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Estropipate

Estropipate
Estropipate.png
Estropipate molecule ball.png
Clinical data
Trade namesHarmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others
Other namesPiperazine estrone sulfate; Estrone sulfate piperazine salt; Pipestrone
AHFS/Drugs.comMonograph
Routes of
administration
By mouth
Drug classEstrogen; Estrogen ester
ATC code
  • None
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.027.906 Edit this at Wikidata
Chemical and physical data
FormulaC22H32N2O5S
Molar mass436.56 g/mol g·mol−1
3D model (JSmol)
  (verify)

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

Estropipate is used to:[1][additional citation(s) needed]

Estrogen dosages for menopausal hormone therapy

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 5–15 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

Estropipate is available in the form of 0.75, 1.5, 3, and 6 mg oral tablets.[5]

Pharmacology

Pharmacodynamics

Estropipate is a prodrug of estrone and estradiol. Hence, it is an estrogen, or an agonist of the estrogen receptors.

Estropipate has been found to act as an inhibitor of SLCO1B1 (OATP1B1) (IC50 = 70 nM).[6]

Relative oral potencies of estrogens

Estrogen Type HF VE UCa FSH LH HDL-C SHBG CBG AGT Liver
Estradiol Bioidentical 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0
Estrone Bioidentical ? ? ? 0.3 0.3 ? ? ? ? ?
Estriol Bioidentical 0.3 0.3 0.1 0.3 0.3 0.2 ? ? ? 0.67
Estrone sulfate Bioidentical ? 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 Natural 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 Natural ? ? 1.0 ? ? 6.0 7.5 6.0 7.5 ?
Ethinylestradiol Synthetic 120 150 400 60–150 100 400 500–600 500–600 350 2.9–5.0
Diethylstilbestrol Synthetic ? ? ? 2.9–3.4 ? ? 26–28 25–37 20 5.7–7.5
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 (specifically hot flashes relief and gonadotropin suppression). Type: Bioidentical = Identical to those found in humans. Natural = Naturally occurring but not identical to those found in humans (e.g., estrogens of other species). Synthetic = Man-made, does not occur naturally in animals or in the environment. Sources: See template.

Pharmacokinetics

Estropipate is hydrolyzed into estrone in the body.[7] Estrone can then be transformed into estradiol by 17β-hydroxysteroid dehydrogenase.

Chemistry

History

Estropipate was introduced for medical use by Abbott in 1968.[8] It was approved by the FDA in the United States in 1991.[9]

Society and culture

Generic names

Estropipate is the generic name of the drug and its INN, USAN, and BAN.[2][3][10][7][11]

Brand names

Estropipate is or has been marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.[11][2][10][7]

Availability

Estropipate appears to remain available only in the United States.[11] In the past, estropipate has also been marketed in Canada, the United Kingdom, Ireland, Switzerland, Australia, South Africa, Mexico, and Indonesia.[11][10][7]

References

  1. ^ a b c [www.accessdata.fda.gov]
  2. ^ a b c d J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 900–. ISBN 978-1-4757-2085-3.
  3. ^ a b c I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 114–. ISBN 978-94-011-4439-1.
  4. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1484–. ISBN 978-0-8155-1856-3.
  5. ^ Joseph T. DiPiro; Robert L. Talbert; Gary C. Yee; Gary R. Matzke, Barbara G. Wells, L. Michael Posey (23 January 2017). Pharmacotherapy: A Pathophysiologic Approach, Tenth Edition. McGraw-Hill Education. p. 1295. ISBN 978-1-259-58749-8.CS1 maint: multiple names: authors list (link)
  6. ^ [www.fasebj.org]
  7. ^ a b c d Sweetman, Sean C., 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.
  8. ^ Penny Wise Budoff (1 August 1983). No more hot flashes, and other good news. Putnam. p. 28. ISBN 978-0-399-12793-9.
  9. ^ P & T. CORE Medical Journals. July 1993.
  10. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1.
  11. ^ a b c d [www.drugs.com]