Dienestrol
Clinical data | |
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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 | |
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ECHA InfoCard | 100.001.381 |
Chemical and physical data | |
Formula | C18H18O2 |
Molar mass | 266.334 g/mol g·mol−1 |
3D model (JSmol) | |
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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 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]
Route/form | Estrogen | Dosage | Ref(s) |
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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] | |
IM 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. |
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 | |
IM 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
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- ^ 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.
- ^ 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.
- ^ "ESTRACE® TABLETS (estradiol tablets, USP) FDA label" (PDF). 2005.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Premarin® (conjugated estrogens tablets, USP) FDA label" (PDF). 2003.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Estradurin® (polyestradiol phosphate) information and labels". Pharmanovia.
- ^ 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.
- ^ "Estrone suspension FDA review" (PDF). 1979.