{{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 = [(8''R'',9''S'',13''S'',14''S'')-13-Methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-3-yl] hydrogen sulfate; piperazine | image = Estropipate.png | image_class = skin-invert-image | width = 250px | image2 = Estropipate molecule ball.png | image_class2 = bg-transparent | width2 = 250px
<!--Clinical data--> | tradename = Harmogen, Improvera, Ogen, Ortho-Est, Sulestrex, others | Drugs.com = {{drugs.com|monograph|estropipate-esterified-estrogens}} | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status = | routes_of_administration = By mouth | class = Estrogen; Estrogen ester
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | 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
<!--Chemical data--> | 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.<ref name="OgenLabel">{{cite web | title = Ogen, estropipate tablets, USP | url = https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf | archive-url = https://web.archive.org/web/20170216163640/http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/083220s041lbl.pdf | url-status = dead | archive-date = February 16, 2017 | work = Pharmacia & Upjohn Co | publisher = U.S. Food and Drug Administration | date = December 2004 }}</ref><ref name="Elks2014">{{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–}}</ref><ref name="MortonHall2012">{{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–}}</ref><ref name="Publishing2013">{{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–}}</ref> It is a salt of estrone sulfate and piperazine, and is transformed into estrone and estradiol in the body.<ref name="Elks2014" /><ref name="MortonHall2012" /> It is taken by mouth.<ref name="OgenLabel" />
==Medical uses== Estropipate is used to:<ref name="OgenLabel" />{{Additional citation needed|date=March 2018}}
* Alleviate symptoms of menopause as menopausal hormone therapy * Treat some types of infertility * Treat some conditions leading to underdevelopment of female sexual characteristics * Treat vaginal atrophy * Treat some types of breast cancer (particularly in men and postmenopausal women) * Treat prostate cancer * Prevent osteoporosis
{{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.<ref name="Martindale" /> 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.<ref name="Budoff1983">{{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]}}</ref> It was approved by the {{abbrlink|FDA|Food and Drug Administration}} in the United States in 1991.<ref name="CORE1993">{{cite book|title=P & T.|url=https://books.google.com/books?id=51cVAQAAMAAJ|date=July 1993|publisher=CORE Medical Journals}}</ref>
==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}}.<ref name="Elks2014" /><ref name="MortonHall2012" /><ref name="IndexNominum2000">{{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–}}</ref><ref name="Martindale">{{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}}</ref><ref name="Drugs.com">{{cite web | title = Estropipate | url = https://www.drugs.com/international/estropipate.html | work = Drugs.com }}</ref>
===Brand names=== Estropipate was marketed under the brand names Genoral, Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others.<ref name="Drugs.com" /><ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Martindale" />
===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.<ref name="Drugs.com" /><ref name="IndexNominum2000" /><ref name="Martindale" />
== References == {{Reflist}}
{{Estradiol}} {{Estrogens and antiestrogens}} {{Estrogen receptor modulators}}
Category:Estranes Category:Estrone esters Category:Ketones Category:Piperazines Category:Organosulfates Category:Salts Category:Synthetic estrogens