Estropipate

{{short description|Estrogen medication}}

{{Redirect|Ogen|the character in the Japanese anime|Ogen (Basilisk)|the melon cultivar|Galia melon}}

{{Drugbox

| Verifiedfields = verified

| verifiedrevid = 461095715

| 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

| image = Estropipate.png

| width = 250px

| image2 = Estropipate molecule ball.png

| width2 = 250px

| tradename = Harmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others

| Drugs.com = {{drugs.com|monograph|estropipate-esterified-estrogens}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

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| routes_of_administration = By mouth

| class = Estrogen; Estrogen ester

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 7280-37-7

| ATC_prefix = None

| ATC_suffix =

| PubChem = 5284555

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB04574

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4447610

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = SVI38UY019

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00948

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 4873

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1200980

| synonyms = Piperazine estrone sulfate; Estrone sulfate piperazine salt; Pipestrone

| C=22 | H=32 | N=2 | O=5 | S=1

| SMILES = O=S(=O)(O)Oc1cc4c(cc1)[C@@H]3[C@H]([C@@H]2CCC(=O)[C@@]2(C)CC3)CC4.N1CCNCC1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HZEQBCVBILBTEP-ZFINNJDLSA-N

}}

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.{{cite web | title = Ogen, estropipate tablets, USP | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf | work = Pharmacia & Upjohn Co | publisher = U.S. Food and Drug Administration | date = December 2004 }}{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA900|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=900–}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA114|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=114–}}{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd |url= https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1484|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1484–}} It is a salt of estrone sulfate and piperazine, and is transformed into estrone and estradiol in the body. It is taken by mouth.

Medical uses

Estropipate is used to:{{Additional citation needed|date=March 2018}}

{{Estrogen dosages for menopausal hormone therapy}}

=Available forms=

Estropipate was available in the form of 0.75, 1.5, 3, and 6 mg oral tablets and 1.5 mg/gram vaginal cream. Estropipate is no longer available in the United States.

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}}

=Pharmacokinetics=

{{See also|Pharmacokinetics of estradiol}}

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

Chemistry

{{See also|Estrogen ester|List of estrogen esters}}

History

Estropipate was introduced for medical use by Abbott in 1968.{{cite book| first = Penny Wise | last = Budoff | name-list-style = vanc |title=No more hot flashes, and other good news|url=https://archive.org/details/nomorehotflashes00budo_1|url-access=registration|date=1 August 1983|publisher=Putnam|isbn=978-0-399-12793-9|page=[https://archive.org/details/nomorehotflashes00budo_1/page/28 28]}} It was approved by the {{abbrlink|FDA|Food and Drug Administration}} in the United States in 1991.{{cite book|title=P & T.|url=https://books.google.com/books?id=51cVAQAAMAAJ|date=July 1993|publisher=CORE Medical Journals}}

Society and culture

=Generic names=

Estropipate is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|USAN|United States Adopted Name}}, and {{abbrlink|BAN|British Approved Name}}.{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA408|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=408–}}{{cite book | veditors = Sweetman SC |chapter=Sex hormones and their modulators |title=Martindale: The Complete Drug Reference |edition=36th |year=2009 |page=2101 |publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1|url=https://www.medicinescomplete.com/mc/martindale/2009/mg-9020-r.htm}}{{cite web | title = Estropipate | url = https://www.drugs.com/international/estropipate.html | work = Drugs.com }}

=Brand names=

Estropipate was marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.

=Availability=

Estropipate has been discontinued in the United States. In the past, estropipate has also been marketed in Canada, the United Kingdom, Ireland, Switzerland, Australia, South Africa, Mexico, and Indonesia.

References

{{Reflist}}

{{Estradiol}}

{{Estrogens and antiestrogens}}

{{Estrogen receptor modulators}}

Category:Estranes

Category:Estrone esters

Category:Ketones

Category:Piperazines

Category:Sulfate esters

Category:Salts

Category:Synthetic estrogens