{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(3''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-17-ethynyl-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[''a'']phenanthren-3-yl] 3-cyclohexylpropanoate | image = Ethandrostate.svg | image_class = skin-invert-image | width =
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth, intramuscular injection | class = Estrogen
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = | CAS_number = | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 227055 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 197507 | UNII = | KEGG = | ChEBI = | ChEMBL = | synonyms = Ethynylandrostenediol 3β-cyclohexanepropionate; 17α-Ethynylandrost-5-ene-3β,17β-diol 3β-cyclohexanepropionate; 17α-Pregn-5-en-20-yne-3β,17β-diol 3β-cyclohexanepropionate; NSC-18216
<!--Chemical data--> | C=30 | H=44 | O=3 | SMILES = C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)OC(=O)CCC5CCCCC5 | StdInChI_Ref = | StdInChI = 1S/C30H44O3/c1-4-30(32)19-16-26-24-12-11-22-20-23(33-27(31)13-10-21-8-6-5-7-9-21)14-17-28(22,2)25(24)15-18-29(26,30)3/h1,11,21,23-26,32H,5-10,12-20H2,2-3H3/t23-,24+,25-,26-,28-,29-,30-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = VGTIQIQOBZXZAI-IODDZSIWSA-N }}
'''Ethandrostate''', also known as '''ethinylandrostenediol 3β-cyclohexanepropionate''', is a synthetic steroidal estrogen and ester of ethinylandrostenediol (17α-ethynyl-5-androstenediol) which was developed and studied in people with certain cancers like breast cancer and prostate cancer in the 1950s but was never marketed.<ref name="Shipley1962">{{cite book|author=Elva G. Shipley|chapter=Anti-gonadotropic steroids, inhibition of ovulation and mating|pages=179–274| veditors = Dorfman RI |title=Bioassay|chapter-url=https://books.google.com/books?id=WS_LBAAAQBAJ&pg=PA179|date=1962|publisher=Elsevier|isbn=978-1-4832-7276-4}}</ref><ref name="BoccabellaBakritges1956">{{cite journal | vauthors = Boccabella A, Bakritges C | title = Effects of ethandrostate on pituitary and sex organs of rats | journal = Anatomical Record | date = January 1956 | volume = 124 | issue = 2 | pages = 260 }}</ref><ref name="ClintonNeumann1957">{{cite journal| vauthors = Clinton R, Neumann H, Laskowski S, Christiansen R |title=Notes - Esters of 17α-Ethinyl-androstane-3β,17β-diol and 17 α-Ethinylandrost-5-ene-3β, 17β-diol|journal=The Journal of Organic Chemistry|volume=22|issue=4|year=1957|pages=473–475|issn=0022-3263|doi=10.1021/jo01355a627}}</ref><ref name="pmid13523561">{{cite journal | vauthors = Olson KB, Frawley TF, Stein AA, Shields D | title = Ethandrostate: endocrine effects and studies in treatment of cancer | journal = Cancer | volume = 11 | issue = 3 | pages = 537–45 | date = 1958 | pmid = 13523561 | doi = 10.1002/1097-0142(195805/06)11:3<537::aid-cncr2820110313>3.0.co;2-w | s2cid = 738607 | doi-access = }}</ref> Although far less potent by weight than estradiol or estrone, ethandrostate produces estrogenic effects in the vagina, uterus, and mammary glands as well as antigonadotropic and secondary antiandrogenic effects like testicular and prostate atrophy in both animals and humans.<ref name="Shipley1962" /><ref name="ClintonNeumann1957" /><ref name="pmid13523561" /> Ethandrostate was assessed in humans as an aqueous suspension by intramuscular injection at doses of 100 to 200 mg/day or 100 mg three times per week and by mouth at a dose of 25 mg four times per day.<ref name="pmid13523561" /> It shows much greater antigonadotropic potency relative to general estrogenic potency in animals when compared with other estrogens.<ref name="ClintonNeumann1957" /> However, this doesn't seem to be the case in humans.<ref name="pmid13523561" /> In addition to its estrogenic activity, ethandrostate has very weak androgenic activity that manifests only at doses much higher than its estrogenic activity.<ref name="ClintonNeumann1957" />
{{Affinities of estrogen receptor ligands for the ERα and ERβ}}
==References== {{Reflist}}
{{Androgen receptor modulators}} {{Estrogen receptor modulators}} {{Progesterone receptor modulators}}
Category:Abandoned drugs Category:Ethynyl compounds Category:Androgens Category:Androstanes Category:Antigonadotropins Category:Diols Category:Esters Category:Experimental cancer drugs Category:Progestogens Category:Synthetic estrogens
{{Androgen-stub}} {{Genito-urinary-drug-stub}} {{Antineoplastic-drug-stub}}