Estropipate

Estropipate
Clinical data
Trade names Harmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others
Synonyms Piperazine estrone sulfate; Estrone sulfate piperazine salt; Pipestrone
AHFS/Drugs.com Monograph
Routes of
administration		 By mouth
Drug class Estrogen; Estrogen ester
ATC code
  • None
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.027.906 Edit this at Wikidata
Chemical and physical data
Formula C22H32N2O5S
Molar mass 436.56 g/mol
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]

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).[5]

Relative oral potencies of estrogens
EstrogenTypeHFVEUCaFSHLHHDL-CSHBGCBGAGTRatio
EstradiolBioidentical1.01.01.01.01.01.01.01.01.01.0
EstroneBioidenticalNDNDND0.30.3NDNDNDNDND
EstriolBioidentical0.30.30.10.3ND0.2NDNDND0.67
Estrone sulfateBioidenticalND0.90.90.90.90.50.90.71.50.56–1.7
Conjugated estrogensNatural1.21.52.01.11.01.53.01.55.01.3–4.5
Equilin sulfateNaturalNDNDNDNDND6.07.56.07.5ND
EthinylestradiolSynthetic120150401201004005006003502.9–5.0
DiethylstilbestrolSyntheticNDNDND3.4NDND25.624.519.55.7–7.5
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 hepatic proteins. Ratio = Ratio of liver protein effects to hot flashes relief and gonadotropin suppression. ND = No data. 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 naturally occur in animals or in the environment. Miscellaneous: Direct link to table. Sources: [6][7][8][9][10][11]

Pharmacokinetics

Estropipate is hydrolyzed into estrone in the body.[12] Estrone can then be transformed into estradiol by 17β-hydroxysteroid dehydrogenase.

Chemistry

History

Estropipate was introduced for medical use by Abbott in 1968.[13] It was approved by the FDA in the United States in 1991.[14]

Society and culture

Generic names

Estropipate is the generic name of the drug and its INN, USAN, and BAN.[2][3][15][12][16]

Brand names

Estropipate is or has been marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.[16][2][15][12]

Availability

Estropipate appears to remain available only in the United States.[16] In the past, estropipate has also been marketed in Canada, the United Kingdom, Ireland, Switzerland, Australia, South Africa, Mexico, and Indonesia.[16][15][12]

References

  1. 1 2 3 https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf
  2. 1 2 3 4 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. 1 2 3 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. ↑ http://www.fasebj.org/cgi/content/meeting_abstract/23/1_MeetingAbstracts/748.2
  6. ↑ Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947.
  7. ↑ Alfred S. Wolf; H.P.G. Schneider (12 March 2013). Östrogene in Diagnostik und Therapie. Springer-Verlag. pp. 78–. ISBN 978-3-642-75101-1.
  8. ↑ Manfred Kaufmann; Serban-Dan Costa; Anton Scharl (27 November 2013). Die Gynäkologie. Springer-Verlag. pp. 105–. ISBN 978-3-662-11496-4.
  9. ↑ Mashchak CA, Lobo RA, Dozono-Takano R, Eggena P, Nakamura RM, Brenner PF, Mishell DR (November 1982). "Comparison of pharmacodynamic properties of various estrogen formulations". Am. J. Obstet. Gynecol. 144 (5): 511–8. doi:10.1016/0002-9378(82)90218-6. PMID 6291391.
  10. ↑ Helgason S (1982). "Estrogen replacement therapy after the menopause. Estrogenicity and metabolic effects". Acta Obstet Gynecol Scand Suppl. 107: 1–29. doi:10.3109/00016348209155333. PMID 6282033.
  11. ↑ Lobo RA, Nguyen HN, Eggena P, Brenner PF (February 1988). "Biologic effects of equilin sulfate in postmenopausal women". Fertil. Steril. 49 (2): 234–8. doi:10.1016/S0015-0282(16)59708-8. PMID 3338581.
  12. 1 2 3 4 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.
  13. ↑ Penny Wise Budoff (1 August 1983). No more hot flashes, and other good news. Putnam. p. 28. ISBN 978-0-399-12793-9.
  14. ↑ P & T. CORE Medical Journals. July 1993.
  15. 1 2 3 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1.
  16. 1 2 3 4 https://www.drugs.com/international/estropipate.html


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