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(Top) 1 Isomers 2 See also 3 Notes 4 References

Dienestrol

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Dienestrol
Clinical data

Trade names	Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Cycladiene, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol
Other names	Dienoestrol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol; 3,4-Di(para-hydroxyphenyl)-2,4-hexadiene
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Drug class	Nonsteroidal estrogen
ATC code	G03CB01 (WHO) G03CC02 (WHO)
Identifiers
IUPAC name 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
CAS Number	13029-44-2^N
PubChem CID	667476
IUPHAR/BPS	7160
DrugBank	DB00890^Y
ChemSpider	580857^Y
UNII	RRW32X4U1F
KEGG	D00898^Y
ChEBI	CHEBI:4518^N
ChEMBL	ChEMBL1018^Y
CompTox Dashboard (EPA)	DTXSID7022382
ECHA InfoCard	100.001.381
Chemical and physical data
Formula	C₁₈H₁₈O₂
Molar mass	266.340 g·mol⁻¹
3D model (JSmol)	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 (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (brand names Dienoestrol, Denestrolin, Dienol and many others^[a]), also known as dienoestrol (BANTooltip British Approved Name), is a synthetic nonsteroidal estrogen medication of the stilbestrol group which is or was used to treat menopausal symptoms in the United States and Europe.^[1]^[2]^[3]^[4] It has been studied for use by rectal administration in the treatment of prostate cancer in men as well.^[5] The medication was introduced in the U.S. in 1947 by ScheringasSynestrol and in France in 1948 as Cycladiene.^[4] Dienestrol is a close analogueofdiethylstilbestrol.^[6] It has approximately 223% and 404% of the affinityofestradiol at the ERα and ERβ, respectively.^[7]

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

Isomers[edit]

Dienestrol (unspecified) - CAS 84-17-3
E,E-Dienestrol - CAS 13029-44-2
Z,Z-Dienestrol - CAS 35495-11-5

Notes[edit]

^ Other trade names of the medication include Ortho Dienestrol, Dienoestrol Ortho, Sexadien, Dinovex, Follormon, Oestrodiene, and Synestrol

References[edit]

^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–. ISBN 978-3-88763-075-1.

^ ^a ^b 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.

^ ^a ^b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–. ISBN 978-0-8155-1856-3.

^ Sambuelli M (1953). "Somministrazione degli estrogeni per via rettale nel carcinoma prostatico" [Rectal administration of estrogens in prostate carcinoma]. Minerva Urol (in Italian). 5 (1): 28–32. ISSN 0026-4989. PMID 13063334.

^ 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 androgens/anabolic steroids (e.g., testosterone, testosterone esters, methyltestosterone, metandienone, nandrolone esters) (via estrogenic metabolites)
Certain progestins (e.g., norethisterone, noretynodrel, etynodiol diacetate, tibolone)
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
Esterified estrogens
Estetrol^†
Estradiol
Estradiol esters (e.g., estradiol acetate, estradiol benzoate, estradiol cypionate, estradiol enanthate, estradiol undecylate, estradiol valerate, polyestradiol phosphate, estradiol ester mixtures (Climacteron))
Estramustine phosphate
Estriol
Estriol esters (e.g., estriol succinate, polyestriol phosphate)
Estrogenic substances
Estrone
Estrone esters
- Estrone sulfate
- Estropipate (piperazine estrone sulfate)
Ethinylestradiol^#
- Ethinylestradiol sulfonate
Hydroxyestrone diacetate
Mestranol
Methylestradiol
Moxestrol
Nilestriol
Prasterone (dehydroepiandrosterone; DHEA)
- Prasterone enanthate
- Prasterone sulfate
Promestriene
Quinestradol
Quinestrol

Progonadotropins

Antiandrogens (e.g., bicalutamide)
GnRH agonists (e.g., GnRH (gonadorelin), leuprorelin)
Gonadotropins (e.g., FSHTooltip follicle-stimulating hormone, LHTooltip luteinizing hormone)

Antiestrogens

ERTooltip Estrogen receptor antagonists (incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene^† Anordrin Bazedoxifene Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Elacestrant Fulvestrant Noncompetitive inhibitors: Trilostane
Aromatase inhibitors	First-generation: Aminoglutethimide Testolactone Second-generation: Fadrozole Formestane Third-generation: Anastrozole Exemestane Letrozole
Antigonadotropins	Androgens/anabolic steroids (e.g., testosterone, testosterone esters, nandrolone esters, 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, elagolix) Progestogens (e.g., chlormadinone acetate, cyproterone acetate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone acetate, megestrol acetate)
Others	Mixed mechanism of action: Danazol Gestrinone Androstenedione immunogens: Androvax (androstenedione albumin) Ovandrotone albumin (Fecundin)