Estropipate
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Clinical data | |
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Trade names | Harmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others |
Other names | Piperazine estrone sulfate; Estrone sulfate piperazine salt; Pipestrone |
AHFS/Drugs.com | Monograph |
Routes of administration | By mouth |
Drug class | Estrogen; Estrogen ester |
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ECHA InfoCard | 100.027.906 |
Chemical and physical data | |
Formula | C22H32N2O5S |
Molar mass | 436.57 g·mol−1 |
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Estropipate, also known as piperazine estrone sulfate and sold under the brand names Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatment of menopausal symptoms.[1][2][3][4] It is a salt of estrone sulfate and piperazine, and is transformed into estrone and estradiol in the body.[2][3] It is taken by mouth.[1]
Medical uses[edit]
Estropipate is used to:[1][additional citation(s) needed]
- Alleviate symptoms of menopause as menopausal hormone therapy
- Treat some types of infertility
- Treat some conditions leading to underdevelopment of female sexual characteristics
- Treat vaginal atrophy
- Treat some types of breast cancer (particularly in men and postmenopausal women)
- Treat prostate cancer
- Prevent osteoporosis
Route/form | Estrogen | Low | Standard | High | |||
---|---|---|---|---|---|---|---|
Oral | Estradiol | 0.5–1 mg/day | 1–2 mg/day | 2–4 mg/day | |||
Estradiol valerate | 0.5–1 mg/day | 1–2 mg/day | 2–4 mg/day | ||||
Estradiol acetate | 0.45–0.9 mg/day | 0.9–1.8 mg/day | 1.8–3.6 mg/day | ||||
Conjugated estrogens | 0.3–0.45 mg/day | 0.625 mg/day | 0.9–1.25 mg/day | ||||
Esterified estrogens | 0.3–0.45 mg/day | 0.625 mg/day | 0.9–1.25 mg/day | ||||
Estropipate | 0.75 mg/day | 1.5 mg/day | 3 mg/day | ||||
Estriol | 1–2 mg/day | 2–4 mg/day | 4–8 mg/day | ||||
Ethinylestradiola | 2.5–10 μg/day | 5–20 μg/day | – | ||||
Nasal spray | Estradiol | 150 μg/day | 300 μg/day | 600 μg/day | |||
Transdermal patch | Estradiol | 25 μg/dayb | 50 μg/dayb | 100 μg/dayb | |||
Transdermal gel | Estradiol | 0.5 mg/day | 1–1.5 mg/day | 2–3 mg/day | |||
Vaginal | Estradiol | 25 μg/day | – | – | |||
Estriol | 30 μg/day | 0.5 mg 2x/week | 0.5 mg/day | ||||
IM or SC injection | Estradiol valerate | – | – | 4 mg 1x/4 weeks | |||
Estradiol cypionate | 1 mg 1x/3–4 weeks | 3 mg 1x/3–4 weeks | 5 mg 1x/3–4 weeks | ||||
Estradiol benzoate | 0.5 mg 1x/week | 1 mg 1x/week | 1.5 mg 1x/week | ||||
SC implant | Estradiol | 25 mg 1x/6 months | 50 mg 1x/6 months | 100 mg 1x/6 months | |||
Footnotes: a = No longer used or recommended, due to health concerns. b = As a single patch applied once or twice per week (worn for 3–4 days or 7 days), depending on the formulation. Note: Dosages are not necessarily equivalent. Sources: See template. |
Available forms[edit]
Estropipate is available in the form of 0.75, 1.5, 3, and 6 mg oral tablets.[5]
Pharmacology[edit]
Pharmacodynamics[edit]
Estropipate is a prodrug of estrone and estradiol. Hence, it is an estrogen, or an agonist of the estrogen receptors.
Estrogen | HF | VE | UCa | FSH | LH | HDL-C | SHBG | CBG | AGT | Liver |
---|---|---|---|---|---|---|---|---|---|---|
Estradiol | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 |
Estrone | ? | ? | ? | 0.3 | 0.3 | ? | ? | ? | ? | ? |
Estriol | 0.3 | 0.3 | 0.1 | 0.3 | 0.3 | 0.2 | ? | ? | ? | 0.67 |
Estrone sulfate | ? | 0.9 | 0.9 | 0.8–0.9 | 0.9 | 0.5 | 0.9 | 0.5–0.7 | 1.4–1.5 | 0.56–1.7 |
Conjugated estrogens | 1.2 | 1.5 | 2.0 | 1.1–1.3 | 1.0 | 1.5 | 3.0–3.2 | 1.3–1.5 | 5.0 | 1.3–4.5 |
Equilin sulfate | ? | ? | 1.0 | ? | ? | 6.0 | 7.5 | 6.0 | 7.5 | ? |
Ethinylestradiol | 120 | 150 | 400 | 60–150 | 100 | 400 | 500–600 | 500–600 | 350 | 2.9–5.0 |
Diethylstilbestrol | ? | ? | ? | 2.9–3.4 | ? | ? | 26–28 | 25–37 | 20 | 5.7–7.5 |
Sources and footnotes
Notes: Values are ratios, with estradiol as standard (i.e., 1.0). Abbreviations: HF = Clinical relief of hot flashes. VE = Increased proliferation of vaginal epithelium. UCa = Decrease in UCa. FSH = Suppression of FSH levels. LH = Suppression of LH levels. HDL-C, SHBG, CBG, and AGT = Increase in the serum levels of these liver proteins. Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (hot flashes/gonadotropins). Sources: See template. |
Pharmacokinetics[edit]
Estropipate is hydrolyzed into estrone in the body.[6] Estrone can then be transformed into estradiol by 17β-hydroxysteroid dehydrogenase.
Chemistry[edit]
History[edit]
Estropipate was introduced for medical use by Abbott in 1968.[7] It was approved by the FDA in the United States in 1991.[8]
Society and culture[edit]
Generic names[edit]
Estropipate is the generic name of the drug and its INN, USAN, and BAN.[2][3][9][6][10]
Brand names[edit]
Estropipate is or has been marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.[10][2][9][6]
Availability[edit]
Estropipate appears to remain available only in the United States.[10] In the past, estropipate has also been marketed in Canada, the United Kingdom, Ireland, Switzerland, Australia, South Africa, Mexico, and Indonesia.[10][9][6]
References[edit]
- ^ a b c "Ogen, estropipate tablets, USP" (PDF). Pharmacia & Upjohn Co. U.S. Food and Drug Administration. December 2004.
- ^ a b c d Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 900–. ISBN 978-1-4757-2085-3.
- ^ a b c Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 114–. ISBN 978-94-011-4439-1.
- ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1484–. ISBN 978-0-8155-1856-3.
- ^ DiPiro JT, Talbert RL, Yee GC, Matzke GR, Wells BG, Posey ML (23 January 2017). Pharmacotherapy: A Pathophysiologic Approach, Tenth Edition. McGraw-Hill Education. p. 1295. ISBN 978-1-259-58749-8.
- ^ a b c d Sweetman SC, ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2101. ISBN 978-0-85369-840-1.
- ^ Budoff PW (1 August 1983). No more hot flashes, and other good news. Putnam. p. 28. ISBN 978-0-399-12793-9.
- ^ P & T. CORE Medical Journals. July 1993.
- ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1.
- ^ a b c d "Estropipate". Drugs.com.