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Dienestrol diacetate

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Dienestrol diacetate
Clinical data
Trade namesFaragynol, Gynocyrol
Other namesDienestrol acetate; Lipamone
Drug classNonsteroidal estrogen;Estrogen ester
Identifiers
  • [4-[(2Z,4E)-4-(4-acetyloxyphenyl)hexa-2,4-dien-3-yl]phenyl] acetate
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H22O4
Molar mass350.414g·mol−1
3D model (JSmol)
  • C\C=C(c1ccc(OC(C)=O)cc1)/C(=C/C)c2ccc(OC(C)=O)cc2
  • InChI=1S/C22H22O4/c1-5-21(17-7-11-19(12-8-17)25-15(3)23)22(6-2)18-9-13-20(14-10-18)26-16(4)24/h5-14H,1-4H3/b21-5-,22-6+
  • Key:YWLLGDVBTLPARJ-LWKKFVLGSA-N

Dienestrol diacetate(brand namesFaragynol,Gynocyrol,others) is asyntheticnonsteroidal estrogenof thestilbestrolgroup related todiethylstilbestrol.[1]It is anesterofdienestrol.[1]

Potencies of oral estrogens[data sources 1]
Compound Dosage for specific uses (mg usually)[a]
ETD[b] EPD[b] MSD[b] MSD[c] OID[c] TSD[c]
Estradiol (non-micronized) 30 ≥120–300 120 6 - -
Estradiol (micronized) 6–12 60–80 14–42 1–2 >5 >8
Estradiol valerate 6–12 60–80 14–42 1–2 - >8
Estradiol benzoate - 60–140 - - - -
Estriol ≥20 120–150[d] 28–126 1–6 >5 -
Estriol succinate - 140–150[d] 28–126 2–6 - -
Estrone sulfate 12 60 42 2 - -
Conjugated estrogens 5–12 60–80 8.4–25 0.625–1.25 >3.75 7.5
Ethinylestradiol 200 μg 1–2 280 μg 20–40 μg 100 μg 100 μg
Mestranol 300 μg 1.5–3.0 300–600 μg 25–30 μg >80 μg -
Quinestrol 300 μg 2–4 500 μg 25–50 μg - -
Methylestradiol - 2 - - - -
Diethylstilbestrol 2.5 20–30 11 0.5–2.0 >5 3
DES dipropionate - 15–30 - - - -
Dienestrol 5 30–40 42 0.5–4.0 - -
Dienestrol diacetate 3–5 30–60 - - - -
Hexestrol - 70–110 - - - -
Chlorotrianisene - >100 - - >48 -
Methallenestril - 400 - - - -
Sources and footnotes:
  1. ^Dosages are given in milligrams unless otherwise noted.
  2. ^abcDosed every 2 to 3 weeks
  3. ^abcDosed daily
  4. ^abIn divided doses, 3x/day; irregular and atypical proliferation.
Parenteral potencies and durations of nonsteroidal estrogens
Estrogen Form Major brand name(s) EPD(14 days) Duration
Diethylstilbestrol(DES) Oil solution Metestrol 20 mg 1 mg ≈ 2–3 days; 3 mg ≈ 3 days
Diethylstilbestrol dipropionate Oil solution Cyren B 12.5–15 mg 2.5 mg ≈ 5 days
Aqueous suspension ? 5 mg ?mg = 21–28 days
Dimestrol (DESdimethyl ether) Oil solution Depot-Cyren, Depot-Oestromon, Retalon Retard 20–40 mg ?
Fosfestrol (DESdiphosphate)a Aqueous solution Honvan ? <1 day
Dienestrol diacetate Aqueous suspension Farmacyrol-Kristallsuspension 50 mg ?
Hexestrol dipropionate Oil solution Hormoestrol, Retalon Oleosum 25 mg ?
Hexestrol diphosphatea Aqueous solution Cytostesin, Pharmestrin, Retalon Aquosum ? Very short
Note:All byintramuscular injectionunless otherwise noted.Footnotes:a= Byintravenous injection.Sources:See template.

See also

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References

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  2. ^Lauritzen C (September 1990). "Clinical use of oestrogens and progestogens".Maturitas.12(3): 199–214.doi:10.1016/0378-5122(90)90004-P.PMID2215269.
  3. ^Lauritzen C (June 1977). "[Estrogen thearpy in practice. 3. Estrogen preparations and combination preparations]" [Estrogen therapy in practice. 3. Estrogen preparations and combination preparations].Fortschritte Der Medizin(in German).95(21): 1388–92.PMID559617.
  4. ^Wolf AS, Schneider HP (12 March 2013).Östrogene in Diagnostik und Therapie.Springer-Verlag. pp. 78–.ISBN978-3-642-75101-1.
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  6. ^Knörr K, Beller FK, Lauritzen C (17 April 2013).Lehrbuch der Gynäkologie.Springer-Verlag. pp. 212–213.ISBN978-3-662-00942-0.
  7. ^Horský J, Presl J (1981)."Hormonal Treatment of Disorders of the Menstrual Cycle".In Horsky J, Presl J (eds.).Ovarian Function and its Disorders: Diagnosis and Therapy.Springer Science & Business Media. pp. 309–332.doi:10.1007/978-94-009-8195-9_11.ISBN978-94-009-8195-9.
  8. ^Pschyrembel W (1968).Praktische Gynäkologie: für Studierende und Ärzte.Walter de Gruyter. pp. 598–599.ISBN978-3-11-150424-7.
  9. ^Lauritzen CH (January 1976). "The female climacteric syndrome: significance, problems, treatment".Acta Obstetricia Et Gynecologica Scandinavica. Supplement.51:47–61.doi:10.3109/00016347509156433.PMID779393.
  10. ^Lauritzen C (1975). "The Female Climacteric Syndrome: Significance, Problems, Treatment".Acta Obstetricia et Gynecologica Scandinavica.54(s51): 48–61.doi:10.3109/00016347509156433.ISSN0001-6349.
  11. ^Kopera H (1991). "Hormone der Gonaden".Hormonelle Therapie für die Frau.Kliniktaschenbücher. pp. 59–124.doi:10.1007/978-3-642-95670-6_6.ISBN978-3-540-54554-5.ISSN0172-777X.
  12. ^Scott WW, Menon M, Walsh PC (April 1980). "Hormonal Therapy of Prostatic Cancer".Cancer.45(Suppl 7): 1929–1936.doi:10.1002/cncr.1980.45.s7.1929.PMID29603164.
  13. ^Leinung MC, Feustel PJ, Joseph J (2018)."Hormonal Treatment of Transgender Women with Oral Estradiol".Transgender Health.3(1): 74–81.doi:10.1089/trgh.2017.0035.PMC5944393.PMID29756046.
  14. ^Ryden AB (1950). "Natural and synthetic oestrogenic substances; their relative effectiveness when administered orally".Acta Endocrinologica.4(2): 121–39.doi:10.1530/acta.0.0040121.PMID15432047.
  15. ^Ryden AB (1951). "The effectiveness of natural and synthetic oestrogenic substances in women".Acta Endocrinologica.8(2): 175–91.doi:10.1530/acta.0.0080175.PMID14902290.
  16. ^Kottmeier HL (1947). "Ueber blutungen in der menopause: Speziell der klinischen bedeutung eines endometriums mit zeichen hormonaler beeinflussung: Part I".Acta Obstetricia et Gynecologica Scandinavica.27(s6): 1–121.doi:10.3109/00016344709154486.ISSN0001-6349.There is no doubt that the conversion of the endometrium with injections of both synthetic and native estrogenic hormone preparations succeeds, but the opinion whether native, orally administered preparations can produce a proliferation mucosa changes with different authors. PEDERSEN-BJERGAARD (1939) was able to show that 90% of the folliculin taken up in the blood of the vena portae is inactivated in the liver. Neither KAUFMANN (1933, 1935), RAUSCHER (1939, 1942) nor HERRNBERGER (1941) succeeded in bringing a castration endometrium into proliferation using large doses of orally administered preparations of estrone or estradiol. Other results are reported by NEUSTAEDTER (1939), LAUTERWEIN (1940) and FERIN (1941); they succeeded in converting an atrophic castration endometrium into an unambiguous proliferation mucosa with 120–300 oestradiol or with 380 oestrone.
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  20. ^Duncan CJ, Kistner RW, Mansell H (October 1956)."Suppression of ovulation by trip-anisyl chloroethylene (TACE)".Obstetrics and Gynecology.8(4): 399–407.PMID13370006.