Estropipate

Estropipate
Names
Trade namesHarmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others
Other namesPiperazine estrone sulfate;[1] Estrone sulfate piperazine salt; Pipestrone
IUPAC name
  • [(8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate; piperazine
Clinical data
Drug classEstrogen
Main usesMenopause, ovarian failure[1]
Side effectsHeadache, breast pain, irregular vaginal bleeding, abdominal cramps, nausea[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		By mouth
External links
AHFS/Drugs.comMonograph
Chemical and physical data
FormulaC22H32N2O5S
Molar mass436.57 g·mol−1
3D model (JSmol)
SMILES
  • O=S(=O)(O)Oc1cc4c(cc1)[C@@H]3[C@H]([C@@H]2CCC(=O)[C@@]2(C)CC3)CC4.N1CCNCC1
InChI
  • InChI=1S/C18H22O5S.C4H10N2/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19;1-2-6-4-3-5-1/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22);5-6H,1-4H2/t14-,15-,16+,18+;/m1./s1 checkY
  • Key:HZEQBCVBILBTEP-ZFINNJDLSA-N checkY

Estropipate, sold under the brand name Ogen among others, is a medication used to treat the symptoms of menopause and ovarian failure.[1] It was previously also used to prevent postmenopausal osteoporosis.[1] It is taken by mouth.[1]

Common side effects include headache, breast pain, irregular vaginal bleeding, abdominal cramps, and nausea.[1] Other side effects may include high blood pressure, liver problems, high sugar, swelling, hair loss, and vaginal yeast infections.[1] Rarely blood clots or gallbladder disease may occur.[1] It is an estrogen, specifically a salt of estrone sulfate and piperazine, which is transformed into estrone and estradiol in the body.[2][3]

Estropipate was first made commercially in the United States in 1950.[4] In the United States 100 tablets of 0.75 mg used to cost about 50 USD.[5] Production; however, has been discontinued in the United States as of 2021.[6][7]

Medical uses

Estropipate is used to:[8]

Estrogen dosages for menopausal hormone therapy
Route/formEstrogenLowStandardHigh
OralEstradiol0.5–1 mg/day1–2 mg/day2–4 mg/day
Estradiol valerate0.5–1 mg/day1–2 mg/day2–4 mg/day
Estradiol acetate0.45–0.9 mg/day0.9–1.8 mg/day1.8–3.6 mg/day
Conjugated estrogens0.3–0.45 mg/day0.625 mg/day0.9–1.25 mg/day
Esterified estrogens0.3–0.45 mg/day0.625 mg/day0.9–1.25 mg/day
Estropipate0.75 mg/day1.5 mg/day3 mg/day
Estriol1–2 mg/day2–4 mg/day4–8 mg/day
Ethinylestradiola2.5 μg/day5–15 μg/day–
Nasal sprayEstradiol150 μg/day300 μg/day600 μg/day
Transdermal patchEstradiol25 μg/dayb50 μg/dayb100 μg/dayb
Transdermal gelEstradiol0.5 mg/day1–1.5 mg/day2–3 mg/day
VaginalEstradiol25 μg/day––
Estriol30 μg/day0.5 mg 2x/week0.5 mg/day
IM or SC injectionEstradiol valerate––4 mg 1x/4 weeks
Estradiol cypionate1 mg 1x/3–4 weeks3 mg 1x/3–4 weeks5 mg 1x/3–4 weeks
Estradiol benzoate0.5 mg 1x/week1 mg 1x/week1.5 mg 1x/week
SC implantEstradiol25 mg 1x/6 months50 mg 1x/6 months100 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.[9]

Pharmacology

Pharmacodynamics

See also: Pharmacodynamics of estradiol

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

Relative oral potencies of estrogens
EstrogenHFVEUCaFSHLHHDL-CSHBGCBGAGTLiver
Estradiol1.01.01.01.01.01.01.01.01.01.0
Estrone ? ? ?0.30.3 ? ? ? ? ?
Estriol0.30.30.10.30.30.2 ? ? ?0.67
Estrone sulfate ?0.90.90.8–0.90.90.50.90.5–0.71.4–1.50.56–1.7
Conjugated estrogens1.21.52.01.1–1.31.01.53.0–3.21.3–1.55.01.3–4.5
Equilin sulfate ? ?1.0 ? ?6.07.56.07.5 ?
Ethinylestradiol12015040060–150100400500–600500–6003502.9–5.0
Diethylstilbestrol ? ? ?2.9–3.4 ? ?26–2825–37205.7–7.5
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

See also: Pharmacokinetics of estradiol

Estropipate is hydrolyzed into estrone in the body.[10] Estrone can then be transformed into estradiol by 17β-hydroxysteroid dehydrogenase.

Chemistry

See also: Estrogen ester and List of estrogen esters

History

Estropipate was introduced for medical use by Abbott in 1968.[11] It was approved by the FDA in the United States in 1991.[12]

Society and culture

Generic names

Estropipate is the generic name of the drug and its INN, USAN, and BAN.[2][3][13][10][14]

Brand names

Estropipate is or has been marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.[14][2][13][10]

Availability

Estropipate appears to remain available only in the United States.[14] In the past, estropipate has also been marketed in Canada, the United Kingdom, Ireland, Switzerland, Australia, South Africa, Mexico, and Indonesia.[14][13][10] There is no manufacturer selling the medication in Canada as of 2021.[15]

References

  1. 1 2 3 4 5 6 7 8 9 "DailyMed - ESTROPIPATE tablet". dailymed.nlm.nih.gov. Archived from the original on 11 January 2022. Retrieved 17 December 2021.
  2. 1 2 3 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. Archived from the original on 27 June 2021. Retrieved 19 October 2020.
  3. 1 2 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.
  4. ↑ Report on Carcinogens: Carcinogen Profiles. Department of Health and Human Services, Public Health Service, National Toxicology Program. 2000. p. RA1-PA26. Archived from the original on 2022-01-11. Retrieved 2021-12-17.
  5. ↑ "Estropipate Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 17 December 2021.
  6. ↑ "Estropipate Prices and Estropipate Coupons - GoodRx". GoodRx. Retrieved 17 December 2021.
  7. ↑ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Archived from the original on 22 March 2021. Retrieved 19 December 2021.
  8. ↑ "Ogen, estropipate tablets, USP" (PDF). Pharmacia & Upjohn Co. U.S. Food and Drug Administration. December 2004. Archived (PDF) from the original on 2021-04-04. Retrieved 2020-10-19.
  9. ↑ 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. Archived from the original on 26 March 2019. Retrieved 19 October 2020.
  10. 1 2 3 4 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. Archived from the original on 2021-11-01. Retrieved 2020-10-19.
  11. ↑ Budoff PW (1 August 1983). No more hot flashes, and other good news. Putnam. p. 28. ISBN 978-0-399-12793-9.
  12. ↑ P & T. CORE Medical Journals. July 1993. Archived from the original on 2021-11-02. Retrieved 2020-10-19.
  13. 1 2 3 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1. Archived from the original on 2021-11-01. Retrieved 2020-10-19.
  14. 1 2 3 4 "Estropipate". Drugs.com. Archived from the original on 2019-08-24. Retrieved 2020-10-19.
  15. ↑ "Estropipate". www.dpic.org. Archived from the original on 16 April 2021. Retrieved 17 December 2021.
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