Estropipate

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Estropipate
Estropipate.png
Estropipate molecule ball.png
Clinical data
Trade namesHarmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others
SynonymsPiperazine 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
ECHA InfoCard100.027.906 Edit this at Wikidata
Chemical and physical data
FormulaC22H32N2O5S
Molar mass436.56 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[edit]

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

Pharmacology[edit]

Pharmacodynamics[edit]

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

Estrogen Type HF VE UCa FSH LH HDL-C SHBG CBG AGT Ratio
Estradiol Bioidentical 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0
Estrone Bioidentical ND ND ND 0.3 0.3 ND ND ND ND ND
Estriol Bioidentical 0.3 0.3 0.1 0.3 ND 0.2 ND ND ND 0.67
Estrone sulfate Bioidentical ND 0.9 0.9 0.9 0.9 0.5 0.9 0.7 1.5 0.56–1.7
Conjugated estrogens Natural 1.2 1.5 2.0 1.1 1.0 1.5 3.0 1.5 5.0 1.3–4.5
Equilin sulfate Natural ND ND ND ND ND 6.0 7.5 6.0 7.5 ND
Ethinylestradiol Synthetic 120 150 40 120 100 400 500 600 350 2.9–5.0
Diethylstilbestrol Synthetic ND ND ND 3.4 ND ND 25.6 24.5 19.5 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 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. Sources: [6][7][8][9][10][11]

Pharmacokinetics[edit]

Estropipate is hydrolyzed into estrone in the body.[12] 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.[13] It was approved by the FDA in the United States in 1991.[14]

Society and culture[edit]

Generic names[edit]

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

Brand names[edit]

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[edit]

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[edit]

  1. ^ a b c https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf
  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. ^ 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. ^ 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.
  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. ^ a b c Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 408–. ISBN 978-3-88763-075-1.
  16. ^ a b c d https://www.drugs.com/international/estropipate.html