Dienestrol

Dienestrol
Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	G03CB01 (WHO) G03CC02 (WHO)
Pharmacokinetic data
Protein binding	50 to 80%
Identifiers
IUPAC name 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol
CAS Number	13029-44-2^N
PubChem (CID)	667476
IUPHAR/BPS	7160
DrugBank	DB00890^Y
ChemSpider	580857^Y
UNII	RRW32X4U1F^Y
KEGG	D00898^Y
ChEBI	CHEBI:4518^N
ChEMBL	CHEMBL1018^Y
ECHA InfoCard	100.001.381
Chemical and physical data
Formula	C₁₈H₁₈O₂
Molar mass	266.334 g/mol
3D model (Jmol)	Interactive image
SMILES Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
InChI InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+^Y Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N^Y
^NY (what is this?) (verify)

Dienestrol (INN, USAN) (brand names Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol, numerous others), also known as dienoestrol (BAN), is a synthetic, non-steroidal estrogen of the stilbestrol group used to treat menopausal symptoms in the United States and Europe.^[1]^[2]^[3]^[4] It was introduced in the U.S. in 1947 by Schering as Synestrol and in France in 1948 as Cycladiene.^[4] Dienestrol is a close analogue of diethylstilbestrol.^[5] It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively.^[6]

Dienestrol diacetate (brand names Faragynol, Gynocyrol, others) also exists and is used medically.^[2]

References

↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–. ISBN 978-3-88763-075-1.
1 2 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 390–. ISBN 978-1-4757-2085-3.
↑ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 361–. ISBN 978-3-7692-2114-5.
1 2 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–. ISBN 978-0-8155-1856-3.
↑ VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
↑ Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA (1997). "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology. 138 (3): 863–70. doi:10.1210/endo.138.3.4979. PMID 9048584.

Estrogens and antiestrogens

Estrogens

ER agonists	Steroidal: Alfatradiol Certain androgenic-anabolic steroids (e.g., testosterone, testosterone esters, nandrolone, methyltestosterone, metandienone) (via estrogenic metabolites) Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone) Clomestrone Cloxestradiol acetate Conjugated equine estrogens/esterified estrogens (Premarin) 8,9-Dehydroestrone sulfate 17α-Dihydroequilenin sulfate 17α-Dihydroequilin sulfate 17β-Dihydroequilenin sulfate 17β-Dihydroequilin sulfate Equilenin sulfate Equilin sulfate Emmenin Epiestriol Epimestrol Estetrol^† Estradiol Estradiol acetate Estradiol benzoate Estradiol butyrylacetate Estradiol cypionate^# 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 palmitate Estradiol phenylpropionate Estradiol pivalate (trimethyl estradiol acetate) Estradiol propoxyphenylpropionate Estradiol stearate Estradiol sulfate Estradiol undecylate Estradiol valerate Polyestradiol phosphate Estramustine Estriol Estriol diacetate benzoate Estriol glucuronide Estriol succinate Estriol sulfate Estriol sulfate glucuronide Estriol tripropionate Estrone Estrone acetate Estrone glucuronide Estrone sulfate Estropipate (piperazine estrone sulfate) Estrone tetraacetylglucoside Ethinyl estradiol^# Ethinyl estradiol sulfonate Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Progynon Promestriene Quinestradol Quinestrol Non-steroidal: Benzestrol Bifluranol Chlorotrianisene Dienestrol Dienestrol diacetate Diethylstilbestrol (stilbestrol) Diethylstilbestrol diacetate Diethylstilbestrol dilaurate Diethylstilbestrol dipalmitate (stilpalmitate) Diethylstilbestrol dipropionate Diethylstilbestrol disulfate Diethylstilbestrol monobenzyl ether Dimestrol (diethylstilbestrol dimethyl ether) Fosfestrol (diethylstilbestrol diphosphate) Mestilbol (diethylstilbestrol monomethyl ether) Doisynoestrol (fenocycline) Hexestrol Hexestrol diacetate Hexestrol dicaprylate Hexestrol diphosphate Hexestrol dipropionate Methallenestril Methestrol dipropionate (promethestrol dipropionate) Paroxypropione Quadrosilan Zeranol

Progonadotropins	Antiandrogens (e.g., bicalutamide) GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin) Gonadotropins (e.g., FSH, LH)

Antiestrogens

ER antagonists (incl. SERMs/SERDs)	Acolbifene^† Anordrin Bazedoxifene (+conjugated equine estrogens) Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Etacstil ^§ Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Fulvestrant

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

Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone, oxandrolone, fluoxymesterone) D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride) GnRH agonists (e.g., leuprorelin, goserelin) GnRH antagonists (e.g., cetrorelix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)

Others	Mixed mechanism of action: Danazol Gestrinone

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

See also: Androgens and antiandrogens • Progestogens and antiprogestogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH

Estrogen receptor modulators

Agonists	Steroidal: 3α-Androstanediol 3β-Androstanediol 3α-Hydroxytibolone 3β-Hydroxytibolone 4-Androstenediol 4-Androstenedione 4-Hydroxyestradiol 4-Hydroxyestrone 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, 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)	2-Hydroxyestradiol 2-Hydroxyestrone 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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