formestane; Letrozole; Minamestane; Plomestane; Vorozole

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

M: ♀ FRS

anat/phys/devp

noco/cong/npls, sysi/epon

proc/asst, drug (G1/G2B/G3CD)

Estrogenics

Receptor

ER (α, β)	Agonists: 5α-Androstane-3β,17β-diol 16α-Hydroxyestrone Alestramustine Almestrone Benzestrol Bifluranol Broparestrol Carbestrol Chlorotrianisene Cloxestradiol Daidzein DHEA Dienestrol Diethylstilbestrol Diethylstilbestrol diphosphate Diosgenin Doisynoestrol DPN Epiestriol Epimestrol Eptamestrol/Etamestrol ERB-041 Equilenin Equilin Estetrol Estradiol 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 Estrofurate Estromustine Estrone Estrone acetate Estrone cyanate Estrone sulfate Estrone tetraacetylglucoside Estropipate Etamestrol Ethinylestradiol Ethinylestradiol 3-isopropylsulfonate Etynodiol diacetate FERb 033 Fenestrel Fosfestrol Furostilbestrol Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Hydroxyestrone diacetate Liquiritigenin Mestranol Methallenestril Methestrol Methestrol dipropionate Moxestrol Nilestriol Orestrate Polyestradiol phosphate PPT Promestriene Promethoestrol Quinestradol Quinestrol β-Sitosterol WAY-200,070 Note: Though not listed here, many anabolic steroids can also be estrogenic as they can be aromatized into estrogen-like metabolites that possess estrogenic activity. Mixed (SERMs): 2-Hydroxyestrone Acolbifene Afimoxifene Arzoxifene Bazedoxifene Clomifene Clomifenoxide Cyclofenil Droloxifene Enclomifene Endoxifen Epimestrol Femarelle Fispemifene GW5638 Idoxifene Lasofoxifene Levormeloxifene Menerba Mepitiostane Miproxifene Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Prinaberel Raloxifene SS1010 Sivifene Tamoxifen TAS-108 Tesmilifene Tibolone Toremifene Trioxifene Y-134 Zindoxifene Zuclomifene Antagonists: Fulvestrant ICI-164,384 MPP PHTPP RU-58,668 SS1020 ZK-164,015 ZK-191,703 Note: Xenoestrogens (e.g., phytoestrogens and mycoestrogens) are not included here. For a full list of xenoestrogens, see here.

GPER	Agonists: Estradiol Fulvestrant G-1 Genistein Quercetin Tamoxifen Antagonists: G-15

Enzyme
(inhibitors)

20,22-Desmolase	22-ABC 3,3′-Dimethoxybenzidine 3-Methoxybenzidine Aminoglutethimide Cyanoketone Danazol Etomidate Mitotane Trilostane

17α-Hydroxylase, 17,20-Lyase	22-ABC 22-Oxime Abiraterone Bifonazole Clotrimazole Cyanoketone Cyproterone Danazol Econazole Galeterone Gestrinone Isoconazole Ketoconazole L-39 Liarozole LY-207,320 MDL-27,302 Miconazole Mifepristone Orteronel Pioglitazone Rosiglitazone Spironolactone Stanozolol SU-10,603 TGF-β Tioconazole Troglitazone VN/87-1 YM116

3β-HSD	4-MA Azastene Cyanoketone Danazol Epostane Genistein Gestrinone Metyrapone Oxymetholone Pioglitazone Rosiglitazone Trilostane Troglitazone

17β-HSD	Danazol Simvastatin

Aromatase	1,4,6-Androstatriene-3,17-dione 4-Androstene-3,6,17-trione 4-Cyclohexylaniline 4-Hydroxytestosterone 5α-DHNET Abyssinone II Aminoglutethimide Anastrozole Ascorbic acid (Vitamin C) Atamestane Bifonazole CGP-45,688 CGS-47,645 Clotrimazole DHT Difeconazole Econazole Exemestane Fadrozole Fenarimol Finrozole Formestane Imazalil Isoconazole Ketoconazole Letrozole Liarozole MEN-11066 Miconazole Minamestane Nimorazole NKS01 ORG-33,201 Penconazole Plomestane Prochloraz Propioconazole Pyridoglutethimide Rogletimide Rotenone Talarozole Testolactone Tioconazole Triadimefon Triadimenol Troglitazone Vorozole YM511 Zinc Note: 5α-reductase and 21-hydroxylase inhibitors may also affect estrogen levels as they prevent metabolism of estrogen steroid precursors.

Other

Endogenous	Estrogens: 5α-Androstane-3β,17β-diol DHEA Estetrol Estradiol Estriol Estrone Antiestrogens: 2-Hydroxyestrone 16-Hydroxyestrone Precursors: Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone Cortodoxone/Deoxycortisol DHEA DHEA sulfate 16-Hydroxy-DHEA 16-Hydroxy-DHEA sulfate Androstenediol Androstenedione 16-Hydroxyandrostenedione Testosterone

Indirect	Androgens/Antiandrogens (see here) Calcitriol (a form of Vitamin D) GnRH agonists/antagonists (see here) Gonadotropins//Antigonadotropins (see here) Plasma proteins (SHBG, ABP, Albumin) Progestogens/Antiprogestins (see here) Prolactin

Procedures	Adrenalectomy Hypophysectomy Oophorectomy Orchiectomy

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Quinestrol

See also

References