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'''Dienestrol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}) (brand names '''Ortho Dienestrol''', '''Dienoestrol''', '''Dienoestrol Ortho''', '''Sexadien''', '''Denestrolin''', '''Dienol''', '''Dinovex''', '''Follormon''', '''Oestrodiene''', '''Synestrol''', numerous others), also known as '''dienoestrol''' ({{abbrlink|BAN|British Approved Name}}), is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] of the [[stilbestrol]] group which is or was used to treat [[menopause|menopausal]] symptoms in the [[United States]] and [[Europe]].<ref>{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA331|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=331–}}</ref><ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA390|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=390–}}</ref><ref name="Muller1998">{{cite book|author=Muller|title=European Drug Index: European Drug Registrations, Fourth Edition|url=https://books.google.com/books?id=2HBPHmclMWIC&pg=PA361|date=19 June 1998|publisher=CRC Press|isbn=978-3-7692-2114-5|pages=361–}}</ref><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1286|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1286–}}</ref> It has been studied for use by [[rectal administration]] in the treatment of [[prostate cancer]] in men as well.<ref name="pmid13063334">{{cite journal | vauthors = Sambuelli M | title = Somministrazione degli estrogeni per via rettale nel carcinoma prostatico. | trans-title = Rectal administration of estrogens in prostate carcinoma | language = Italian | journal = Minerva Urol | volume = 5 | issue = 1 | pages = 28–32 | date = 1953 | issn = 0026-4989 | pmid = 13063334 | doi = | url = }}</ref> The medication was introduced in the U.S. in 1947 by [[Schering AG|Schering]] as '''Synestrol''' and in France in 1948 as '''Cycladiene'''.<ref name="Publishing2013" /> Dienestrol is a close [[structural analog|analogue]] of [[diethylstilbestrol]].<ref>{{cite book|title=VITAMINS AND HORMONES|url=https://archive.org/details/in.ernet.dli.2015.5563|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=[https://archive.org/details/in.ernet.dli.2015.5563/page/n253 233]–}}</ref> It has approximately 223% and 404% of the [[affinity (pharmacology)|affinity]] of [[estradiol]] at the [[ERα]] and [[ERβ]], respectively.<ref name="pmid9048584">{{cite journal | vauthors = Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA | title = Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta | journal = Endocrinology | volume = 138 | issue = 3 | pages = 863–70 | year = 1997 | pmid = 9048584 | doi = 10.1210/endo.138.3.4979 | url = }}</ref>
'''Dienestrol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}) (brand names '''Ortho Dienestrol''', '''Dienoestrol''', '''Dienoestrol Ortho''', '''Sexadien''', '''Denestrolin''', '''Dienol''', '''Dinovex''', '''Follormon''', '''Oestrodiene''', '''Synestrol''', numerous others), also known as '''dienoestrol''' ({{abbrlink|BAN|British Approved Name}}), is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] of the [[stilbestrol]] group which is or was used to treat [[menopause|menopausal]] symptoms in the [[United States]] and [[Europe]].<ref>{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA331|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=331–}}</ref><ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA390|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=390–}}</ref><ref name="Muller1998">{{cite book|author=Muller|title=European Drug Index: European Drug Registrations, Fourth Edition|url=https://books.google.com/books?id=2HBPHmclMWIC&pg=PA361|date=19 June 1998|publisher=CRC Press|isbn=978-3-7692-2114-5|pages=361–}}</ref><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia, 3rd Edition|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1286|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1286–}}</ref> It has been studied for use by [[rectal administration]] in the treatment of [[prostate cancer]] in men as well.<ref name="pmid13063334">{{cite journal | vauthors = Sambuelli M | title = Somministrazione degli estrogeni per via rettale nel carcinoma prostatico. | trans-title = Rectal administration of estrogens in prostate carcinoma | language = Italian | journal = Minerva Urol | volume = 5 | issue = 1 | pages = 28–32 | date = 1953 | issn = 0026-4989 | pmid = 13063334 | doi = | url = }}</ref> The medication was introduced in the U.S. in 1947 by [[Schering AG|Schering]] as '''Synestrol''' and in France in 1948 as '''Cycladiene'''.<ref name="Publishing2013" /> Dienestrol is a close [[structural analog|analogue]] of [[diethylstilbestrol]].<ref>{{cite book|title=VITAMINS AND HORMONES|url=https://archive.org/details/in.ernet.dli.2015.5563|date=1 January 1945|publisher=Academic Press|isbn=978-0-08-086600-0|pages=[https://archive.org/details/in.ernet.dli.2015.5563/page/n253 233]–}}</ref> It has approximately 223% and 404% of the [[affinity (pharmacology)|affinity]] of [[estradiol]] at the [[ERα]] and [[ERβ]], respectively.<ref name="pmid9048584">{{cite journal | vauthors = Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA | title = Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta | journal = Endocrinology | volume = 138 | issue = 3 | pages = 863–70 | year = 1997 | pmid = 9048584 | doi = 10.1210/endo.138.3.4979 | url = | doi-access = free }}</ref>


[[Dienestrol diacetate]] (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.<ref name="Elks2014" />
[[Dienestrol diacetate]] (brand names Faragynol, Gynocyrol, others) also exists and has been used medically.<ref name="Elks2014" />

Revision as of 00:02, 13 April 2020

Dienestrol
Clinical data
Trade namesOrtho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Cycladiene, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol
Other namesDienoestrol; p-[(E,E)-1-Ethylidene-2-(p-hydroxyphenyl)-2-butenyl]phenol; 3,4-Di(para-hydroxyphenyl)-2,4-hexadiene
AHFS/Drugs.comMicromedex Detailed Consumer Information
Drug classNonsteroidal estrogen
ATC code
Identifiers
  • 4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.381 Edit this at Wikidata
Chemical and physical data
FormulaC18H18O2
Molar mass266.334 g/mol g·mol−1
3D model (JSmol)
  • Oc2ccc(C(/C(c1ccc(O)cc1)=C/C)=C\C)cc2
  • 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+ checkY
  • Key:NFDFQCUYFHCNBW-SCGPFSFSSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dienestrol (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (brand names Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol, numerous others), also known as dienoestrol (BANTooltip British Approved Name), is a synthetic nonsteroidal estrogen 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 Schering as Synestrol and in France in 1948 as Cycladiene.[4] Dienestrol is a close analogue of diethylstilbestrol.[6] It has approximately 223% and 404% of the affinity of estradiol at the ERα and ERβ, respectively.[7]

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

Estrogen dosages for breast cancer
Route/form Estrogen Dosage Ref(s)
Oral Estradiol 10 mg 3x/day
AI-resistant: 2 mg 1–3x/day		 [8][9]
[8][10]
Estradiol valerate AI-resistant: 2 mg 1–3x/day [8][10]
Conjugated estrogens 10 mg 3x/day [11][12][13][14]
Ethinylestradiol 0.5–1 mg 3x/day [12][8][15][14]
Diethylstilbestrol 5 mg 3x/day [12][16][17]
Dienestrol 5 mg 3x/day [15][14][17]
Dimestrol 30 mg/day [11][14][17]
Chlorotrianisene 24 mg/day [11][17]
IMTooltip Intramuscular or SC injection Estradiol benzoate 5 mg 2–3x/week [15][18][16][19]
Estradiol dipropionate 5 mg 2–3x/week [15][16][20][19]
Estradiol valerate 30 mg 1x/2 weeks [18]
Polyestradiol phosphate 40–80 mg 1x/4 weeks [21][22]
Estrone 5 mg ≥3x/week [23]
Notes: (1) Only in women who are at least 5 years postmenopausal.[8] (2) Dosages are not necessarily equivalent.
Estrogen dosages for prostate cancer
Route/form Estrogen Dosage
Oral Estradiol 1–2 mg 3x/day
Conjugated estrogens 1.25–2.5 mg 3x/day
Ethinylestradiol 0.15–3 mg/day
Ethinylestradiol sulfonate 1–2 mg 1x/week
Diethylstilbestrol 1–3 mg/day
Dienestrol 5 mg/day
Hexestrol 5 mg/day
Fosfestrol 100–480 mg 1–3x/day
Chlorotrianisene 12–48 mg/day
Quadrosilan 900 mg/day
Estramustine phosphate 140–1400 mg/day
Transdermal patch Estradiol 2–6x 100 μg/day
Scrotal: 1x 100 μg/day
IMTooltip Intramuscular or SC injection Estradiol benzoate 1.66 mg 3x/week
Estradiol dipropionate 5 mg 1x/week
Estradiol valerate 10–40 mg 1x/1–2 weeks
Estradiol undecylate 100 mg 1x/4 weeks
Polyestradiol phosphate Alone: 160–320 mg 1x/4 weeks
With oral EE: 40–80 mg 1x/4 weeks
Estrone 2–4 mg 2–3x/week
IV injection Fosfestrol 300–1200 mg 1–7x/week
Estramustine phosphate 240–450 mg/day
Note: Dosages are not necessarily equivalent. Sources: See template.

See also

References

  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 331–. ISBN 978-3-88763-075-1.
  2. ^ 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.
  3. ^ Muller (19 June 1998). European Drug Index: European Drug Registrations, Fourth Edition. CRC Press. pp. 361–. ISBN 978-3-7692-2114-5.
  4. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1286–. ISBN 978-0-8155-1856-3.
  5. ^ 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.
  6. ^ VITAMINS AND HORMONES. Academic Press. 1 January 1945. pp. 233–. ISBN 978-0-08-086600-0.
  7. ^ 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.
  8. ^ a b c d e Coelingh Bennink HJ, Verhoeven C, Dutman AE, Thijssen J (January 2017). "The use of high-dose estrogens for the treatment of breast cancer". Maturitas. 95: 11–23. doi:10.1016/j.maturitas.2016.10.010. PMID 27889048.
  9. ^ "ESTRACE® TABLETS (estradiol tablets, USP) FDA label" (PDF). 2005.
  10. ^ a b Palmieri C, Patten DK, Januszewski A, Zucchini G, Howell SJ (January 2014). "Breast cancer: current and future endocrine therapies". Mol. Cell. Endocrinol. 382 (1): 695–723. doi:10.1016/j.mce.2013.08.001. PMID 23933149.
  11. ^ a b c Green RB, Sethi RS, Lindner HH (July 1964). "Treatment of advanced carcinoma of the breast: Progress in therapy during the past decade". Am. J. Surg. 108: 107–21. doi:10.1016/0002-9610(64)90094-7. PMID 14182428.
  12. ^ a b c Thomas, John A.; Keenan, Edward J. (6 December 1986). "Estrogens and Antiestrogenic Drugs". Principles of Endocrine Pharmacology. Springer Science & Business Media. pp. 135–165. doi:10.1007/978-1-4684-5036-1_7. ISBN 978-1-4684-5036-1.
  13. ^ "Premarin® (conjugated estrogens tablets, USP) FDA label" (PDF). 2003.
  14. ^ a b c d Van Winkle, Walton (1949). "Council on Pharmacy and Chemistry. Estrogens and Androgens in Mammary Cancer". JAMA: The Journal of the American Medical Association. 140 (15): 1214. doi:10.1001/jama.1949.02900500022007. ISSN 0098-7484.
  15. ^ a b c d Kahr, Ernst (1966). "Die Allgemeinbehandlung" [General Treatment]. Der Inoperable Krebskranke: Möglichkeiten der Therapie in Klinik und Praxis [The Inoperable Cancer Patient: Possibilities of Therapy in Clinic and Practice]. Springer-Verlag. pp. 104–155. doi:10.1007/978-3-642-86140-6_4. ISBN 978-3-642-86140-6.
  16. ^ a b c Dao, Thomas L. (1975). "Pharmacology and Clinical Utility of Hormones in Hormone Related Neoplasms". In Alan C. Sartorelli; David G. Johns (eds.). Antineoplastic and Immunosuppressive Agents. pp. 170–192. doi:10.1007/978-3-642-65806-8_11. ISBN 978-3-642-65806-8.
  17. ^ a b c d Nathanson IT, Kelley RM (January 1952). "Hormonal treatment of cancer". N. Engl. J. Med. 246 (5): 180–9, concl. doi:10.1056/NEJM195201312460505. PMID 14890833.
  18. ^ a b Dobson L (August 1962). "The management of metastatic breast cancer". Surg. Clin. North Am. 42: 861–76. doi:10.1016/S0039-6109(16)36728-7. PMID 13886800.
  19. ^ a b Martz G (13 March 2013). Die hormonale Therapie maligner Tumoren: Endokrine Behandlungsmethoden des metastasierenden Mamma-, Prostata- und Uterus-Corpuscarcinoms. Springer-Verlag. pp. 39–. ISBN 978-3-642-86282-3.
  20. ^ Committee on Research, AMA (1960). "Androgens and estrogens in the treatment of disseminated mammary carcinoma. Retrospective study of nine hundred forty-four patients". Journal of the American Medical Association. 172 (12): 1271. doi:10.1001/jama.1960.03020120049010. ISSN 0002-9955.
  21. ^ "Estradurin® (polyestradiol phosphate) information and labels". Pharmanovia.
  22. ^ Ostrowski MJ, Jackson AW (1979). "Polyestradiol phosphate: a preliminary evaluation of its effect on breast carcinoma". Cancer Treat Rep. 63 (11–12): 1803–7. PMID 393380.
  23. ^ "Estrone suspension FDA review" (PDF). 1979.



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